If you’re an early stage startup, you’re probably leaning heavily into outbound. And that makes sense. It’s the fastest motion to stand up. You don’t need to wait for SEO or other digital marketing to compound, or for a partnership ecosystem to mature. You can start right now.

But here’s the problem: most startups run outbound like they are playing darts at a bar - drunk. Build a big list, blast a sequence (with terrible copy), and hope for the best. And at a ~1% average conversion rate on cold outbound, you need a LOT of volume to make that math work — volume that will kill your domain reputation real freaking fast.

The fix isn’t to abandon outbound. It’s to get smarter about which accounts you spend time on.

There are two great ways to do this:

1. Account-based marketing (ABM) — a coordinated, multi-channel approach where marketing and sales align around a defined set of named accounts with personalized campaigns and content.

2. Signal-based outbound — equipping your sales team with real-time buying signals so they know which accounts to prioritize and when to reach out.

If you can combine the two, even better.

ABM builds awareness and air cover with your target accounts while signal-based outbound ensures your reps are spending their time on the accounts most likely to convert - right now. Together they create a continuous loop — marketing warms the account, signals tell you when it’s ready, and sales moves on it with context.

We’ll go deeper on ABM later this month. For now, let’s start with the foundation both approaches depend on: understanding which signals actually matter for your business.

Signal-based GTM: what it is and how to get started

Start with your own signal profile

Every business has a different set of signals that predict buying behavior for their product. The mistake I see founders make is jumping straight to tools and data sources before spending the time to understand what signals actually matter for their product and ICP.

Here’s a simple exercise: look at your last 10 closed-won deals and ask yourself (or them) what happened right before those accounts entered your pipeline.

Did they just go through an acquisition? Hire a new leader in the function you sell into? Have a cyber incident? Recent revenue growth or decline? Kick off a relevant initiative?

There’s almost always a pattern. That pattern is your signal profile, and it should drive every decision about what you track and where you invest.

If you skip this step, you’ll end up monitoring signals that look smart on paper but don’t actually correlate with buying behavior for your specific business. A Series A announcement might be a strong signal if you sell SOC2 compliance software. It might mean nothing if you sell accounting software.

Do this exercise before you do anything else.

First-party signals: start here if you can

First-party signals are the buying indicators happening inside your own ecosystem — website visits, content downloads, email engagement, product usage, CRM activity. They’re the highest quality signals you have because they reflect direct interaction with your brand.

If someone visits your pricing page three times in a week, that’s a better signal than almost anything a third-party tool can tell you.

The challenge for most early-stage startups is volume. If you’re getting 500 website visitors a month and you have 200 contacts in your CRM, your first-party data alone isn’t going to fill a pipeline. It should absolutely be tracked and acted on — set up alerts in HubSpot for pricing page visits, track email engagement, pay attention to who’s opening your proposals more than once. But it probably can’t be your only signal source yet.

Think of first-party signals as your highest-fidelity layer. You want them running in the background at all times. But keep in mind — by the time someone lands on your pricing page, something already changed inside their business that sent them looking.

Maybe they hired a new leader who’s reevaluating the stack. Maybe they just closed a funding round and now have the budget. The first-party signal you’re seeing is often the result of a third-party signal you missed.

Which means even if you have strong first-party data, supplementing with external signals lets you get in front of accounts earlier in the buying cycle — before they’re on your pricing page and your competitor’s too.

Third-party signals: filling the gap

This is where most early-stage teams need to focus their energy — buying signals happening outside your ecosystem that suggest an account might be entering a buying cycle.

The good news is there’s a growing landscape of tools that make these signals accessible without a massive budget:

Job changes and org moves. When a company hires a new VP of Sales or a new Head of Marketing, there’s often a 90-day window where that new leader is evaluating their stack and making changes. Apollo, LinkedIn Sales Navigator, and plenty of other tools make it easy to track these moves across your target accounts.

Funding events. A company that just raised a Series A or B often has budget earmarked for building out the exact functions you sell into. Crunchbase or Pitchbook are the most well-known sources here — you can set up alerts for funding rounds in your target segments.

Tech stack changes. If you sell a product that integrates with or replaces specific tools, knowing when a target account adds or drops a technology is a strong signal. Apollo, ZoomInfo and others allow you to track technographic data.

Category or competitor research. When a company starts actively researching your category or a competitor — reading G2 reviews, comparing vendors, visiting competitor profiles — that’s about as close to a hand-raise as you’ll get for outbound. G2 Buyer Intent data surfaces this activity.

Each of these gives you a lens into a different type of buying behavior. And most offer free tiers or affordable plans that work at startup scale.

Where individual signals fall short

Here’s the catch with everything I just described: each signal in isolation can get noisy.

A company raising a Series B doesn’t mean they’re buying your product. A VP hire doesn’t mean they’re evaluating your category. A G2 visit could be a bored analyst doing a competitive landscape for their boss.

The real power of signal-based GTM isn’t tracking individual data points. It’s layering and correlating them.

When you see a target account that just raised funding AND hired a new leader in your function AND started researching your category on G2 AND visited your website twice this month — that’s a fundamentally different signal trail than any single one of those events alone. That example account is almost certainly a buyer – right now.

The problem is that manually cross-referencing all of these sources is brutal. You’re logging into five different platforms, exporting CSVs, trying to match company names across inconsistent data sets. It’s not sustainable or scalable.

This is the exact problem we built ABM Intel to solve — pulling these signal layers together into a single view so you can see which accounts are actually heating up right now, not just which ones match your firmographic criteria. If you’re running an outbound-heavy motion and want to skip the manual correlation work, it’s worth a look.

But even without tooling for the correlation layer, the principle holds: stacking multiple signals is exponentially more predictive than any single one. And not all signals are created equal – figure out which ones matter the most for your sales cycle.

Signals are a GTM multivitamin

One thing I want to close with — and this is a framework I come back to constantly with my clients — you need to focus your investments on GTM multivitamins.

Signal-based GTM shouldn’t just be an outbound play.

The same signals that tell your SDR or AE which accounts to prioritize this week also tell your marketing team where to focus ad spend. They also inform your CS team which existing customers might be ready for an expansion conversation.

One investment in understanding and tracking buying signals can pay off across every function in your GTM motion. For a resource-constrained startup, that kind of leverage is everything.

Start with your signal profile. Layer in what you can afford. Act on what the data tells you. Watch your conversion rates soar.

P.S. We just started offering GTM Engineering services, too. This is the exact kind of infrastructure and automation a GTM engineer can help you build to scale.

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups, we serve as your Fractional GTM executive or engineer. Learn more about -

• My approach to client engagements

• My engagement models and pricing

• What is a GTM engineer?

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

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Before we dive in this week, I want to leave you with a reminder that I think is worth a call out: it’s easy to get caught up chasing new logos. New logos, new leads, new people — it’s exciting, it’s visible, and it tends to be where founders focus most of their energy.

But for many companies, the fastest path to growth isn’t new logo acquisition. It’s retaining and expanding the customers you already have. They already trust you. They’ve already seen value. The cost to grow them is a fraction of what it costs to replace them.

Don’t lose sight of that. And if there’s one practice that anchors a strong retention and expansion motion, particularly with larger more complex or enterprise customers, it’s the QBR — when it’s done right.

Here’s how to do it right.

How to run a QBR at early stage (and make it worth everyone’s time)

The quarterly business review has a reputation problem. Mainly because the ones many of us have experienced were 45-minute slide decks summarizing data we could have read in an email.

However - done right, a QBR is one of the highest-leverage touchpoints in your entire customer journey. It’s where you reinforce value, surface risk before it becomes churn, and open expansion conversations in a way that feels like helping rather than selling. Done wrong, it’s a calendar invite your customer dreads and starts declining.

Here’s how to do it right — including when it actually makes sense to do it at all.

Not every customer needs a QBR

A QBR is a significant investment — in prep time for you, in the customer’s calendar, in the relationship capital required to get senior stakeholders in the room. It only makes sense for the customers where that investment is proportionate to the commercial value or opportunity.

The way to think about this isn’t a hard ACV threshold. It’s your tier one customers — whoever is commercially most important to your business. For most early-stage companies, that’s roughly the top 30% of your customer base by revenue or strategic value. Those are the accounts that warrant a structured quarterly conversation. The rest of your book can be served with lighter-touch check-ins, standard reporting, automated health score monitoring, and reactive support.

If you sell exclusively to enterprise organizations, this calculus changes — nearly every customer is likely tier one, and QBRs should be a standard part of your CS motion for all of them.

But if you have a mixed book spanning SMB through mid-market, be deliberate. Running a formal QBR with a customer on a small contract is usually not the right use of anyone’s time.

A few variables that could pull a customer into QBR territory regardless of ACV: they’re a strong reference or expansion candidate; they’re coming up for renewal and the relationship is frayed; or there’s a risk signal that warrants a more structured conversation.

What a QBR is not

Before getting into the agenda, it’s worth being clear on what you’re not trying to do...

• A QBR is not a status update. If the customer wanted a usage report, you could have emailed it.

• It’s not a product demo of features they haven’t adopted yet — that feels like a sales call in disguise.

• And it’s not a support ticket retrospective, which signals that the relationship is reactive rather than strategic.

The posture you want going in is: we’re here to talk about your business, review whether we’re delivering the value we committed to, and make sure the next quarter sets you up for the outcomes you care about.

That’s a different conversation than “here’s your dashboard from the last 90 days.”

Who should be in the room

On the customer side, you want their day-to-day champion — the person who uses the product and can speak to the operational reality — and ideally their manager or economic buyer.

Also, getting a senior stakeholder back in the conversation at least once a year is one of the most important things CS can do for retention and expansion. They were in the room when the decision was made. They remember what was promised. And they’re the ones who will sign the renewal. Make sure they aren’t completely out of the loop before that renewal hits their inbox.

On your side, the CS lead should typically own the QBR. But if there’s an active expansion opportunity or the renewal is coming up, having an AE or Account Manager join the call is a good move — it signals investment in the account and keeps the commercial relationship warm without making the whole conversation feel like a sales call.

Getting the customer to actually show up

The invite is the first impression of the QBR, and most of them are bad. A calendar hold that says “Q3 Business Review” with no context gives the customer nothing to look forward to and every reason to reschedule when something else comes up.

Getting the right people in the room — especially a senior stakeholder who isn’t part of the day-to-day usage — requires a bit more intentionality than a generic calendar invite.

Consider renaming it. “QBR” is internal language that means nothing to most customers, and for some it carries baggage from bureaucratic enterprise relationships they’ve been through before. “Strategy session,” “quarterly growth review,” or simply “[Your company] + [Their company] — Q3 review” all land warmer and signal that this is a conversation, not a presentation.

Lead the invite with a TLDR of why they should care. Before the customer even decides whether to accept, give them a reason to be excited. A short note alongside the calendar invite that surfaces two or three concrete wins from the quarter — in their language, not yours — immediately reframes the QBR from obligation to opportunity.

Something like: “Your team hit [X milestone] this quarter, and [cost/time savings] are estimated to be [X]. I also want to share a couple of developments on our end that are directly relevant to [their stated goal]. Would appreciate 45 minutes to walk through it together — I’ll send an agenda in advance.”

Specific, forward-looking, and clearly about them. If there’s a meaningful product update that applies to their use case, call it out by name. Customers are much more likely to accept an invite when they feel like there’s something in it for them before they even get on the call.

Send the agenda ahead of time. Following up with a brief agenda a few days or even a week before the call does two things: it helps the customer prepare any context, data, or questions they want to bring, and it removes the anxiety of not knowing what they’re walking into. It also signals that you’ve prepared — which raises their confidence that the time will be well spent. The downloadable agenda template linked at the end of this article is designed to serve this purpose.

Make the ask for the senior stakeholder personal. If you want the economic buyer in the room, don’t leave that to the day-to-day champion to sort out. CS or the AE should reach out directly:

“We’d appreciate the opportunity to reconnect with [exec name] for this one — it’s been a few quarters since we’ve had a chance to connect, and I want to make sure we’re aligned on where things are headed.”

A direct, personal ask is much harder to deflect than a generic calendar invite sent through a gatekeeper.

Get it on the calendar early. Don’t send a QBR invite two weeks out and expect to get a senior stakeholder. Four to six weeks of lead time is reasonable to coordinate across multiple calendars and senior execs — it signals that this is a planned, intentional touchpoint, not a reactive check-in. Build the scheduling trigger into your CS calendar so it’s not something you have to remember.

If a customer consistently declines or reschedules QBRs, that’s a health signal in itself — and worth addressing directly rather than just rescheduling again. Sometimes the right move is a softer conversation first:

“I want to make sure we’re making this time valuable for your team — is there anything we should do differently for this next session?”

The agenda that actually works

A QBR should run 45 to 60 minutes. Any shorter and it’s hard to have a real conversation; any longer and you’re testing their patience. The downloadable agenda template gives you a timed structure you can adapt — here’s the logic behind each section.

Open with their world, not yours. The first five minutes should be a genuine check-in: what’s changed for them since you last spoke? New priorities, leadership changes, upcoming initiatives? This does two things — it shows you’re interested in their business beyond the contract, and it surfaces context that shapes everything else in the call.

Tip: Do your homework to attempt to identify these things before the call, too. If you can locate any of this type of news beforehand, reframe your opener accordingly:

“We saw that you have a new CFO / announced an expansion into EMEA / [insert any other news you found]. We'd love to learn more about that. Any other updates we might not have seen?”

Review progress against their goals. This is the heart of the QBR and the section that requires the most prep. Go back to what was documented at kickoff — or in the sales-to-CS handoff — and hold the conversation against those original commitments. What did they say success looked like in 90 days? In 12 months? What’s been achieved, what’s behind, and why? Use their metrics where possible.

Cover product usage and value delivered. Walk through the numbers, but translate them into business language. “You processed 4,200 events this quarter” means less than “your team is handling roughly 350 more events a month than when you started — here’s what that represents in time saved.” Frame the value in terms that connect to the outcomes they told you they cared about.

Share what’s new or coming on your end. A brief section on relevant product enhancements or roadmap items — emphasis on relevant. Not a full product roadmap dump, but a targeted look at what you’ve delivered or what’s coming that applies to their use case. This is also a good moment to point them to your help library and any new documentation or resources that can support their team.

Have the forward-looking conversation. This is where expansion lives, and the key is that it has to emerge from the goals conversation rather than feeling like a pivot to sales mode. If they said at kickoff that they wanted to expand to three teams and they’re only on one, that’s not a sales conversation — that’s you helping them get the value they told you they wanted. The downloadable template includes specific prompts for common expansion scenarios.

Close with clear actions. Before you leave the call, recap who owns what and by when — on both sides. This is what makes the follow-up email useful rather than performative, and it sets the tone for the next quarter.

The expansion conversation

The biggest mistake CS teams make in QBRs is either skipping the expansion conversation entirely — leaving money on the table — or tacking it on at the end in a way that feels like a gear shift.

The setup is everything. If you’ve spent 40 minutes genuinely reviewing their business, discussing their goals, and demonstrating value in their language, the expansion conversation is a natural extension, not a mood change. “You mentioned wanting to roll this out to your operations team — is that still on the roadmap for you this half?” doesn’t feel like a sales pitch when it’s rooted in something they told you months ago.

The expansion prompts in the agenda template cover the most common scenarios: a goal they set that they haven’t yet achieved, a feature they’re not using that would clearly benefit them, an adjacent team or use case that’s come up in conversation, and the renewal conversation itself.

None of them require hard selling. They require good notes from the kickoff call and the discipline to bring the customer’s own words back into the room.

Preparing without it taking all day

The prep is what separates a QBR that feels sharp from one that feels generic — and it doesn’t have to take hours. If your CRM is well-maintained, you’re using call recording software, and you’re tracking usage data, most of what you need is already somewhere findable.

Pull your usage data and support ticket summary. Review the original goals from the kickoff or last QBR call recording. Check for any open action items from the previous conversation. Note the renewal date and any commercial context worth being aware of. If you’ve collected an NPS score this period, have it ready.

Use AI to help synthesize the narrative. Drop all your files into Claude or ChatGPT and ask it to identify the key themes — what’s going well, what’s at risk, what hasn’t moved. What comes back is a useful first draft of the story you want to tell on the call, which you then refine with your own judgment about the relationship.

After the call

Send a follow-up email within 24 hours summarizing key wins, any outstanding challenges, and all agreed action items with owners and dates. This is not optional — it’s what makes the QBR feel like a professional, structured touchpoint rather than a nice chat.

Update your CRM with notes, any expansion flags, and the current renewal outlook. And set a reminder for the next QBR before you close the record. The cadence compounds: customers who experience a consistent, well-run quarterly conversation are meaningfully less likely to churn than those who only hear from CS when something goes wrong.

👉 Download the QBR agenda template — includes a pre-call prep checklist, timed agenda with facilitator prompts, expansion conversation guide, and post-call follow-up checklist.

QBR Agenda Template

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

Subscribe for weekly education, ideas, and frameworks

In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

Subscribe now

1. A customer self-service tool

2. A sales enablement asset

3. An SEO/AEO contribuitor

…and so much more. If you’re wondering…what the heck does she mean by help library - here is an example. Enjoy.

Your help library is a GTM multivitamin (here’s how to build one)

Most early-stage startups treat their help documentation as an afterthought. Something to throw together when the support queue gets too long, or when a new hire asks a question for the fifth time and someone finally decides to write it down.

That’s a missed opportunity — because a well-built help library isn’t just a support tool. It’s the foundation your entire customer support motion is built on, including AI.

Before we get into structure and tooling: if you ever want AI to help answer your customers’ questions automatically, you need a help library first. That’s what the AI trains on. No content, no AI. Which means every article you write today is also an investment in a smarter, more scalable support experience when you’re ready.

Beyond AI enablement, a help library accelerates your sales cycle, reduces CS workload, accelerates customer onboarding, supports your SEO/AEO strategy, and helps new team members ramp faster. All from the same body of work.

That’s what I mean when I call something a GTM multivitamin — when you’re resource-constrained, single-purpose activities are a luxury you can’t afford.

Why most startup help libraries fail

The typical pattern: a founder or early CS hire creates a Google Doc with some FAQs, sends it as a link in an onboarding email, and never touches it again. Six months later it’s out of date, no one can find it, and the same questions are still landing in the support inbox.

The problem usually isn’t effort — it’s structure. A help library that actually reduces CS load has three things the Google Doc or folder doesn’t:

1. it’s searchable,

2. it’s organized around how customers think (not how your product is built), and

3. someone owns keeping it current.

Start with your top 10 support questions

The single best place to start is answering the 10 questions your team answers most often. Not the most complex ones, not the ones you think customers should be asking — the ones that actually land in your inbox on repeat.

Here’s the fast way to find them: use AI.

Pull your last 90 days of support tickets, onboarding call transcripts, and/or customer emails and drop them into Claude or ChatGPT with a simple prompt:

“Analyze these and identify the 10 most frequently asked questions or recurring topics.”

If you’re using a call recording tool like Fireflies or tl;dv, pull transcripts from your customer and sales calls and run the same analysis. What comes back is usually more accurate than what you’d reconstruct from memory, and it takes minutes instead of an afternoon.

Those top 10 become your first 10 help articles — and they’re exactly what your AI chat tool will be asked first. A well-written article on each one means the AI can deflect those questions automatically, without a human ever getting involved.

Recurring questions also tell you something important about your product: if the same issue keeps surfacing, that’s a signal worth routing to your product team as a UX or onboarding gap.

Once you have your first 10, expand from there. Aim to add 3-5 new articles a month.

A useful taxonomy for early-stage B2B products usually covers:

1. Getting started

2. Core features and how-tos

3. Integrations

4. Account and billing

Typically 30–50 articles total to cover your most common ground. A knowledge base of that size gives an AI tool enough content to handle the majority of incoming questions without human escalation.

Where your help library should live

My recommendation is straightforward: if you’re already using HubSpot for your CRM, use HubSpot Service Hub (Professional). If you’re not, Help Scout is a strong alternative. Both are purpose-built for customer-facing support, both have AI-powered chat built in, and both are right-sized (and priced) for early-stage companies.

HubSpot Service Hub is natively available within your CRM, ticketing, and live chat — so when a customer submits a ticket, relevant articles surface automatically. The AI chat feature uses your knowledge base to attempt an answer before routing to a human, deflecting a significant volume of preliminary questions. Articles live on a public URL and are indexed by Google, contributing to your SEO/AEO without any additional setup. Note that the Knowledge Base feature is available on Service Hub Professional and above, so confirm your plan.

Help Scout is my recommended alternative for teams not on HubSpot. Their product powers the knowledge base, and it works in tandem with their AI-powered chat which serves relevant articles before connecting a customer to a human. If the AI can’t resolve the question, the customer can ask to speak to someone directly. Clean, well-priced for small teams, and a gentler learning curve than most support platforms. Bonus - you can start for free, too.

Both tools operate on the same core logic: the AI scans your knowledge base, serves the most relevant answer, and only escalates to your team if it can’t resolve the issue. Deflection rates on well-documented topics are genuinely high — which is exactly why content quality matters. Thin or outdated articles mean the AI has nothing useful to surface, and your team ends up answering the same questions anyway.

The SEO/AEO angle most teams ignore

A public help library is one of the most underrated SEO/AEO plays available to an early-stage company. When you publish help articles on a public URL, you’re creating content Google (and LLMs) can index and surface to people searching for exactly those things — people who may discover your product as a result.

As I covered in SEO 101 for startups, the highest-value SEO content answers questions your ICP is already asking. Your top 10 support questions are, almost by definition, questions your customers are typing into Google. That’s a free content strategy hiding inside your support queue.

A few things that help your articles rank:

• use plain language in titles (match how customers phrase the question, not internal jargon),

• keep each article focused on one topic, and

• link between related articles to build topical depth.

No SEO/AEO specialist required — just intentionality.

How your help library helps you close deals

Here’s a benefit most founders don’t think about until someone points it out: your help library doesn’t just serve customers — it also serves prospective buyers who haven’t signed yet.

Think about what a prospect is doing in the final stages of evaluating your product. They’re trying to answer two questions: does this actually work, and how quickly can my team learn how to use it?

A well-built, publicly accessible help library answers both. It signals that the product is mature enough to have real documentation, that other customers are using it deeply enough to generate common questions, and that your company is invested in customer success beyond the sale.

You can use it actively in your sales process too. Before a final demo or proposal call, send a link to your getting started guide or a relevant how-to article. When a prospect raises a concern about implementation complexity, point them to the documentation. If a specific integration comes up in an evaluation, share the article that walks through exactly how it works. Done right, your help library functions as a self-serve proof point — one that builds confidence.

This is especially useful for buyers who do their own research outside of vendor conversations, which Gartner’s 2025 Software Buying Trends research confirms is the majority. When a prospect is digging around your website between calls, a thorough help center says something your marketing pages can’t: that real customers use this product, have real questions about it, and can get real answers fast.

How a help library reduces CS load over time

Every question your help library answers is a question your CS team doesn’t have to — whether that answer comes from a customer finding the article themselves, or from your AI chat surfacing it automatically.

Customers who can self-serve don’t submit tickets, freeing your CS team for high-value conversations. Onboarding calls can point to specific articles rather than covering everything live, shortening time-to-value. And new hires ramp faster because the answers exist somewhere findable. As your knowledge base grows, your AI chat tool gets smarter — broader coverage means higher deflection rates and a lighter lift for your team over time.

Keeping it current

A help library that goes stale does more harm than good — a customer who follows outdated instructions and gets stuck is worse off than if they’d just emailed support. And stale content is equally damaging for AI: if the articles are wrong, the AI’s answers will be wrong too.

Assign one person to own the help library. At early stage, this is usually the CSM or whoever runs onboarding. Their job isn’t to write everything — it’s to ensure articles get updated when the product changes and gaps get flagged when new questions surface.

Build a simple trigger into your process: any time a product update ships that changes a customer-facing workflow, the help library update is part of the launch checklist, not an afterthought. Additionally, mark your calendar for a thorough end-to-end review once a quarter.

What this unlocks as you grow

A well-maintained help library lets you serve more customers without adding CS headcount linearly. It makes AI-supported chat actually work — because the content is there, organized, and accurate. And it signals to customers that you’re invested in their success beyond the sales process.

If you’re building out your CS function more broadly — thinking through when to hire your first CSM, or how to structure the sales-to-CS handoff — a help library is the connective tissue that makes those investments land. The best onboarding in the world is still incomplete if customers have nowhere to go when a question comes up after the kickoff call.

Start with 10 articles. Choose HubSpot Service Hub if you’re already there, or Help Scout if you’re not. Make it public. Assign someone to own it. That’s enough to get the multivitamin working — and to lay the groundwork for AI to start pulling its weight in your support queue.

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

Subscribe for weekly education, ideas, and frameworks

In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

Subscribe now

So far we’ve covered:

• When to hire your first CSM

• The MVP for customer success

Next up - the Sales to CS handover. Enjoy.

The sales-to-CS handoff: what to document and how to use AI to do it faster

You closed the deal. The contract is signed. Champagne emoji in Slack.

And then… the customer gets introduced to your CS or operations team, who have almost none of the context your sales team spent months gathering. Cue the awkward “can you tell us a little about your goals?” email that makes the customer wonder if anyone was paying attention.

The sales-to-CS handoff is one of the most common failure points I see across early-stage startups. Not because teams don’t care — they do — but because there’s no structured process for transferring what was learned in the sales cycle into the hands of the people responsible for delivering on it.

Here’s how to fix that, including a shortcut that makes building a comprehensive handoff document much faster than you’d expect.

Why the handoff breaks down

In the early days, the founder usually owns both sales and customer success. They close the deal and they onboard the customer. All the context lives in one brain.

The problem surfaces when you start separating those functions — whether that’s hiring a first AE, a first CSM, or both. Suddenly, the person who sold the deal and the person responsible for delivering value are different people. And if there’s no formal transfer of information, your new customer will feel it immediately.

The most common symptoms:

• CS asks the customer to repeat information they already gave during the sales process

• Expectations set in the sales cycle don’t match what implementation sets up

• Red flags that surfaced in discovery (budget constraints, internal politics, technical limitations) disappear between handoff and onboarding

• The customer’s definition of “success” is vague because no one documented it clearly during the sales process

What a strong handoff document covers

A good handoff document isn’t a CRM dump. It’s a narrative brief that gives your CS or implementation team everything they need to walk into the kickoff call as if they’d been part of the sales process from day one.

Here’s what should be in it:

• Company and deal overview Basic context: company name, industry, size, HQ, the problem they were trying to solve, and what ultimately drove them to buy. Include the total contract value, contract start and end date, renewal date, and any relevant commercial terms worth flagging (e.g., performance clauses, expansion commitments, pilot terms).

• Stakeholder map List every person involved — name, title, role in the buying process, and their level of influence. Identify the economic buyer, the day-to-day champion, and any skeptics or detractors you encountered. Note who should be invited to the kickoff and who the CS team should prioritize building a relationship with.

• The “why now” and pain points What was the trigger that led them to start looking for a solution? What pain were they trying to solve? What had they tried before, and why didn’t it work? This context shapes how CS frames value conversations going forward.

• Goals and success criteria This is the most important section, and the most commonly missing one. What does success look like to this customer in 90 days? In 12 months? What metrics are they trying to move? If you can’t answer this from your sales process, that’s a signal to get more specific before the deal closes — not after.

• Product use case and configuration notes What are they actually using the product for? What specific features or workflows are core to their use case? Are there any custom configurations, integrations, or technical requirements discussed during the sales cycle? Flag anything that will affect onboarding complexity.

• Competitive context Who else were they evaluating? What made them choose you over the competition? This matters because it shapes the customer’s expectations — if they chose you specifically for a feature or capability, CS needs to know that.

• Risk flags and sensitivities This is the section that rarely gets documented and causes the most damage. What objections came up during the sales cycle? Are there internal stakeholders who weren’t fully bought in? Budget constraints that might affect expansion? Timelines that are under pressure? Surface it now so CS isn’t caught off guard.

• Commitments made during the sales process If the sales team made any specific promises — about implementation timelines, feature roadmap, support response times, introductions to the executive team — write them down. These verbal commitments have a way of coming up in kickoff calls, and CS needs to know they exist.

• Agreed next steps and onboarding plan What has already been communicated to the customer about what happens after signing? What’s the expected kickoff timeline? Who owns scheduling it?

Sales to CS Handover Template

How to use AI and call recording to build this faster

Here’s where the shortcut comes in.

Most of what goes into a great handoff document already exists — it just lives in your sales calls and your CRM. If you’re using a call recording tool like Fireflies, Fathom, or tl;dv during your sales process (and if you’re not, this is your sign to start), you have a complete record of every discovery call, demo, and negotiation conversation.

Once the deal closes, you have two powerful inputs to feed into an AI tool to produce said summary:

1. Your call recordings. Pull the transcripts or AI-generated summaries from your sales calls and ask an AI tool to extract key pain points and goals, stakeholder names and roles, objections and concerns, technical requirements, and the customer’s stated definition of success.

2. Your CRM data. This is one that most teams overlook. HubSpot has native connectors with both ChatGPT and Claude, which means you can pull deal data, contact records, notes, and activity history directly into a prompt without manually copying anything out. Combined with your call summaries, this gives you a remarkably complete picture of the deal.

The prompt is straightforward: provide both inputs, reference the sections of your handoff template, and ask the AI to populate each section based on what it finds. What comes back is a comprehensive first draft — often more thorough than what a rep would write manually, because it’s grounded in what was actually said and documented rather than reconstructed from memory under time pressure.

Done well, this whole process — pulling your inputs, running the prompt, reviewing and filling any gaps — should take no more than 10 minutes per deal. Your AE reviews the output, adds anything the calls and CRM don’t capture (nuanced sensitivities, verbal commitments made off-call, competitive intel), and the document is ready to hand off.

This approach has two benefits beyond just saving time.

• First, it makes the handoff document more objective — it’s grounded in what the customer actually said, not what the rep remembers.

• Second, it creates a feedback loop: when CS regularly has access to this level of deal detail, they’re in a much stronger position to flag risk early and drive toward the outcomes the customer articulated during the sales process.

Who owns what

A handoff document is only as good as the process around it. Here’s a simple ownership model:

• AE or founder (seller): Responsible for completing the handoff document before the kickoff call. Not after. This should be a hard close requirement — the deal isn’t “done” until the handoff is done.

• CS or implementation lead: Responsible for reviewing the document before the kickoff call and flagging any gaps back to the AE before getting on the phone with the customer.

• Both: Attend the kickoff call together, at least for the first few customers or until the handoff process is well-established. It signals continuity to the customer and gives CS a chance to fill in nuance in real time.

Making it stick operationally

Build the handoff document into your CRM as a required field or attachment before a deal can move to “Closed Won.” In HubSpot, this is easy to set up as a deal property or an associated task that blocks stage progression.

If you’ve built out a sales playbook, the handoff document template belongs in it — alongside your discovery framework, so reps know from day one that they’re gathering this information throughout the sales process, not scrambling to reconstruct it after the deal closes.

And if you’re still in a founder-led sales motion — managing both the sell and the onboard yourself — now is a good time to start documenting anyway. The habit you build now will make the transition to a dedicated CS team significantly smoother when you get there. (If you’re thinking through when that is, check out my earlier piece on when to hire your first CSM.)

The goal is simple: your new customer should never have to repeat themselves. Everything they told you during the sales process should travel with them into the relationship. That’s the standard a good handoff makes possible.

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

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In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

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When you’re the first CS hire at a startup, the list of things that need to get done can feel overwhelming. There’s no playbook, no existing processes, and probably a few fires already burning. The temptation is to try to fix everything at once—or worse, to just react to whatever’s loudest.

Don’t do that.

Instead, think about building a minimum viable product for customer success. What’s the smallest set of foundations that will have the highest impact on retention and customer experience? Get those right first, then iterate.

Here’s where to start.

The MVP for customer success

1. Understand the current state

Before you build anything, you need to know what you’re working with.

Audit existing onboarding. Walk through the current onboarding experience as if you were a new customer. What’s working? Where do people get stuck? Talk to recent customers about their onboarding experience—what confused them, what they wished they’d known sooner, what almost made them give up. Also — what can be automated or streamlined?

Talk to to the team. The founder, the CTO, the product team. What do they do today to service customers? What do they know they should be doing…but haven’t had time yet? Get as much history on the existing customer base as you can.

Analyze churn. If customers have already churned, do post-mortems. Talk to them if you can. Look for patterns: Did they fail to onboard properly? Did they lose their internal champion? Did they never really have a good use case to begin with? Understanding why people leave is the fastest way to figure out how to prevent it.

Talk to current customers. Especially the ones who are thriving. What did they do differently? What value are they getting that others might be missing? These conversations will shape everything else you build.

This discovery phase shouldn’t take months—a few weeks of focused conversations and analysis will give you what you need to prioritize.

2. Build the foundation

Once you understand the current state, start putting basic infrastructure in place.

Implement a shared inbox. Customer requests are probably scattered across founder emails, Slack DMs, and random channels. Centralize everything into a shared inbox (HubSpot if you already use that as your CRM - or Help Scout is a great alternative if not). This gives you visibility into the volume, response times, and common issues. You can’t improve what you can’t see.

Create a renewal calendar. Know exactly when every customer renews and build trigger points for outreach at 90, 60, and 30 days out. Renewals should never be a surprise—for you or for the customer.

Build a basic health score. This doesn’t need to be sophisticated. Start with a simple red/yellow/green framework based on a few signals: product usage frequency, support ticket volume, last engagement with your team, NPS response. The goal is to know who needs attention before they start looking for alternatives.

Segment your customers. Not every customer needs (or wants) the same level of service. Segment based on ACV, strategic importance, or complexity. A simple three-tier model works for most early-stage companies:

• Tier 1 (high-touch): Your largest or most strategic accounts. Monthly check-ins, quarterly business reviews, dedicated attention.

• Tier 2 (medium-touch): Solid mid-tier accounts. Quarterly check-ins, proactive outreach around renewals and major product updates.

• Tier 3 (low-touch): Smaller accounts or those with simple use cases. Primarily self-serve with reactive support.

Your segmentation will evolve, but you need a starting point to allocate your time effectively.

3. Create leverage

As a team of one (or close to it), you need to create systems that scale beyond your personal bandwidth.

Build a public knowledge base. This is what I call a GTM multivitamin—it does multiple jobs at once:

• Self-service for customers. Many customers prefer finding answers themselves rather than waiting for a response. A good knowledge base reduces support volume and improves customer experience simultaneously.

• AI chatbot training. If you implement a support chatbot (or plan to), your knowledge base becomes the data that trains it. The better your documentation, the more questions AI can handle without human intervention.

• SEO and AEO. Help content ranks well in search and feeds AI answer engines. Prospects researching solutions often land on help docs—and seeing clear, comprehensive documentation builds confidence that they won’t be left stranded post-purchase.

• Sales enablement. Sales can point prospects to your knowledge base as proof that you take customer success seriously. “Here’s exactly how our product works” is more compelling than “trust us, we’ll take care of you.”

Start with the 10-15 questions you answer most frequently, then build from there.

Document your onboarding process. Even if onboarding requires hands-on work, document the steps, milestones, and success criteria. This helps you deliver a consistent experience, train future team members, and identify where customers commonly stall.

Define success milestones. What does “getting to value” actually look like for your product? What should a customer accomplish by day 7? Day 30? Day 60? These milestones help you spot at-risk customers early and give you something concrete to drive toward during onboarding.

4. Establish feedback loops

Customer success sits at the intersection of customer and company. Part of your job is making sure insights flow in both directions.

Implement NPS or CSAT. Pick one to start. NPS gives you a pulse on overall loyalty and likelihood to refer; CSAT gives you feedback on specific interactions. Either way, you need a systematic way to measure how customers feel—not just anecdotes.

Create a product feedback process. How does customer feedback get back to the product team? Without a clear process, valuable insights die in support tickets. This can be as simple as a shared Slack channel, a monthly summary, or a tagging system in your support tool. The format matters less than having a consistent and reliable path from customer voice to product roadmap.

5. Set the rhythm

Finally, establish the operating cadence that will govern how you engage with customers.

Meeting cadences by tier. Based on your segmentation:

• Tier 1: Monthly check-ins, quarterly business reviews

• Tier 2: Quarterly check-ins, annual reviews if appropriate

• Tier 3: No standing meetings—outreach triggered by health score changes, renewals, or support escalations

Quarterly business reviews for top accounts. QBRs are your opportunity to step back from day-to-day support and talk about outcomes. What has the customer achieved? What’s coming up for their business? How can you help them get more value? These conversations strengthen relationships and surface expansion opportunities.

Internal reporting rhythm. Decide how you’ll report on CS metrics to leadership—weekly, monthly, or tied to board cycles. At minimum, track retention/churn, NPS, and support volume. Having a consistent reporting cadence forces you to keep your data clean and gives you a platform to advocate for resources as you grow.

Start simple, build and MVP, iterate from there

None of this requires expensive tooling or a large team. It’s about building the right foundations so you can retain customers, scale your efforts, and eventually grow the CS function as the company grows.

If you’re already using HubSpot for your CRM, I strongly recommend using HubSpot Service Hub for your CS foundation. Service Hub Pro does everything I described above: shared inbox, ticketing, knowledge base, customer feedback surveys, and basic reporting. It integrates natively with your existing customer data, which means no syncing headaches or duplicate records. And a 360 view of your customer in one shared system with sales & marketing is ideal.

Are there more sophisticated customer success platforms out there? Absolutely. But when you’re just getting started, you don’t need sophisticated—and you don’t need a sophisticated price tag.

The initial goal is to build foundational processes and understand your customers. You can always migrate to another CS platform later when your needs (and team) outgrow what Service Hub can do. For now, keep it simple and focus on execution, not tooling.

Get the MVP in place, then iterate.

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

Subscribe for weekly education, ideas, and frameworks

In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

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I’ve previously written about when to make other key GTM hires, so if you haven’t read those yet, they’re worth a look:

• When to hire an SDR

• When to hire your first AE

• When to hire a VP of Sales

• When to hire RevOps

Now let’s talk about customer success!

When to hire your first customer success manager

When should you hire your first CSM? It’s a question that doesn’t have a straightforward answer.

The advice you see most often is some version of “hire your first CSM when you hit $2M ARR” or “one CSM per $2M in revenue.” That’s not “wrong”, but it’s generic guidance that doesn’t account for the nuances that should actually drive this decision.

The truth is, some startups need a dedicated customer success hire after signing their third customer. Others can wait until they have 50. The difference comes down to four variables that determine how much post-sale effort your customers require—and who should be doing that work.

The four variables that determine timing

1. Who is your ICP?

Enterprise buyers expect white-glove service. They’re paying for outcomes, not just access to your software. When a VP is staking their reputation on your product working, they expect a dedicated point of contact who understands their business.

SMBs and startups have different expectations. They’re often more comfortable figuring (most) things out themselves—and in many cases, they actually prefer self-serve resources over scheduled calls.

2. What’s your average contract value?

At $200K+ ACV, losing a single customer is a significant revenue event. The math on a dedicated CS hire is straightforward: if one person can prevent even one enterprise churn per year, they’ve likely paid for themselves several times over.

At $5K ACV, you have more room to learn. You can tolerate some churn while you’re figuring out your onboarding process. The investment in a full-time CS hire needs to be justified by volume.

3. What’s the onboarding lift?

Some products require significant work before customers see value: integrations, data migrations, configuration, workflow setup. This isn’t optional—it has to happen, or the customer will never get to the “aha moment” that makes them want to renew.

Other products are ready to use out of the box. If your product falls into the first category, someone needs to own that onboarding work.

4. What’s the ongoing education and training requirement?

Some products tend to be more “set it and forget it.” Others require continuous engagement: training new users as teams grow, educating customers on new features or use cases, helping them evolve their usage. If your product falls into this category, the post-sale work doesn’t end after onboarding—it’s ongoing for the life of the customer relationship.

Putting it together: when to hire

High ACV + high-touch (enterprise, complex product)

If you’re selling $200K+ contracts to enterprise customers and the product requires significant onboarding, integration, or training, you need customer success early—likely after your first one to three customers.

Your founder and head of product can probably cover the first customer, maybe two.

But here’s the trade-off: most companies at this stage are still in a founder-led sales motion. Every hour your founder spends on post-sale work is an hour they’re not spending on finding and closing new deals.

You can make that trade-off consciously for customer one or two. But by customer three, you’re sacrificing growth. The profile for this hire is typically someone senior and consultative—possibly from a solutions engineering or professional services background.

Mid-market, moderate touch ($50-100K ACV)

You have more runway here. Consider hiring when you reach 5-10 customers, or when post-sale work starts consuming more than 30% of your founder’s time.

This person is likely a strong operations generalist who can handle onboarding, ongoing account management, and some light expansion conversations.

Low ACV + low-touch (SMB, quick onboarding)

If you’re selling to SMBs at lower ACVs and your product doesn’t require heavy onboarding, you can wait longer—often until you have 30-50 customers.

But waiting doesn’t mean doing nothing. Use this time to build self-serve infrastructure: a robust knowledge base, onboarding email sequences, in-app guidance. Hire when you start seeing churn patterns that indicate customers aren’t getting to value on their own.

The first CS hire in this context is more of a “Swiss Army knife”—support, onboarding, improving self-serve resources, and identifying patterns where customers get stuck.

A quick diagnostic

If you’re trying to figure out where you fall, ask yourself:

1. If we lost our biggest customer tomorrow, how much would it hurt?

2. How many hours per week is our founding team spending on post-sale work?

3. Are customers getting to value on their own, or do they need significant help?

4. Once customers are onboarded, do they need ongoing engagement or are they self-sufficient?

Your answers will tell you whether you’re in “hire now” territory or “build self-serve and wait” territory—and what kind of person you need when you do make the hire.

The type of person will also influence the cost to hire. The salary range for the roles I mentioned above could be anywhere from $75k-150k+/year depending on what level of seniority and sophistication you need.

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

Subscribe for weekly education, ideas, and frameworks

In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

Subscribe now

p.s. - Did you know I run another newsletter for fractional execs? If you know anyone who might benefit, send them to this link. I just published a highly requested article about how I navigated maternity leave last year.

The reality is - most sales stand-ups aren’t that effective.

And to be clear — weekly sales stand-ups are one of the most important meetings on your calendar. They should absolutely be happening. They’re how you keep your finger on the pulse of your pipeline, keep your team aligned, and catch problems before they become quarter-ending surprises. The issue isn’t whether to have them — it’s how you run them effectively and efficiently.

After working with nearly 30 startups, I can tell you that the most common format I see…going around the room and reviewing every single deal in the pipeline. And that just isn’t an effective use of your team’s time. Not every deal in your pipeline deserves weekly discussion.

Here’s the problem: deal-by-deal reviews don’t help you answer the questions that actually matter like:

1. Do we have enough new pipeline created to statistically hit our number?

2. Do we have enough pipeline coverage for the month/quarter to hit our number?

3. Where are deals stuck and how can we fix it?

4. And most importantly — if we’re off track, what are we going to do about it right now?

A good sales stand-up should take 30-45 minutes and accomplish three things: keep the team aligned on what’s happening across the business, give you a real-time read on pipeline health, and surface the deals that actually need group discussion. Everything else can be handled in your 1:1s.

This is the standing agenda I use across all of my client engagements. Feel free to steal it.

Key updates and team training (5-10 minutes)

This is your housekeeping block. Use it for anything the team needs to know before diving into pipeline — product updates, new feature releases, changes to pricing or packaging, competitive intel, or updates on strategic initiatives.

This is also a great time slot for brief team training. Maybe you want to do a quick roleplay on a common objection you’ve been hearing, share a new piece of sales enablement content, or walk through a recent win (or loss) and what the team can learn from it. Not every week needs training, but having a dedicated slot for it means it actually happens instead of getting perpetually deprioritized.

Keep this tight. If a topic needs more than 10 minutes, it gets its own meeting.

Pipeline review (20-25 minutes)

This is the heart of your stand-up, and it’s structured intentionally to move through the funnel from top to bottom. You’re not reviewing every deal — you’re reviewing the metrics and patterns that tell you whether you’re on track. And this section is supported by a dedicated pipeline dashboard.

Top of funnel

Net new opportunities

Start here because this is your leading indicator for revenue/quota attainment.

How many new deals were created this week? This month? And more importantly — are we on pace to hit our quota and revenue targets?

If you don’t know how many new deals you need to create, here’s the formula:

Net new deals needed = (revenue target ÷ average contract value) ÷ conversion rate

If you don’t have a reliable conversion rate yet (and honestly, most early-stage startups don’t), use 10% as a baseline. You can refine this over time as your deal stage tracking matures and gives you real data.

If you’re behind pace, this is where you talk about what to do now — not at the end of the quarter when it’s too late. Can we increase outbound activity? Is there a campaign we can accelerate? Are there partnerships we can tap?

The whole point of reviewing this weekly is to course-correct early.

Lead source analysis

Where are your new deals coming from? And does that source mix align with what you’d expect given your recent GTM investments?

For example, if you just sent three people to a conference last month, you should be seeing deals in the pipeline from that event. If you launched a new outbound campaign, are those leads converting? If referrals have dried up, why?

This isn’t about obsessing over attribution models. It’s about pattern recognition. You want to make sure your pipeline sources are diversified and that you’re getting a return on the time and money you’re spending to capture demand.

Middle of funnel

Pipeline coverage

Do you have 3-4x pipeline coverage for the current quarter? What about the upcoming quarter?

Pipeline coverage is the ratio of your total open pipeline value to your revenue target for a given period. For example, if you need to close $500K this quarter and you have $2M in pipeline, you have 4x coverage — meaning for every $1 you need to close, you have $4 in potential deals working.

This is the single most important metric for your forecasting confidence. If you need to close $500K this quarter and you only have $1M in pipeline, you’re undercovered and it’s time to take action. Either you need to create more pipeline, increase deal sizes, or accelerate timelines — and you need a plan for which lever you’re pulling.

I see a lot of startups skip this question entirely because they haven’t set up their deal stages properly and don’t trust their pipeline data. That’s a fixable problem, and it’s worth fixing fast — because flying blind on coverage is how you end up scrambling at the end of every quarter or year.

Bottom of funnel

Late-stage opportunities

Now you get into specific deals — but only the ones that are close to the finish line.

What’s in your final or late deal stages? What needs to happen to get these across the line? Are there blockers, risks, or stakeholders you haven’t engaged yet?

This is where team discussion actually adds value. Maybe your AE needs help navigating a procurement process, or your founder needs to make an executive-to-executive call to unstick a deal. Surface those needs here so the team can rally around them.

Large opportunities

Regardless of stage, any deal above a certain threshold (I typically use >$100-500K ACV, but adjust to what’s material for your business) gets a standing spot on the agenda.

These are your strategic deals — the ones that can make or break a quarter — and they deserve regular visibility even if they’re still early stage.

Conversion rates

This one comes with a caveat: you can only review stage-to-stage conversion rates once your deal tracking is consistent and you have enough data to make it meaningful. For many of the startups I work with, this is a “future state” item that gets added to the agenda once the foundation is solid.

But once you’re ready, this is incredibly powerful. Where are you losing the most deals? At what stage? Why? Is it a targeting problem (wrong ICP), a process problem (too slow, missing steps), or a people problem (skill gaps on the team)?

This is where sales becomes a science experiment — and you can only run that experiment if you’re changing one variable at a time and measuring the results.

A few rules to make this work

Prep before the meeting. You and your reps should update their pipeline before the stand-up, not during it. No one wants to sit through five minutes of someone fumbling through their CRM live. Set the expectation that pipeline data is current by the morning of your stand-up.

To make this easier, I always create a pipeline hygiene dashboard that flags deals with missing or stale data — things like a deal with no amount, no contact associated, or no activity logged in the last 10 days. That dashboard goes out to the team before the weekly meeting so reps know exactly what needs to be cleaned up. It takes the guesswork out of prep and means you’re walking into the stand-up with data you can actually trust.

Stay at the right altitude. Your top-of-funnel and mid-funnel review should stay at the metrics level — you’re looking at patterns and pace, not individual deals. But when you get to late-stage opportunities and large deals, that is the time to dig in. The whole point of those agenda items is to get specific about what needs to happen to close. The key is knowing when you’re in “metrics mode” versus “deal strategy mode” and not letting one bleed into the other.

Make it a habit. Same time, same day, same agenda, every week. Consistency compounds. You’ll start to develop an intuition for your pipeline rhythms, and your team will learn to self-diagnose issues before you even have to ask.

Track your leading indicators, not just lagging ones. Revenue closed is a lagging indicator — it tells you what already happened. Net new deals created, pipeline coverage, and deal velocity are leading indicators. They tell you what’s going to happen. Your stand-up should be focused on the leading indicators so you can actually influence the outcome.

Your weekly stand-up shouldn’t feel like a status report. It should feel like a working session where the team walks out knowing exactly where they stand, what’s at risk, and what they need to do this week to stay or get back on track.

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

Subscribe for weekly education, ideas, and frameworks

In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

Subscribe now

This week - we’re going to cover Sales Rules of Engagement (ROE). Enjoy!

Here’s a scenario I see play out pretty regularly: a startup hires its second or third sales rep, and within weeks, two reps are working the same account without knowing it. Or a deal closes and nobody can agree on who gets the commission. Or a sales advisor makes an intro through their personal email and the CRM has no record of it.

These aren’t edge cases. They’re inevitabilities if you don’t have a sales rules of engagement document in place.

A rules of engagement (ROE) document is one of those things that feels like unnecessary bureaucracy when you’re small…and then feels urgently overdue the moment something goes wrong.

The good news is that it doesn’t have to be complicated. The better news is — your team will be far more efficient with every ounce of clarity and structure you put in place.

When do you actually need rules of engagement?

My general guidance: if you have three or more account executives, it’s time to start drafting your ROE. If you have five or more sellers of any kind (full-time reps, part-time sellers, or sales advisors), you absolutely need one. No exceptions.

With just two reps, you can usually manage territory and deal ownership through informal conversations. But the moment you add a third person, informal agreements break down. People forget what was discussed, assumptions get made, and suddenly you’re mediating internal conflicts instead of closing deals.

The complexity increases exponentially with each new seller, especially when you start mixing full-time reps with part-time sellers and advisors who have different compensation structures.

What should your rules of engagement include?

Every startup’s ROE will look a little different, but there are core components every document should address. I’ve also created a free template you can download and customize for your team — grab it below.

Define your team structure and roles

Before you can establish rules, clearly define who plays what role. You might have full-time AEs who own deals end-to-end, part-time employees who sell alongside other responsibilities, sales advisors who make introductions but don’t manage the sales process, and channel partners who bring opportunities through their networks.

Each role has a different relationship to the deal, and your ROE needs to spell that out. For example, a sales advisor who makes a warm introduction should be credited as the referral source, but they shouldn’t be listed as the deal owner in your CRM if they aren’t responsible for the deal end-to-end. That distinction matters enormously for commission tracking and accountability.

Maintain a clear, up-to-date list of who is approved to own deals. If someone isn’t on that list, they can’t be a deal owner. Period.

Establish account ownership and territory rules

This is where most conflicts originate. Your ROE needs to answer: how are accounts assigned? How many can each rep own? What happens when a rep wants to work an account assigned to someone else?

Setting account caps (say 300-500) forces prioritization and ensures accounts are actually getting worked. You also need rules for account activity and retention — accounts with no meaningful engagement within three to six months should be subject to reassignment.

The goal isn’t to punish reps for long sales cycles; it’s to make sure named accounts receive the attention they deserve. If they aren’t after a defined timeframe — let someone else take a crack at it.

When a rep wants to pursue someone else’s account, give them a clear path: account trades by mutual agreement or collaborative selling with a commission split. Either way, document it.

Clarify deal ownership responsibilities

Deal ownership should mean end-to-end accountability, not just “I had the first meeting.” The deal owner is responsible for maintaining the deal record in your CRM with accurate stage progression, following your defined sales process including quotes and negotiations, managing all prospect communications, and maybe even following up on invoices for closed-won deals.

That last point surprises people, but it’s critical. The deal owner’s job isn’t done when the contract is signed — it’s done when cash is received. Extending ownership through collection ensures the rep stays invested in the customer relationship.

Set commission and split rules

Commission disputes are the fastest way to destroy trust on a sales team. Only approved deal owners should be eligible to receive commission, and the deal owner listed in your CRM at time of close is the commission-eligible party. Full stop.

For collaborative deals, keep it simple: limit splits to two reps maximum, use a standard 50/50 ratio, and require written documentation before the deal closes. For sales advisors, draw a clear line between referral compensation and sales commission — these are different structures that belong in separate agreements.

Address cross-sell and renewal ownership

These two areas cause the most confusion as teams grow, and they’re often left as “we’ll figure it out later.” Even if you don’t have the final answer, document the options you’re considering and set a timeline for deciding.

For renewals, there are two main approaches: the original deal owner retains the renewal (preserving relationship continuity) or the current sales territory owner or customer success rep takes it (simplifying accountability). All are defensible. The wrong answer is having no answer.

For cross-sells, decide whether reps must hand off to a different product specialist, can own it themselves with specialist support, or some hybrid. Whatever you choose, make sure the referring rep gets recognized through a referral bonus or split commission.

Define leadership involvement thresholds

Your ROE should define at what deal size leadership needs to be involved. A simple framework: for deals under a certain ACV threshold (maybe $100K), reps have full autonomy. For deals above that threshold, reps invite leadership to key conversations. Leadership can always decline, but they should have visibility.

This builds rep confidence while ensuring your highest-value opportunities get executive attention.

Require CRM hygiene and communication standards

Your rules are only as good as your CRM data. Require that all sales communications use company email addresses that are automatically logged, every deal is opened in the CRM with accurate stage progression, and regular audits are conducted to ensure compliance. This ties directly into the RevOps foundation I’ve written about before.

A few final thoughts

Your ROE doesn’t have to be perfect on day one. It’s a living document that will evolve as your team grows. Mark sections as “draft” when you’re still working through the best approach — it’s better to acknowledge a decision is in progress than to leave a gap entirely.

I’d also recommend involving your sales team in creating the ROE. The people doing the selling will surface scenarios you haven’t considered, and when reps participate in building the rules, they’re far more likely to follow them.

If you’re in the process of building your sales team and haven’t created a rules of engagement document yet, start now. Don’t wait for the first conflict — by then, the damage to trust and team cohesion is already done.

👉 Download my free Sales Rules of Engagement template to get started.

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

Subscribe for weekly education, ideas, and frameworks

In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

Subscribe now

Thanks for reading GTM for Startups by Jess! This post is public so feel free to share it.

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In Part I, we covered what GTM strategy actually means, the four sources of revenue, and three principles for building a strong strategy. I also shared some examples from my client work that illustrate why you can’t just copy someone else’s playbook.

This week, we’re getting into the how — a practical framework for evaluating which GTM tactics actually deserve your time, money, and energy based on your specific situation.

A quick caveat before we dive in: this is one of the hardest topics to give general advice on. But I’m gonna try anyway because — I like hard things.

Which tactics will work for you is incredibly specific to your company — your ICP, your buyer personas, your competitive landscape, your budget, your stage.

What I’m sharing here is my best effort at a general framework based on patterns I’ve seen across 30+ startups (and troves of data that I’ve read on the topic over the years). But take everything with a grain of salt and always filter it through the lens of your own unique situation.

Two categories of GTM investment

At the highest level, I think about GTM tactical investments in two categories:

1. The non-negotiables — tactics that almost every company should invest in regardless of who you’re selling to or how early you are

2. Everything else — the tactics that vary based on your ICP, stage, and resources

The first category is straightforward. The second is where the real strategic decisions live — and where most founders either spread themselves too thin or pick the wrong things.

Let’s break each one down.

The non-negotiables

Organic growth

Your existing customers are your lowest-hanging fruit. They already know you, trust you, and have presumably seen value in your solution. That makes them your lowest-effort, highest-quality source of pipeline.

Organic growth should always be top of mind. That means requesting referrals from your customers, incentivizing them to make those referrals, providing a kickass customer experience, and making sure you’re on top of renewals and upsells.

This isn’t a “nice to have” — it should be a staple of every GTM strategy.

Your current customers should also become part of your marketing strategy. Their faces and voices are your best marketing.

I’ve written about the full-funnel power of customer reviews and case studies, if you want to go deeper there. I also plan to cover customer success tactics in greater detail this year — so stay tuned.

Your website

Your website is your only 24/7 salesperson.

Every single GTM tactic you deploy is eventually going to lead people back to it. Paid search leads people to your website. PR leads people to your website. Cold outreach — when someone gets a cold email that piques their interest, the first thing they do is go check out your website.

Hell, even REFERRALS lead people to your website. When someone makes a recommendation to me in passing/verbally, the very next thing I do before I opt into that referral is…check out their website.

That’s why investing in your website is non-negotiable for everyone.

It doesn’t matter what stage you’re at, who your ICP is, or what your budget looks like. If your website doesn’t clearly communicate who you are, what you do, for who, and why someone should care, every other tactic you invest in will underperform.

Founder brand

There’s significant research that suggests consumers and businesses alike are much more likely to purchase a product or service if the CEO, founder, or executive team is active in the market and people feel like they know that person. It’s the humanizing factor, and it drives results.

This applies across the board — B2C, B2B, startups, even enterprises. Nine times out of ten, elevating your personal brand is a tactic that should be in your GTM strategy.

You can build your founder or executive brand through social media (more on that below) and through PR — think guest podcast appearances, securing speaking opportunities, or panel spots at conferences. It doesn’t require a big budget. It requires consistency and a willingness to put yourself out there.

Funny…I’d been giving this advice for years before I realized someone wrote a whole book on it, too —> check out Founder Brand if you still aren’t convinced.

Everything else…how to identify which other tactics to invest in

This is where it gets interesting — and where most generic GTM advice falls apart.

Start with your ICP and buyer persona

Before you evaluate any of the tactics below, you need to know who you’re trying to reach. This is exactly why defining your ICP and buyer personas is so critical. You can’t confidently determine which channels and tactics will work until you deeply understand who your target audience is, where they spend their time, and how they make purchasing decisions.

If you haven’t done that work yet, go back and do it first. Everything below depends on it.

Talk to your customers (and your team)

The single most effective way to figure out which tactics will work for your business is to talk to your customers and prospective customers. Ask them directly things like:

• How do you find out about new products or solutions?

• Who do you turn to for advice and recommendations?

• Where do you consume industry information?

• When you were evaluating us, what did that process look like?

Additionally, consider conducting a customer journey mapping exercise with your entire customer-facing team. There are people across your organization — sales, customer success, marketing, even product — who have institutional knowledge about how your prospective customers discover and vet new solutions.

A structured exercise to surface all of that knowledge will pay off tenfold and help you avoid investing in tactics that don’t match how your buyers actually behave.

Pick 3-5, not all of them

Here’s the critical part: as a startup, you should only pick 3-5 of these tactics to invest the majority of your time and energy in. Any more than that and you’re going to spread yourself too thin.

As you evaluate all of the options below, disqualify first, and then stack rank which ones you think will drive the most impact for your business and invest in your top choices. Master those before expanding.

As you grow and have more resources — more people, more budget — you can layer in additional tactics. Enterprise-level companies like Salesforce and HubSpot do all of these things now. But they didn’t start that way, and you shouldn’t either.

Evaluating your options

With your ICP defined and your customer research in hand, here’s how to think about each major tactic. The easiest approach is often to disqualify tactics first to narrow down your options. Then stack rank what’s left.

Paid search

Paid search is generally a viable tactic if one or more of these three things are true: your average contract value is relatively small (think sub-$1,000), there’s actual search volume for your keywords, or you can a very specific buyer persona through paid social.

Note: Paid ad targeting options vary drastically for search engines vs social and even across social platforms.

Why the ACV threshold? People don’t spend a ton of time deliberating on purchases under $1,000. They search, they find you, they buy — the decision cycle is short, and paid search may pay off pretty quickly.

But the more expensive your product is, the less likely someone is going to just buy it with a credit card after clicking an ad. It’s going to go through a more rigorous sales process, which means paid search alone is less likely to generate immediate returns.

That’s a broad strokes way of thinking about it — it’s more nuanced than just this. I’ve published an entire series on paid ads with my friend Peter Guba that goes much deeper: when to introduce paid ads, how to determine the best channels, and how to develop your budget.

Content marketing and SEO

Whether content marketing and SEO make sense for you really depends on how your particular prospect evaluates their options.

In Part I, I shared the example of a client selling FX and treasury infrastructure to financial services companies. There was virtually no search volume for their keywords. Their prospective customers turned to peers and trusted advisors for referrals — they didn’t go to Google. SEO was never going to be their fast path to growth.

This is where those customer interviews I mentioned earlier are going to pay off. If your customers tell you they turn to Google when evaluating new solutions, and you can confirm that search volume actually exists for your keywords, then SEO may be a strong strategy for you.

To validate this, you can use third-party tools like Semrush to check keyword volume and to look at where your competitors are getting their traffic from — whether that’s organic search (SEO), AI-generated search (AEO), or paid ads. That data is accessible to the public (some behind paywalls, some free), though you may want to work with a marketing expert to interpret it. It can be hard for someone who’s not a marketer to just jump into Semrush and dissect the data.

If you know you have one or two bigger competitors that are pretty active online, Semrush or a similar tool will help you understand how they’re getting their traffic. That competitive intelligence alone can help you decide whether SEO is worth your investment.

One important caveat: you may still create content even if SEO isn’t part of your core strategy. Content serves purposes beyond search rankings — it can be used for sales enablement, nurturing prospects, supporting customer onboarding, and more. SEO is not the only reason to create content.

I’ve written more about this in my sales enablement article.

Social media

Organic social media is generally a great tactic for almost any company. It’s a relatively inexpensive way to build your brand and distribute your marketing content.

The platform you choose is going to depend on your ICP. Different platforms have different demographics, so depending on whether you’re selling primarily to women or men, consumer products or B2B, you might choose Instagram over LinkedIn, or vice versa. The specific platform may vary, but almost always, a social media presence is a solid tactic and a distribution channel for all of your other marketing efforts.

PR

PR is another tactic that’s great for most companies. The key is to start scrappy. There are low-cost PR tactics that can move the needle without a big investment — things like pitching yourself for podcast appearances, writing guest articles, or leveraging your own network for introductions to journalists.

Once you have more capital and a bigger budget, it’s almost always true that investing further in PR will help elevate your brand. But you don’t need to wait until you can afford a $10k/month agency to get started. I’ve put together a PR starter kit for startups with a practical, low-cost way to get going.

Conferences and events

Some form of conferences and events should be incorporated into almost every GTM strategy. But you want to be highly selective about which ones you attend to maximize your ROI. And by ROI — I’m not just referring to the financial cost — I’m also referring to your most sacred commodity — your time.

I would prioritize conferences where you can secure a speaking opportunity, host a roundtable, or an intimate dinner — something where you can connect with your buyers one-to-one. This is very different from just showing up and walking around a convention center with a thousand other people, or paying for a booth.

Paying for a booth is almost never the most economical way for a startup to build pipeline. But attending the right niche conferences? That can make a huge difference. In Part I, I gave the example of the company selling software to veterinarians that generated 90% of their pipeline from niche veterinary conferences. For some ICPs, conferences are a massive part of the strategy.

Your customer interviews and journey mapping exercise will help you determine how much of your strategy should hinge on conferences and which ones are worth your time.

You can also host your own events — executive dinners, roundtables, happy hours. Self-hosted events are almost always high ROI because you control the audience that’s invited, the conversation, and the budget. I highly recommend almost every company invest in hosting their own events. I’ve written more about this in my IRL events guide.

Cold outbound

As I covered in Part I, cold outbound is the lowest-converting channel overall and tends to produce the lowest-quality leads. But it may be more or less effective for you based on who you’re reaching out to and the price of your product.

If you’re selling a less expensive, more commoditized product, you may have decent success with cold outreach and conversions. But the more expensive your product is, the less likely that cold outreach will be highly effective. If you’re reaching out cold to enterprises about a six-figure deal, the odds are not in your favor.

Certain personas also tend to be more receptive to cold outbound than others. Studies have found that HR, sales, and marketing buyers are more likely to respond to cold outreach than technical buyers like CTOs or heads of data science. If your buyer persona is in one of those more receptive categories, outbound might have a role in your strategy. If you’re selling to deeply technical buyers, temper your expectations.

For more on outbound tactics, check out The LinkedIn Outbound Advantage.

Partnerships and ecosystems

Partnerships and ecosystem development are also almost always good tactics, but in some cases, they’re essential to your GTM strategy.

For certain enterprise products, the buyer may always use a consultant to verify the purchase. If that’s the case, then partnering with Big Four consulting firms or other influential advisors in your space isn’t just “nice to have” — it’s critical, because those firms are always going to be involved in the buying decision.

How central partnerships need to be in your strategy really varies company to company. It comes down to understanding your buyer’s decision-making process: who else is involved in the purchase? If the answer is “consultants, advisors, or complementary vendors are always in the room,” then partnerships need to be a top priority.

I’ve written a whole series on this topic, starting with Nearbound 101: Types of B2B Partnerships.

Account-based marketing (ABM)

If you’re selling into enterprises, account-based marketing is almost always a good idea. ABM flips the traditional marketing funnel — instead of casting a wide net, you identify specific high-value accounts and tailor your outreach and marketing efforts directly to them.

For enterprise-level sales where deal sizes are large and buying committees are complex, ABM helps you focus your limited resources on the accounts that matter most. My good friend Corrina Owens has written a deeper dive on this in ABM 101.

Putting it all together

Here’s the short version:

Do these no matter what: Invest in organic growth, your website, and your founder brand. These are your non-negotiables.

Then choose 3-5 additional tactics based on your ICP, your customer research, and your stage. Stack rank them by expected impact and go deep on your top choices.

Don’t try to do everything at once. Salesforce and HubSpot do all of these things. You’re not Salesforce and HubSpot — yet. Master a few tactics first, then expand as you grow.

And remember — the best way to know what will work for your business is to actually ask your customers and prospects. The frameworks and guidance above can help you narrow things down, but nothing replaces firsthand insight into how your buyers discover, evaluate, and purchase solutions like yours.

See ya next week.

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

Subscribe for weekly education, ideas, and frameworks

In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

Subscribe now

Go-to-market success really comes down to two things: your strategy AND your execution.

“GTM strategy” is one of those terms that gets thrown around constantly but means different things to different people. Some think it’s just about picking marketing channels. Others conflate it with a product launch plan.

I’ll share how I define and approach it tactically.

What GTM strategy actually means

To develop your go-to-market strategy, you need to answer two foundational questions first:

1. Who are we targeting? This means defining your ICP (ideal customer profile) and buyer personas with specificity.

2. How are we positioning ourselves as unique and differentiated to that audience?

Only after you’ve confirmed those two things do you move on to the tactical question:

What channels and tactics make the most sense to engage and convert that audience?

Getting this order wrong is one of the most common mistakes I see founders make.

They jump straight to “should we try LinkedIn ads?” before they’ve nailed down who they’re actually trying to reach and why those people should care.

The four sources of revenue

Here’s the thing—at the highest level—there are really only four sources of revenue for any company:

1. Inbound – Interest generated as a result of marketing efforts

2. Outbound – Interest generated through proactive sales efforts

3. Nearbound/Channel – Pipeline from partnerships and ecosystem relationships

4. Organic/Existing Customers – Renewals, upsells, and referrals

That’s it. Every tactic you’ll ever use falls into one of these four buckets.

And within each bucket, there’s a finite set of tactics available to you:

Three principles for building a strong GTM strategy

1. Diversify your efforts

Don’t invest solely in one source or tactic.

There are always variables changing outside your control—LinkedIn’s algorithm changes, Google updates its search ranking, a key partnership falls through, conference attendance drops.

Also consider the lead quality by source.

Not all pipeline is created equal in terms of effort or quality:

• Existing customers are your lowest-hanging fruit (lowest effort, highest quality). They already know you, trust you, and have presumably seen value in your solution.

• For net-new logos:

  • Inbound leads are the highest quality, but they take the most time and effort to develop.

  • Partnership and channel leads are your second-best quality source—they come with built-in trust from the referral.

  • Outbound motions are the easiest to get going…but also the lowest quality. Warm outbound motions using triggers like recent news or technographics performs better than pure cold, but as a category it’s still the lowest conversion (~1%) and quality—relatively speaking.

The smart play? Invest in a mix of short-term, faster tactics while building the groundwork for higher-quality, longer-term sustainability.

2. Pick 3-5 tactics to focus 80-90% of your time and energy on

Don’t spread yourself too thin. Early-stage companies have limited resources—time, budget, people. Trying to do everything means doing nothing well.

Choose 3-5 tactics where you can genuinely invest the majority of your time and energy. Master those before expanding.

This is a great relatively recent resource that details what is working best right now for various ACVs, maturities, etc.

Note: This is generalized data for B2B software—not industry or ICP specific.

Article: What's working in GTM right now

3. Consider what will actually work for your ICP

This is where most generic GTM advice falls apart. What works for your target audience depends entirely on who they are:

• Where do they consume information?

• Who do they trust?

• Where do they “hang out”?

• When and where are they most engaged to absorb new information?

The answers can vary dramatically by audience.

Why “best practices” don’t always apply

Let me share a few examples from my client work that illustrate why you can’t just copy anyone else’s GTM playbook without fine-tuning it for your specific fact set:

• Technical buyers don’t respond well to cold outbound. CTOs, heads of data science, and engineering leaders are statistically the least likely to respond to cold outreach. Sales, marketing, and HR buyers are the most responsive (relatively speaking). But even then—remember, cold outbound averages around a 1% conversion rate.

• Some audiences aren’t on traditional digital channels. I worked with a company selling software to veterinarians. They generated 90% of their pipeline from niche veterinary conferences. Why? Vets spend their days with animals—not scrolling LinkedIn or searching Google. But when they attend industry conferences, they’re highly engaged and actively looking for solutions.

• Some markets have no search volume. I worked with a company selling FX and treasury infrastructure to financial services companies. There was virtually no Google search volume for their keywords. SEO wasn’t going to be their path to growth. This audience is most likely to turn to their peers or trusted advisors for referrals.

• New categories face a search volume challenge. I’ve worked with several companies creating first-of-their-kind solutions aka creating new categories. Keyword search can be challenging when no one is searching for your category yet. People search for “CRM for startups” or “HubSpot alternatives” because they know CRMs exist. If you’re creating something entirely new, the SEO playbook may not work.

So how do you figure out which tactics are right for you?

That’s exactly what I’ll cover next week—a framework for evaluating which GTM tactics deserve your investment based on your specific ICP, stage, and resources.

See ya there.

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

Subscribe for weekly education, ideas, and frameworks

In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

Thanks for reading GTM for Startups by Jess! This post is public so feel free to share it.

Share

I recently migrated my newsletter from beehiiv to Substack and this is the first edition from the new platform! If you find any hiccups…let me know, please! It was a process to migrate (sigh). But I did it.

If you’ve been following along, you know I talk a lot about preparing for your first sales hire and how to transition out of founder-led sales. Another asset that you need to create to make the transition and scale your team is a sales playbook.

And I haven’t (yet) broken that asset down in detail—what it is, why you need one, and exactly what goes in it.

This week, let’s fix that!

Why you need one

A sales playbook is the single source of truth for how your company sells.

It’s where your sales process, messaging, objection handling, and competitive intel all live—documented and accessible to every sales rep—current and future.

Here’s why this matters for early-stage startups:

• It’s how you transition out of founder-led sales. No one will ever sell the way you do. You have context, conviction, and credibility that can’t be replicated. But when it’s time to hire your first rep, you need to extract everything that works from your head and document it. What questions do you ask on discovery calls? How do you handle the pricing objection? What stories do you tell to build urgency? A playbook codifies what you do instinctively so as much as possible becomes repeatable for the people you hire.

• It accelerates onboarding. Remember that six-week onboarding roadmap I shared? A playbook is where those resources live. Instead of answering the same questions repeatedly or having new reps shadow you for weeks, you point them to the playbook.

• It creates consistency. As you add reps, a playbook ensures everyone is telling the same story, qualifying the same way, and handling objections with messaging that’s been tested and refined.

• It turns sales into a measurable system. Sales is a never-ending science experiment. The problem is, if you change five variables on every deal, you have no idea which variable impacted the outcome.

• It forces clarity. The act of documenting your sales process often reveals gaps you didn’t know existed. You’ll discover you’ve never actually written down your ICP criteria, or that your “discovery process” is really just winging it.

The more you can standardize your process—supported by documentation—the more you can control the variables. And when you control the variables, you can actually measure what’s working and pinpoint where things break down.

This becomes essential as you build your team. When a deal is lost or a rep is underperforming, you need to be able to diagnose whether it’s a person problem, a process problem, or a product problem. Without a documented, standardized approach, everything looks like a person problem—and that’s not fair to your reps or useful for improving your business.

Where to store it

Your playbook needs to live somewhere your team will actually use it. I recommend Confluence (an Atlassian product) or Notion—both offer very generous startup discounts that make them accessible at your stage.

If I had to pick one, I’d go with Confluence. Why? They have a deeper integration with HubSpot, where you can access Confluence directly from HubSpot’s AI chat. That means your reps can pull playbook content without leaving their CRM—reducing friction and increasing the odds they’ll actually reference it in the moment.

Notion is a solid alternative if your team already lives there, but the HubSpot integration gives Confluence an edge for sales-specific use cases.

“Why can’t we just use a Google doc?”

If you must…it’s better than nothing. But it’s much easier to navigate, search, and see when a specific section was last updated etc. in one of the platforms I mentioned.

What to include in your playbook

Building a playbook can feel daunting, so I’ll break it into two phases. Phase 1 is your minimum viable playbook. Phase 2 is what you add once the MVP foundation is in place.

Phase 1: The minimum viable playbook

These are the non-negotiables. Get these documented before day one of your new hire’s onboarding if possible or as soon as possible thereafter:

• Mission, vision, and values. Set the foundation for how you operate as a company and how you want your reps to represent your brand in the world.

• Founder & company origin story. Include a link to a recording of you telling the story—why you started the company and where you see it going. This gives reps the narrative they need to sell with conviction.

• Product overview. Cover your product(s), key features, the pain points they solve, and who the buyers are for each.

• Pricing. Detail how you price the product so reps aren’t stumbling over their words on sales calls.

• ICP and buyer personas. Go deep here. If you haven’t already, use these frameworks on how to define your ICP and how to refine your buyer personas to get this right. Include real examples of current customers and real people who have bought from you before. Link to a full customer list if possible so reps can study the names and start recognizing patterns.

• Competitors. Document who you’re up against, including the status quo of “do nothing”. Explain how you’re different from each.

• Positioning. How do you position the product to different ICPs and buyer personas? Sometimes you highlight different value drivers to a CFO than you would to an HR manager—you’re selling the same thing but emphasizing what matters to each. Same goes for industry differences (financial services vs. professional services, for example).

• Sales process and deal stages. Map out exactly how a deal moves from first touch to closed-won.

• Sales tech breakdown. List every tool in your stack, what license types you have, why you use it, how you use it, and who the admin is for granting access.

• Glossary. Define any acronyms, company-specific terms, or industry jargon a new rep might not know.

• On-demand demo recording. A video they can watch repeatedly to learn the product and your demo style.

• Recent sales call recordings. Include at least three so reps can hear how you actually sell.

• Links to key sales assets. One-pagers, decks, proposal templates—everything they’ll need, in one place. (This is sales enablement 101.)

  • Case studies and social proof. If available, include case studies, customer reviews, or NPS survey results.

Phase 2: Level up your playbook

Once phase 1 is solid, start layering in these elements to make your playbook more comprehensive:

• Standard company and product overviews. Two to three sentence blurbs people can use to explain the company or product consistently in emails, on calls, or at events.

• Messaging document. Teach reps exactly how you want them to talk about the problems you solve, the product, and the company—consistently.

• Written sales pitch script. I love April Dunford’s framework for structuring a compelling pitch.

• Discovery questions. A list of the key questions reps should ask to qualify and understand prospects.

• Qualification framework. Detailed guidance on how to qualify a prospect and when to disqualify.

• Objection handling. Document common objections and exactly how to address them.

• Prospecting playbook. What tools should reps use? What signals should they look for—M&A activity, recent funding, layoffs, leadership changes? (And don’t sleep on LinkedIn as an outbound channel.)

• Demo best practices. More detailed instructions on how to give a great product demo beyond just watching your recording.

• Product deep dive. Cover integrations, implementation process and timeline, security and compliance details—anything reps will get asked about during the sales process. Make it fast for them to find answers.

• Email templates. Standardize as much as possible through templates for cold outreach, post-discovery follow-up, post-demo recap, pricing delivery, and any other frequent touchpoints.

• Internal process SOPs. Detailed documentation on how to do all of your internal sales processes—updating the CRM, submitting contracts, requesting discounts, etc.

This isn’t a “nice to have” - it’s essential for success

A sales playbook isn’t a nice-to-have—it’s how you scale beyond the founder. If everything that works about your sales process lives in your head, you’re the bottleneck. And every new rep you hire will take longer to ramp, make more mistakes, and require more of your time.

It’s also really hard to hold people accountable to following a process or hitting their quota…if you don’t have the process written down anywhere (or the information is scattered across dozens of Slack threads and documents).

Start with phase 1. Get the minimum viable playbook done—ideally before your first hire starts. Then iterate and expand as you learn what else your team needs to feel confident and close.

Related content: Check out this pre-hire checklist and sales onboarding roadmap. These three pieces together will 5-10x your odds of a successful first sales hire.

Bonus: Here is a template you can use to collate and organize this information.

Sales Playbook Template

Questions? Shoot them over. You’ve got this! 🫡

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

Subscribe for weekly education, ideas, and frameworks

In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

Subscribe now

Thanks for reading GTM for Startups by Jess! This post is public so feel free to share it.

Share

A founder makes their first sales hire, offers a competitive base salary, maybe throws in a commission percentage, and calls it a day. No quota. No clear OTE. No math connecting all the pieces.

Then six months later, everyone’s frustrated.

The rep isn’t making the money they expected. The founder doesn’t know if performance is good or bad. And both sides are left wondering what went wrong.

The answer is almost always that the comp plan was broken from the start.

The good news is - I’ve got a guide for you to follow to fix it. 👇

A founder’s guide to building a sales comp plan

The building blocks of sales compensation

Sales compensation isn’t just about paying someone fairly - it’s a mathematical system that aligns expectations and incentives between you and your rep. When the math doesn’t work, both sides end up unhappy.

Let me give you the four components every sales comp plan needs:

• Base salary is the guaranteed portion. This is what your rep earns regardless of performance.

• Variable compensation (based on commission) is what they earn when they hit quota. This is where the money motivation kicks in.

• Commission rate is the percentage of each closed deal the rep earns. If quota is $500K and variable comp is $50K, the commission rate is 10%.

• Quota is the revenue target that determines when they’ve “earned” their full variable comp.

• Together, base plus variable equals OTE (On-Target Earnings) - what the rep makes when they hit 100% of quota.

Here’s the problem: I regularly see founders offer a base salary and a commission percentage without ever setting a quota. Or they set all three, but the numbers don’t reconcile. A rep can’t back into what they’ll actually earn, and the founder can’t define what “good” looks like.

This isn’t just a founder problem, though…

A red flag during hiring

If you’re interviewing a sales candidate and they accept your offer without asking detailed questions about quota, OTE, ACV, and how commission is calculated - that should concern you.

Salespeople are money-motivated by design. That’s the whole point. A strong candidate will immediately do the math: “If my base is $70K and my OTE is $130K, that means I need to earn $60K in variable. What’s my quota? What’s my commission rate? How many deals do I need to close to hit that number?”

If they’re not asking these questions, one of two things is happening: Either they don’t understand how sales comp works (which means they’re inexperienced), or they’re not actually motivated by the money (which means they might not have the hunger you need).

A good sales hire will pressure-test your numbers before accepting. They’ll want to know:

• Is this quota realistic given the sales cycle?

• How many deals does that require at our average contract value?

• What’s the current close rate on opportunities?

• Is there pipeline or lead gen support to hit those numbers?

This is exactly the conversation you want to have. It forces you to think through the math together, and it shows you that this candidate will hold themselves accountable to clear targets.

⚠ Bottom line: Pay attention to the questions the candidate is asking you! It’s a signal.

The startup guide to building a sales comp plan

Now let’s walk through how to actually build a comp plan that works. I’m going to use general market benchmarks from RepVue and a framework that’s realistic for early-stage companies.

If you are looking for more specific benchmarks based on your revenue, valuation, etc - I’d recommend using Pave.

Step 1: Determine market-rate OTE for your segment

Before you attempt to structure a comp plan, anchor yourself on the current market benchmarks. OTE varies significantly based on whether you’re selling to small businesses, mid-market companies, or enterprises.

According to RepVue’s 2025 data:

• SMB Account Executive: $70K median base / $130K median OTE

• Mid-Market Account Executive: $90K median base / $172K median OTE

• Enterprise Account Executive: $135K median base / $260K median OTE

These are medians - so of course some companies pay above, some below. But if your OTE is significantly under market, you’ll struggle to attract strong candidates. If it’s significantly over, you might struggle to hold them to a quota that makes it an attractive ROI for you as the employer.

Step 2: Structure the base/variable split

The industry standard is a 50/50 split between base salary and variable compensation. This means if you’re offering $130K OTE for an SMB AE role, you’d structure it as $65K base and $65K variable (earned at quota).

Some companies run closer to 60/40 (more base, less variable) or 40/60 (less base, more variable). A higher base feels safer for candidates but reduces the performance incentive. A lower base may be a hard sell for your startup, the candidates already know they are taking a ‘risk’ trying to sell for an early stage company - lower guaranteed pay may make that risk too high.

For most startups, 50/50 is the sweet spot. It’s what candidates expect, and it creates meaningful upside for performance.

Step 3: Set a realistic quota

This is where most founders go wrong. They either don’t set a quota at all, or they pick a number that sounds good without testing whether it’s achievable.

The startup-friendly approach: Set quota at 3-4X the base salary.

Using our SMB example with a $65K base, that means quota would be $195K-$260K in annual closed revenue.

This approach results in commission rates around 25-33%, which feels generous and attracts candidates. It also creates achievable targets for early-stage companies still building their sales infrastructure.

The enterprise approach: Mature companies typically set quota at 4-5X OTE (not base).

According to SaaStr’s analysis of sales compensation data, this 4-5X ratio “remains the standard,” with enterprise quotas often pushing to 5X or higher. QuotaPath’s research confirms that “a quota with a multiplier of 5x the OTE is what we’ve observed as the SaaS standard.” Using our $130K OTE example, that translates to $520K-$650K in quota, with commission rates around 10-12%.

This approach works when you have documented close rates, proven messaging, consistent lead flow, and existing reps hitting quota. It doesn’t work when you’re still figuring out product-market fit or in the early stages of founder-led sales transitions.

Why do I recommend the startup-friendly approach?

Because unrealistic quotas kill motivation and drive turnover. RepVue data shows quota attainment rates ranging from 24% to 52% depending on the company - meaning at many organizations, fewer than half of reps hit their number. Setting achievable quotas keeps your reps motivated while you build the systems to support higher productivity over time.

ℹ Note: You can and should restructure sales comp plans as your company and sales process matures.

Step 4: Validate the quota with deal math

A quota number is meaningless if the underlying math doesn’t work. Before finalizing it, pressure-test it against your ACV and required deal velocity.

The formula: Quota ÷ Average Contract Value = Deals Required

Let’s say you set a $240K quota and your ACV is $20K. That’s 12 deals per year, or one deal per month. That feels achievable.

But if your ACV is $8K, that same quota requires 30 deals - 2.5 per month. With a 90-day sales cycle, can one rep manage that many concurrent opportunities?

Now factor in close rates. If you close 20% of qualified opportunities, you need 60 opportunities to get 12 deals. That’s 5 new qualified opportunities per month, every month. Is your marketing engine producing that volume? Or do you think the rep can realistically create that many net new opportunities on their own, while also working open deals?

Step 5: Calculate commission rates

Once you’ve set a validated quota, work backwards to determine the commission percentage.

The formula: Variable Compensation ÷ Quota = Commission Rate

Examples using a $65K variable target:

• $195K quota (3X base) = ~33% commission rate

• $227K quota (3.5X base) = ~29% commission rate

• $260K quota (4X base) = 25% commission rate

You can structure this as a flat rate (same percentage on every dollar) or tiered/accelerated (higher percentages after hitting certain thresholds).

Accelerators reward over-performance and make top performers very happy, but budget carefully - a rep at 150% of quota with accelerators can get expensive fast. However - the expense may be 100% worth it if you’re in logo acquisition mode and not yet as focused on unit economics.

Step 6: Build in ramp period compensation

Here’s another reality founders often miss: Even with perfect onboarding, a new rep won’t close deals immediately. If your sales cycle is 90 days and you need a month of training, you’re looking at 4+ months before the first commission check.

Ramp time = Onboarding period + Sales cycle length

Paying only on closed deals during this period creates financial stress and turnover risk. Instead, structure activity-based bonuses for the first 90 days that reward the behaviors leading to future closes:

• $200-500 per qualified meeting booked

• $500-1,000 per qualified opportunity created

• Monthly bonus for hitting activity targets (e.g., $3K for 8 qualified meetings)

This keeps your rep financially stable while building pipeline, and gives you leading indicators of whether the hire is working out before you’ve invested 6+ months.

Why early wins matter for retention

There’s another reason to think carefully about ramp period structure: early wins predict whether a rep will stick around.

The logic chain is straightforward. When a new rep closes their first deal, it validates their decision to join your company. It builds confidence that they can succeed in your environment with your product. That confidence translates to engagement, and engaged employees are far less likely to leave.

The inverse is equally true. A rep who goes months without closing anything starts to doubt themselves, doubt the product, and doubt whether they made the right choice. That doubt compounds quickly - and before you know it, they’re interviewing elsewhere.

This is why some sales leaders intentionally set up new hires for early wins. They might assign a “softball” opportunity that’s likely to close, or let the new rep shadow a deal that’s already in late stages so they can share in the commission and the victory. The goal isn’t to inflate their numbers artificially - it’s to give them the confidence boost that comes from proving they can sell here.

When you’re designing your ramp period, think about how you can engineer opportunities for early success. The faster a rep experiences a win, the more likely they are to stay long enough to become a consistent performer.

Step 7: Define activity standards for ongoing management

You don’t want to wait until quarter-end to know if your rep is on track. Establish weekly and monthly activity targets based on your quota math.

Using our 12-deal quota example with a 20% close rate: The rep needs 60 opportunities annually, which is 5 per month or roughly 1-2 per week. That’s your leading indicator.

If a rep consistently misses activity targets after ramp, you have early signal that something’s wrong - whether it’s the process, the market, or the individual’s performance.

Put it in writing

Every element of this plan should be documented in your offer letter or compensation agreement:

• OTE and base/variable split

• Quota amount and how it was calculated

• Commission rate and structure (flat, tiered, or accelerated)

• Ramp period terms and activity bonuses

• Payment timing (monthly, quarterly, upon payment receipt)

• Any clawback provisions

If your rep can’t look at the document and calculate exactly what they’ll earn at different performance levels, you need to simplify it.

The math needs to math for everyone

Sales compensation is a system, and every piece needs to connect. A base salary alone isn’t a comp plan. A commission percentage without a quota is meaningless. OTE without validated deal math is a fantasy.

Get this right from the start, and you set both yourself and your rep up for success. Get it wrong, and you’ll spend months wondering why things aren’t working - when the answer was baked into the numbers from day one.

Related articles

• Preparing for your first sales hire: A checklist for Founders

• Sales hiring: Expectation management & leading indicators of success

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

Subscribe for weekly education, ideas, and frameworks

In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

Thanks for reading GTM for Startups by Jess! This post is public so feel free to share it.

Share

So next up - marketing!

Let me know what you think. Truly. 🙏

How to ramp up as your startup’s first marketer

If you’re reading this, you either just hired your first marketing person or you just got hired as that first marketing person at a startup. Either way, congrats! 🎉

A note to founders

Before we dive into the roadmap, let’s talk about YOUR responsibility in making this hire successful.

Your new marketing hire needs context to be effective. They need to understand your story, your customers, your product, and your vision. Don’t assume they’ll figure it out through osmosis - be intentional about sharing this information.

I wrote a detailed article about preparing for your first sales hire, and the same preparation and checklist applies to your marketing hire too.

Here’s what you need to prepare:

• Block time to tell your founder story and walk them through the business

• Facilitate introductions to sales, customer success, and other commercial team members

• Give access to customer data, CRM, sales conversations, and past marketing materials

• Set realistic expectations about timelines and results (marketing takes 3-6 months minimum to show meaningful impact)

• Commit to regular check-ins to provide feedback and stay aligned

Your new hire can’t read your mind. The more context you provide upfront, the faster they’ll be able to add value.

A note to the new marketing hire

Now, speaking to you directly - welcome! 🎉

While your founder has a responsibility to prepare for you, YOU have an equal responsibility to take initiative.

This is always true - but it’s even more important at a startup where there is less formal structure.

Don’t wait for information to be handed to you. Ask questions. Schedule your own meetings with the sales team. Request access to tools and data. Be proactive about learning the business.

Understand your situation

Before you start, you need to understand what type of marketing hire you are:

Scenario 1: There’s already a CMO (fractional or full-time) in place

If you’re joining a team that already has marketing leadership, much of the strategy work will likely be done for you. You’ll likely be more of an executor - implementing campaigns, creating content, managing tools, and bringing tactical expertise. This roadmap still applies, but your CMO will likely guide your priorities.

Scenario 2: You’re the first/only marketing person with no C-suite marketing leader

This is more common than you’d think. Many startups hire their first mid-level marketing person before they have a CMO. And often, the founder doesn’t have deep marketing experience themselves.

If this is you, here’s the reality: You’re going to need to flex up.

You might need to play a more strategic role than you were expecting. You’ll need to build the strategy, not just execute someone else’s. You’ll need to make big decisions about channels, messaging, and budget allocation. You’ll need to educate your founder on why marketing takes time and what realistic expectations look like.

This isn’t going to be easy. But here’s the upside: You’re going to expand your skills incredibly fast.

You’ll learn how to build from zero. You’ll learn how to influence leadership. You’ll get exposure to every part of marketing instead of just a niche specialty. These experiences compound quickly and will accelerate your career in ways a more traditional role won’t.

Try to embrace it as the amazing learning experience it is. Yes, it’s hard. Yes, you’ll feel in over your head sometimes. But that’s where real growth happens, too. 💪

Your roadmap starts here

This roadmap is your guide for the first two months (8 weeks), but it’s also a living reference document you’ll want to bookmark and revisit at months 2, 3, 4, and beyond.

Why? Because marketing is a long game, and inevitably, founders and sales teams get impatient. When someone asks “where are all the leads??” in month 3, you’ll pull this back out and remind everyone of what we all agreed to upfront.

Ok - let’s dive in!

Weeks 1-2: Build your foundation

Your first two weeks are all about learning. You can’t be effective if you don’t understand the business, the customers, and the team.

What you should focus on

A critical mindset: GTM multivitamins

Before we dive into the tactical weeks, read this article: GTM Multivitamins.

Here’s the core principle that should guide everything you do: As a startup with limited budget and bandwidth, every initiative you pursue should have multiple benefits.

This means:

• A case study helps close deals (sales enablement) AND becomes social media content (awareness)

• A blog post answers sales objections (enablement) AND drives organic traffic (top of funnel) AND fills your newsletter (nurture)

• Customer reviews build trust (enablement) AND improve conversion rates (enablement) AND provide content for social or ads (top of funnel)

As you build your plans in weeks 3-6, constantly ask yourself: How can this one initiative serve multiple purposes across the funnel?

Be creative and resourceful. Ask for budget when you truly need it, but look for ways to maximize impact without constantly requesting more resources. When you can show that one investment drives 3-4 different benefits, you’ll have a much easier time getting buy-in.

Week 3: Sales enablement - make selling easier

Now that you understand the business, it’s time to add value quickly. And the fastest way to add value? Help close the deals that are already in motion.

Your founder and maybe 1-2 AEs are handling sales conversations. Your job is to create assets that make their job easier, faster, and reduce friction for the buyer.

Create your sales enablement inventory

Start by making a comprehensive list of what exists and what’s missing. I wrote a whole article about sales enablement that you should read: Sales enablement 101.

According to Gartner research, these are the most common assets buyers reference in B2B sales:

• Customer reviews

• Personalized product demos

• Product documentation & user guides

• Online training

• Information about support capabilities

I’d also add:

• Case studies

• Blogs answering common sales questions or objections

• Pricing/packaging one-pagers

• Competitive comparison sheets

• ROI calculators or value frameworks

Your sales enablement process

1. Audit what exists - Make a spreadsheet of every sales asset you can find

2. Identify gaps - What’s missing? Maybe there are no case studies. Maybe product docs are outdated.

3. Get feedback - Use what you learned from your founder conversation and commercial team interviews. What would help them most?

4. Prioritize ruthlessly - What will have the biggest impact on close rates and deal velocity? Start there.

5. Create a plan - Map out what you’ll create, in what order, and by when

Remember: It’s easier to help close 10 existing opportunities than to generate 10 net new opportunities from scratch. That’s why we start here.

Week 4: Nurture marketing - activate what you already have

After you’ve mapped out your sales enablement plan, pivot to nurture marketing.

Here’s the insight: It’s easier to convert warmer leads already in your CRM than to drive net new leads to your CRM.

You likely have a database of people who’ve engaged with your company in some way - demo requests, website visitors, past conversations, event attendees. These are warmer than cold prospects, so let’s activate them.

Nurture tactics to consider

Tactic

When to use it

Why it works

Monthly newsletter

When you have consistent content and insights to share

Stays top of mind, positions you as a thought leader, gives you a reason to reach out

Product updates email

When you ship new features

Re-engages past prospects who said “no” for a specific reason you’ve now solved

Email drip campaigns

Trigger-based (e.g., after 5 website visits, after demo but no follow-up)

Automated nurture that moves leads down funnel without manual effort

These are not revolutionary tactics - but they are often basic things that the startup just hasn’t had the capacity to do yet. And they will make an immediate impact. Check out this article on the surprising ROI of email marketing.

Build your nurture plan

Map out:

• What you want to do (which tactics)

• Why you want to do it (the business objective)

• When it’s achievable to get it done (realistic timeline)

Consider what you learned about your buyers. Are they technical? Send them deep-dive product content. Are they executives? Send them strategic insights and ROI stories. Tailor your approach.

Week 5: Top of funnel strategy - build new pipeline

Now that you’ve got plans to help close existing deals (sales enablement) and activate existing leads (nurture), it’s time to think about generating net new pipeline.

Audit existing marketing activities

First, understand what’s already been tried:

• What have they done for top of funnel?

• What worked well?

• What didn’t work well?

• Have they done... anything? (Many startups haven’t - that’s okay!)

Develop your strategic point of view

Based on everything you’ve learned, build a hypothesis about the right approach. Should it be:

• Content-heavy strategy with lots of SEO-optimized blogs?

• E-book or lead magnet that captures emails in exchange for value?

• Webinars or virtual events that position you as experts?

• Partnerships that give you access to warm audiences?

• Paid ads on specific channels where your buyer hangs out?

• Founder-led content on LinkedIn or other platforms?

Research your buyer’s behavior

Don’t guess - research. Ask yourself:

• Where does this buyer consume content?

• What channels work best for reaching them?

• What pain points are they actively searching for solutions to?

• What format resonates most? (Long-form articles? Quick tips? Video?)

Use AI to help: ChatGPT or Claude can help you research buyer pain points, content consumption habits, and channel effectiveness for your specific ICP.

Remember: GTM multivitamins apply here too

As you build your top of funnel strategy, keep that multivitamin principle front and center. How can each initiative serve multiple purposes?

Examples:

• Founder thought leadership builds audience AND generates leads AND can be repurposed into longer form blogs or marketing emails

• A webinar generates new leads AND nurtures existing contacts AND creates repurposable content

• A blog post helps with SEO AND nurture email content AND answers sales objections

Think about how your top of funnel strategy can serve multiple purposes. That’s how you maximize impact with limited budget and bandwidth.

Build your top of funnel strategy

Document:

• Your recommended channels and tactics

• Why you think they’ll work for this specific buyer

• What success looks like (leading indicators)

• Realistic timeline and resource requirements

• How these efforts serve multiple purposes (the multivitamin effect)

Week 6: Present, align, and secure buy-in

Week 6 is about getting everyone on the same page and committed to your plan.

Prepare your presentation

Outline a clear presentation for the founder and commercial team covering your three priorities in order:

Priority 1: Sales enablement

• What gaps you identified

• What assets you plan to create

• Expected impact on close rates and deal velocity

• Timeline for delivery

Priority 2: Nurture marketing

• Current state of the database

• Your nurture strategy and tactics

• Expected impact on lead conversion

• Timeline and tools needed

Priority 3: Top of funnel

• Your recommended approach and why

• How it’s tailored to your buyer

• Expected leading indicators of success

• Timeline and resources required

Explain your strategic rationale

This is critical. Explain WHY you’re prioritizing in this order:

1. Sales enablement first = fastest value add. Shows you understand resource constraints and want to help close existing deals immediately.

2. Nurture second = easier to convert warm leads than generate cold ones. Demonstrates strategic thinking and a balanced approach.

3. Top of funnel third = longest timeline to results, but builds sustainable pipeline for the future which is important, too.

This sequencing shows the founder you can think strategically, prioritize ruthlessly, and focus on quick wins while building for the long term.

Request budget and tools

Present any budget requests alongside your strategy:

• Do you need to upgrade HubSpot from Starter to Pro? ($500/month)

• Do you need design software? (Canva, Figma)

• Do you need a content writer or freelance help?

• Do you need webinar software or paid ad budget?

Be specific about costs and what they’ll enable you to do.

Critical: Show the multi-funnel impact. Remember those GTM multivitamins? When asking for budget, demonstrate how the investment serves multiple purposes. For example:

“I’m requesting $500/month to upgrade HubSpot to Pro because it will enable:

• Automated nurture workflows (nurture marketing)

• Better lead scoring (sales enablement)

• Advanced email personalization (conversion optimization)

• Detailed attribution reporting (measuring all our efforts)”

This shows you’re being budget-conscious and strategic about maximizing ROI. You’re not asking for money frivolously - you’re showing how one investment unlocks multiple capabilities across the funnel.

Agree on timeline and expectations

This is perhaps the most important part of the entire presentation. Get everyone aligned on:

• When each initiative will launch

• How long before you expect to see results

• What realistic success looks like at 3, 6, and 12 months

Set expectations clearly: Marketing is a long game.

Most of your efforts will not have an immediate impact. That’s not a bug, it’s the nature of marketing and why we have marketing + sales. By managing expectations upfront, you protect yourself from future frustration.

Get formal agreement and commitment on the plan. Document it. You’ll need this later.

Weeks 7-8: Define success and establish cadence

You’ve got buy-in on your strategy. Now define how you’ll measure success and how you’ll communicate progress.

Identify leading indicators

For each priority, define the early signals that show you’re moving in the right direction:

Sales enablement indicators:

• Higher conversion rates through deal stages

• More closed-won opportunities

• Shorter sales cycles

• Sales team actively using new assets (track usage)

• Positive feedback from sales on asset quality and confidence in deals

Nurture marketing indicators:

• Email open and click-through rates

• More leads progressing from MQL to SQL

• Increased engagement from dormant database contacts

• More conversations started from nurture campaigns

Top of funnel indicators:

• Website traffic growth

• Content engagement metrics (time on page, scroll depth)

• New leads entering the database

• Lead quality scores (if applicable)

• Channel-specific metrics (LinkedIn followers, organic search rankings, etc.)

These leading indicators are what you’ll present quarterly to demonstrate progress, even before you see the lagging indicators (revenue, pipeline growth).

Establish meeting cadence

Set up recurring check-ins to maintain alignment:

Monthly meeting with sales:

• Review what’s working and what’s not

• Get feedback on assets and campaigns

• Iterate based on their real-time insights

• Surface new objections or questions to address in upcoming content

Quarterly review with founder and commercial team:

• Present leading indicators across all three priorities

• Show progress against the original plan

• Re-orient on goals and timelines

• Adjust strategy based on learnings

This regular cadence keeps everyone informed, maintains collaboration, and prevents the dreaded “what has marketing been doing??” question.

Managing expectations over time (months 2, 3, 4+)

Here’s the reality: Around month 2 or 3, someone is going to get impatient. The founder might ask “where are all the leads?” or sales might wonder why pipeline hasn’t doubled yet.

This is where you pull this document back out.

Remind them:

• We agreed marketing is a long game

• We prioritized sales enablement and nurture first (which take time to show ROI)

• Our leading indicators show we’re on track

• The timeline we agreed on hasn’t been met yet

Also show them the multi-funnel impact you’re already creating. Even if leads haven’t flooded in yet, you can demonstrate:

• “The case study we created has been used in 8 sales conversations AND is ranking on page 2 for our target keyword AND generated 50 social media engagements”

• “Our monthly newsletter has a 40% open rate AND is re-engaging dormant leads AND sales is forwarding it to prospects”

This evidence of multiple benefits from single initiatives shows you’re being resourceful and strategic with their investment - exactly what startups need.

This roadmap isn’t just an onboarding document - it’s a living reference tool that protects you and manages stakeholder expectations as you build marketing from scratch.

Have patience with the process

Most marketing initiatives take 3-6 months (or longer) to show meaningful results:

• SEO content takes 3-6 months to rank

• Nurture campaigns need time to warm up cold leads

• Brand awareness builds slowly over time

• Sales enablement impact compounds as more assets get created

The key is staying focused on your leading indicators and communicating progress consistently.

Trust the process you’ve built and committed to together. 🙏

Join a marketing community

Marketing is constantly evolving. New channels emerge, algorithms change, best practices shift. You can’t do this alone, and you shouldn’t try to. It’s lonely.

I strongly recommend joining a peer group or marketing community where you can:

• Ask questions and get advice from other marketers

• Stay current on trends and platform changes

• Learn what’s working (and not working) for companies similar to yours

• Build relationships with peers who understand your challenges

• Access templates, frameworks, and resources

If your startup is venture backed - your investors may even have portfolio specific communities you can join - find out.

Some other communities to consider:

• Exit Five - Community for B2B marketers

• Marketing Millennials - Community for modern marketers

The investment in community (many are free or low-cost) will pay dividends. You’ll learn faster, avoid common mistakes, and have a support system when things get tough. Marketing at a startup can feel isolating - connecting with peers makes it less so.

Sign up for relevant newsletters

Like this one 🙂

Here are a few others I like:

• Positioning with April Dunford

• Marketing Ideas

• Exit Five & Marketing Millennials mentioned above also have newsletters that are great

Final thoughts

You’ve got a solid two month (8-week) roadmap to ramp up as a marketing hire.

Remember:

✅ Learn deeply before you build (Weeks 1-2)
✅ Prioritize quick wins that help sales close deals (Week 3)
✅ Activate what you already have before chasing net new (Week 4)
✅ Build a smart top of funnel strategy based on research (Week 5)
✅ Get buy-in and set clear expectations (Week 6)
✅ Define success metrics and communication cadence (Weeks 7-8)
✅ Resurface this roadmap when people get impatient
✅ Join a community or newsletter distros for ongoing learning and support

You’ve got this! 🚀

I had an epiphany on vacay last weekend…I’ve talked a LOT about what founders can do to support their new reps before you hire them - but then totally failed to talk about what to do after!

So here is your very detailed playbook. Let me know what you think! 😉

Your new sales hire’s first 6 weeks: An onboarding roadmap

A tale of two onboardings

I’ve been a new sales hire a few times in my career, and the difference between those experiences taught me everything I need to know about what makes or breaks early sales success.

Company A had their act together. They had everything from my pre-hire checklist ready before I walked in the door - clear positioning, sales collateral, a loaded CRM with call recordings, case studies, the works. I hit 150% of quota within six months and exceeded 200% within a year.

Company B had less than 30% of that checklist completed when I started. There was no clear targeting or positioning - we sold to everyone, minimal collateral, a spreadsheet for a CRM, and a founding team who thought I should just ‘figure it out’. I went 12 months without closing a single deal.

Same salesperson. Wildly different outcomes.

The difference? Preparation.

For founders: Preparation is only half the battle

If you’re a founder preparing to make your first sales hire, go back and review this pre-hire checklist. Make sure you can check off at least 80% of those items before your new hire’s first day. It will 5x your odds of success.

But here’s the thing: even if you do everything right, your new sales hire has equal responsibility to be proactive, resourceful, and self-directed. In a startup, they should come in with an understanding that nobody is going to spoon-feed them a perfect onboarding experience. They need to take ownership of getting themselves up to speed as quickly as possible.

This guide is designed to be a resource you can hand to your new sales rep on day one. It gives them a clear roadmap for their first six weeks and shows them exactly how to take pressure off you while ramping up effectively.

P.S. - While it’s their job to be proactive, it’s your job to set that expectation on day 1.

Alright, new sales hire - this part is for you

Congratulations on the new role! You’re joining a startup, which means things are going to move fast, feel chaotic at times, and require you to be incredibly self-sufficient.

It’s going to be hard - but the upside is that you’re going to 10x the speed of your professional growth.

The founder who just hired you is already wearing ten hats, and they need you to start contributing as quickly as possible. That doesn’t mean you need to close deals in week one, but it does mean you need to be proactive about learning the business, taking work off their plate, and organizing yourself to win.

Here’s your roadmap for the first six weeks. Follow this plan, and you’ll both impress the founder who just hired you + set yourself up for success.

Week 1: Get set up and oriented

Your first week is all about getting access, gathering information, and having the first of many really important conversations with your founder.

Get access to everything

Let’s start with the basics. Make sure you know what systems the team is using (a full list) and have logins to all relevant systems:

• CRM (HubSpot, Salesforce, etc.)

• Lead data tools (Apollo, ZoomInfo, etc.)

• Sales engagement platforms (Outreach, SalesLoft, etc.)

• Any other go-to-market technology the company uses

If there’s no documented list of the tech stack, create one. You’ll need it later and the founder will thank you.

Collect all sales collateral

Ask for copies of all sales assets:

• Sales decks

• One-pagers

• Case studies

• Proposal templates

• Email templates

• Any other assets they’ve created

Don’t worry about quality yet - just gather everything that exists.

Request market research

Ask the founder for any market research, industry analysis, or competitive intelligence they’ve compiled. Understanding the landscape will help you speak more credibly to prospects.

Prepare for your founder onboarding meeting

Before you sit down with the founder, do your homework:

• Study their LinkedIn thoroughly - Where did they work before? What’s their career story?

• Listen to any podcasts or press interviews they’ve done - How do they talk about the company? What points do they emphasize?

• Come prepared with questions - Show them you’re serious about ramping quickly

Have a deep founder onboarding meeting

This might be the most important meeting of your first month.

Use call recording software (Fireflies, Otter, etc.) so you can listen back to this conversation multiple times without making the founder repeat themselves.

Here’s what you need to extract from this conversation:

The origin story - Ask the founder to tell you how the company got started. This story is probably a huge part of what makes them such an effective salesperson. You need to learn it and be able to tell it yourself.

• Why did they build this?

• What challenge did they see that needed solving?

• What’s their personal connection to the problem?

Immediate priorities - Get crystal clear on:

• How can I help you immediately?

• What are your expectations of me in the first 30, 60, 90 days?

• What does success look like?

Sales intelligence - Learn about:

• The most common objections or questions you’ll get in sales conversations

• What typically makes deals stall or fall apart?

• What makes deals move forward quickly?

• Any insider knowledge about the market, competitors, or customers

Suck as much intellectual property out of the founder’s brain as you possibly can. They know things you need to know, and this is your chance to download as much of it up front as you can.

Set up a weekly sales pipeline review

Ask the founder if there’s already a regular pipeline review call. If there is, get yourself added to it. If there isn’t, set one up yourself.

Here’s why this matters: you need a recurring touchpoint with the founder to ask questions, provide updates, review deals, and get feedback. A weekly pipeline review creates that structure.

If you’re creating this meeting from scratch, impress the founder by setting the agenda yourself:

• Pipeline coverage (overview of deals in each stage and forecast)

• Notable deal updates (what moved forward, what stalled, what closed)

• Blockers or questions you need help with

• Wins or learnings from the week

This call becomes your regular forum for staying aligned with the founder and continuously iterating on what’s working.

Start exploring the CRM

Do an initial walkthrough of the CRM. Don’t go deep yet - just familiarize yourself with how it’s organized and what data exists.

Week 2: Learn the business deeply

Week two is about immersing yourself in the business so you truly understand what you’re selling and who you’re selling to.

Deep dive into the CRM

Now it’s time to really dig in:

• Read through emails on closed-won deals

• Listen to sales call recordings (as many as possible)

• Pay attention to how the founder talks, what questions prospects ask, how objections are handled

• Look for patterns in what works and what doesn’t

Study the current customer base

Pull a list of all active customers and get familiar with those names. You want to be able to quickly rattle off logos or reference specific customers in your sales conversations.

As you study the customer base, look for patterns:

• Are most of them in healthcare? Financial services? Tech?

• What size companies are they?

• What titles are the main decision makers?

• What use cases for purchasing are most common?

Use these patterns as your guide for identifying new prospects. Your best future customers will look a lot like your best current customers.

Listen to customer feedback

If there are any recordings of current customer interviews - maybe from a case study project or investor diligence - get copies and listen to them. Hearing directly from current customers about why they bought, what they love, and where there are gaps is invaluable.

If no recordings exist, ask the founder or a team member to introduce you to 2-3 current customers. Schedule calls to interview them.

The nice thing about these calls is they’re already sold - you’re not pitching them anything. You’re purely using the conversation to learn how to speak to their peers in future sales conversations.

Ask questions like:

• What problem were you trying to solve when you bought this?

• Why did you choose us over alternatives?

• What do you love about the product?

• What’s missing or could be better?

• How would you describe us to a colleague?

Meet with every client-facing team member

Set up one-on-ones with:

• Anyone in marketing

• Anyone else in sales

• Anyone in customer success or support

• Anyone in product

Ask them:

• What do you feel is working well about the product or our sales approach?

• What do you feel isn’t working?

• What do you think I should know as a new sales person?

Use all of this information to inform how you position, sell, and collaborate with these team members.

Week 3: Jump in and help immediately

By week three, you should know enough to start taking work off the founder’s plate. This is critical - the faster you can relieve pressure, the more valuable you become.

Review open deals in the pipeline

Go through every open opportunity in the CRM:

• Where is each deal in the sales process?

• What’s the next step?

• What’s blocking progress?

• Which deals has the founder been meaning to follow up on but hasn’t had time?

Identify where you can help right away

The founder is probably overwhelmed and juggling 100 other things simultaneously. Look for opportunities where you can:

• Project manage deals through the pipeline

• Handle follow-ups and scheduling

• Send contracts or proposals

• Coordinate demos or meetings

• Research accounts and help prep for calls

You don’t need to close these deals yourself right now. Just take tasks off the founder’s plate and keep things moving forward.

Start taking pressure off the founder ASAP

The goal this week is simple: make the founder’s life easier. Show them you’re capable, organized, and ready to run with things. This builds trust and gives you more autonomy going forward.

Week 4: Build strategy and take inventory

Now it’s time to organize your approach to new business and assess what you need to be effective.

Pull your target lists

Your fastest paths to revenue now and always are:

Lost opportunities - Pull a list of every closed-lost deal in the CRM. These are warm leads who already know the company. Many of them are worth revisiting.

Job changes - Pull a list of anyone associated with a past deal who has since changed jobs. If your tech stack includes Apollo, they have a great job change report. These people are at least familiar with your product and might have a need at their new company.

Network referrals - This is the warmest channel of all:

• If you have your own network, map it out and identify potential prospects

• If you don’t, mine the founder’s LinkedIn connections for potential prospects

• Make it easy for the founder to make introductions by drafting outreach templates they can personalize and send

Organize your warm lead strategy

Don’t start with cold outreach yet. The three channels mentioned above are much warmer because they have some familiarity with a person at the company or the company itself.

Spend time building a strategy for how you’ll tackle each channel:

• Who will you reach out to first?

• What’s your messaging?

• What’s your cadence?

• How will you track everything?

Get organized now so you can execute efficiently in week five.

Take inventory of tech stack and sales assets

Now that you’ve been here a month, you have a much better sense of what’s missing.

Tech stack audit:

• Are you being asked to do cold outbound without a lead data tool? Maybe you need to request Apollo.

• Is the CRM missing key features or integrations? Maybe you need to upgrade your HubSpot license.

• Do you need a sales engagement platform to automate sequences?

If you need additional technology, put together a business case that includes:

• What tool you need and why

• The cost and contract term

• How it will directly impact your ability to generate revenue

• Estimated ROI calculation if possible

Sales assets audit:

• Does the sales deck look professional, or does it need a redesign?

• Are there enough case studies? (You’ll definitely need them to close deals)

• Are email templates and one-pagers up to par?

• What else is missing that you know you’ll need?

Make a prioritized list and present it to the founder. Be specific about what you need and why. If there is something on the list you can own - offer to own it. Show them you’re thinking strategically about what it takes to win and you’re willing to do things outside of your immediate role.

Week 5: Execute on warm outreach

By week five, you should be organized, oriented, and actively taking pressure off the founder. Now it’s time to start building your own pipeline.

Launch outreach to warm leads

Start executing on the strategy you built in week four:

• Reach out to lost opportunities with a fresh perspective

• Connect with people who changed jobs and know the product

• Work with the founder to get introductions through their network

Remember: these are warm leads. Your conversion rates should be higher than cold outreach, and your sales cycles should be shorter. We love that for you.

Continue supporting active pipeline

Don’t drop the ball on the deals you picked up in week three. Keep moving those forward while you work on building new pipeline.

Track everything

Make sure you’re logging all activity in the CRM:

• Emails sent

• Calls made

• Meetings scheduled

• Responses received

This data will help you (and the founder) understand what’s working and what’s not.

Week 6: Full execution and your first mark-to-market

By week six, you should be in full execution mode. But you also need to take stock of where you are and have an honest conversation with the founder about what’s working and what’s not.

Continue all warm outreach activities

Keep working your lost opportunities, job changes, and network referrals. These channels should be generating meetings and moving deals into your pipeline.

Refine your approach based on early feedback

Pay attention to what’s working:

• Which messages are getting responses?

• Which objections are you hearing most often?

• What’s resonating with prospects?

Adjust your approach accordingly. Sales is a game of constant iteration and improvement - especially at a startup.

Schedule a separate one-on-one with the founder

This is different from your weekly pipeline review. This is a deeper, more strategic conversation where you do a mini “mark to market” on your first six weeks.

Come prepared to discuss:

What you’ve accomplished

• Deals you’ve supported or moved forward

• Pipeline you’ve generated

• Systems or processes you’ve improved

What you’ve learned

• About the product, customers, and market

• What’s working in the sales process

• What’s not working

Where there are still gaps

• In your understanding of the product, market, or sales process

• In the tech stack or sales assets you need to be effective

But here’s the key: Don’t just ask for things. Ask for timelines.

If you need to purchase Apollo, don’t just ask for permission. Ask when they can have a decision for you or when you can make the purchase.

If you need a sales deck redesigned, don’t just ask for approval. Try to get clear on when that’s going to be done.

Be specific. Be solution-oriented. Show you’re thinking about execution, not just making requests.

Get clear on your quota

By week six, you should have a very clear understanding of your quota. If you haven’t discussed this yet, bring it up in this meeting.

More importantly, use what you’ve learned in your first six weeks to assess whether that quota is achievable:

• Based on average deal size, how many deals do you need to close?

• Based on conversion rates you’ve observed, how many opportunities do you need in pipeline?

• Based on your current activity levels, is that realistic?

If you don’t think the quota is achievable based on what you’ve learned, flag it now. Don’t wait six months to have this conversation.

I’ve written at length about how to manage expectations on this. Use this framework to back into the feasibility of the goal they’ve set for you.

Discuss when you can realistically close your first deal

This is a critical conversation to have. When can both you and the founder realistically expect you to close your first deal?

This timeline depends on several factors:

• The current state of their GTM maturity (systems, assets, etc)

• Average sales cycle length

• How warm your initial pipeline is

Setting this expectation now prevents frustration and misalignment later.

Beyond week 6: The ongoing cadence

Your work doesn’t stop at week six. Here’s what you need to know about the months ahead.

Keep your weekly pipeline reviews going

This should remain a standing meeting. Use it to continuously ask questions, provide updates, review deals, and iterate on what you’re doing.

Schedule a separate mark-to-market conversations every 4-6 weeks

For your first six months, you and the founder should have these deeper one-on-ones every 4-6 weeks. These aren’t pipeline reviews - they’re strategic check-ins where you:

• Assess progress toward quota

• Discuss what’s working and what’s not

• Adjust strategy as needed

• Address any gaps in resources or support

• Reset expectations if necessary

This ongoing cadence is the only way you’re going to collaboratively move past challenges and stay aligned.

If you’re not meeting objectives after six months...

If after six months you’re still not hitting your targets (or showing leading indicators you’re close), it’s time for a more serious conversation.

It could be partially your fault (effort, approach) and/or partially the founder’s fault (product-market fit, pricing, support, resources).

But having a regular cadence to review, discuss, and reset expectations is what allows you to course-correct before you hit that six-month mark.

Final thoughts

The first six weeks at a startup sales role can feel overwhelming. You’re drinking from a fire hose, there’s no perfectly structured training program, and expectations are high.

But if you follow this roadmap - if you’re proactive, resourceful, and focused on adding value quickly - you’ll set yourself up for success.

Remember the three keys:

1. Be a sponge. Absorb everything you can about the business, the product, the customers, and the market. The more you know, the better you’ll sell.

2. Take pressure off the founder immediately. Don’t wait to be told what to do. Look for ways to help and jump in.

3. Start with warm leads. Lost opportunities, job changes, and network referrals are your fastest path to revenue. Master those channels before you tackle cold outbound.

You’ve got this. Now go make it happen.

A massive thank you to my wonderful guest authors for helping me keep this thread alive through maternity leave. 🙏

• Elles Skony - master community builder & people leader

• Jared Gibson - founder brand & thought leadership expert

• Richard Washington - GTM talent architect & advisor

• Corrina Owens - ABM aficionado & architect

Alright - we’re going back to basics this week. Because every. single. time. I audit a new startup (30+ now), I find the same RevOps issues.

And here’s the thing, RevOps is the foundation you need for successful AI implementation AND successful hiring. And you’re gonna need both to scale.

It’s non-negotiable.

Let’s dive in. 🏊‍♀

Why RevOps is your secret weapon (for both humans and AI)

I’ve been hearing two things on repeat lately from founders:

1. “We need to hire [insert GTM role here]”

2. “We need to figure out how to use AI to help with [sales/marketing/everything]”

Here’s the thing - both of those things will fail (or at least seriously underperform) without one critical ingredient ➡ solid RevOps.

Think about it this way - whether you’re bringing on AI agents to help qualify leads or hiring a new AE to close deals, they both need the same thing to be successful: clean data, clear processes, and the right tech stack to support them.

You wouldn’t hire a sales rep and not give them a CRM, email access, or any information about your ICP, right?

The same goes for AI. It’s not magic - it’s only as good as the foundation you give it to work with.

So before you make your next hire OR implement that shiny new AI tool, let’s make sure your RevOps house is in order. 🏠

Why RevOps infrastructure is non-negotiable for success

Here’s what I’ve seen happen over and over:

Scenario 1: A founder hires their first sales rep. That rep has no documented sales process, no clean CRM data to prospect from, no call recording to learn from past deals, and no clear understanding of what “good” looks like. Three months later, pipeline growth is flat, conversions are dropping, and the founder is back in every deal.

Scenario 2: A founder implements an AI SDR tool to help with outbound. But the ICP data in their CRM is a mess - missing job titles, duplicate accounts, outdated contact info. The AI starts sending emails to the wrong people with irrelevant messaging. The tool gets blamed, but the real issue was the foundation.

Sound familiar?

RevOps isn’t just operations for operations’ sake. It’s the infrastructure that makes both your human talent AND your AI tools actually effective.

When you have solid RevOps:

• New hires ramp faster because they have clear processes, clean data, and documented best practices

• Marketing is more effective because you can properly segment, target, and nurture your network

• AI tools perform better because they’re working with quality inputs and structured workflows

• Your entire GTM team moves faster because everyone has the same source of truth

• You can actually see what’s working (and what’s not) with real data instead of gut feel

The Minimum Viable Tech Stack

Okay, let’s get practical and tactical. My speciality.

If you’re just getting started with RevOps, or if you need a mark-to-market, here’s what you actually need - no fluff, no “nice to haves,” just the essentials.

The 6 Essential Tools:

1. CRM - Your source of truth for all customer and prospect data

2. Sales Engagement Tool - Sequences, templates, and outreach automation

3. Marketing Automation Tool - Nurture campaigns, marketing comms and automation

4. Lead Data - Accurate contact and company information to find new leads and to continuously enrich your CRM

5. Knowledge Management System - Your internal wiki/intranet for processes, playbooks, and documentation

6. Call Recording Software - Record, transcribe, and analyze your sales conversations

Now here’s where it gets better - you don’t need 6 different tools to cover all these bases.

My Recommended MVT (Minimum Viable Tech Stack):

• HubSpot - This checks off at least THREE boxes: CRM, sales engagement, and marketing email/automation. Yes, there are other CRMs out there, but HubSpot is the most cost-effective and robust (cost to value) out there with a generous startup discount.

• Apollo - The most cost-effective lead data tool out there. Clean contact data, company information, and integrates directly with HubSpot. You could also use Apollo for sales engagement and call recording.

• Notion - Hands down the best budget-friendly knowledge management solution. Use it for your sales playbooks, process documentation, onboarding materials, and team wiki.

• Fireflies - My favorite call recording tool (though Otter, Grain, etc all work too). Just make sure whatever you choose has a native integration with your CRM. Fireflies plays nicely with HubSpot and won’t break the bank.

Total cost for this stack? You can get started for under $500/month for a small team.

Compare that to the cost of a bad hire or an underperforming AI tool because you didn’t have the foundation in place. No brainer.

The RevOps Starter Checklist: 3 Things to Get Right Immediately

Once you have your minimum viable tech stack set up, here’s what you need to implement right away. These are table stakes - if you don’t have these in place, everything else will be harder than it needs to be.

1. Core Data Hygiene

This is the foundation of your foundation. Your CRM data needs to be clean, enriched, and maintained - not just at setup, but continuously.

What you need:

Data Enrichment - Make sure you’re enriching missing or incomplete data like job titles, company industries, company size, etc. This isn’t just for pretty reports - you need this to segment your audiences properly for both outbound prospecting AND email marketing.

For example, if you’re targeting “VPs of Sales at Series A-B SaaS companies with 50-200 employees,” you can’t do that if half your records are missing job titles or company size data.

Most lead data tools (like Apollo) can help with enrichment, or you can use HubSpot’s data enrichment features which just got a glow up.

Deduping - Duplicate records are the enemy of good data. Have someone on your team set up a monthly process (put it on your calendar right now) to review and dedupe your accounts and contacts.

Why monthly? Because duplicates creep in fast - from form fills, manual entry, integrations, imports, you name it. The longer you wait, the worse it gets and the harder it is to clean up.

2. Pipeline Hygiene

If your CRM is the house, your pipeline data is the rooms where the actual work happens. This is the data you collect, store, and manage on your deals/opportunities.

You need to be tracking the right information on every deal so you can:

• Forecast accurately

• Identify bottlenecks in your sales process

• Revisit or nurture lost opps

• Understand what’s working and what’s not

• Coach your team effectively

….and more.

I’ve written a few related articles on what to track and manage on your deals, which you can check out here:

• When to create and close deals

• How to setup your deal stages

• Deal metrics to measure

A tip to keep yourself and your team honest? Setup a dashboard to show you exactly which deals are missing critical information. Reports on this dashboard would include:

• Deals missing an owner

• Deals missing an amount

• Deals missing a source

…and so on. Schedule this dashboard to be sent out weekly to everyone who owns deals. It’s like a naughty list that you want to make sure you aren’t on.

3. Capture ALL Client Interactions in Your CRM

I don’t care how good someone’s memory is - you can’t build a scalable revenue engine on people’s brainpower alone. Everything needs to live in your CRM so it’s searchable, referenceable, and available to your entire team (present and future).

How to make this happen:

Connect your Email & Calendar to your CRM - Set up your email and calendar to automatically sync with your CRM. HubSpot makes this stupid easy - every email and meeting with a prospect or customer gets logged automatically. No manual entry required.

This does two things:

1. Keeps a complete record of all touchpoints with each account

2. Surfaces communication in context when someone else on your team needs to jump in

Use Call Recording Software - This is non-negotiable in 2025. Every sales call should be recorded, transcribed, and stored.

Why?

Because:

• New hires can listen to real calls to ramp faster

• AI can analyze call patterns to identify what’s working

• You can coach based on actual conversations, not hearsay

• You never have to rely on someone’s “rough notes” from a key discovery call

The key: Make sure your call recording software is set up to automatically feed call summaries and key insights into your CRM. Fireflies does this beautifully with HubSpot - every call gets summarized and logged to the deal record automatically.

The Bottom Line

Whether you’re hiring your first sales rep, implementing an AI SDR, leveraging AI for content creation, win/loss analysis, etc - they’re only going to be as good as the RevOps foundation you give them to work with.

Clean data, clear processes, and the right tech stack aren’t “nice to haves” anymore. They’re the baseline requirement for any GTM motion that’s going to scale.

The good news? You don’t need a massive budget or a dedicated RevOps FTE to get started. You just need to commit to doing these basics from day one. If you’re late - start today.

Start with the minimum viable tech stack. Get your data hygiene, pipeline hygiene, and interaction capture in place. Then build from there.

Your future hires (human and AI) will thank you.

Some other related articles

• Preparing for your first sales hire: a checklist for founders

• How to reduce your odds of failure with your first sales hire

The key takeaways -

• Traditional digital marketing is broad. Account-based marketing is precise. ABM is focused on targeting a sliver of your TAM called TRM (total relevant market).

• Contrary to popular belief, ABM is not only effective for enterprise sales and can work for SMB and mid-market as well. But for enterprise, it really should be table stakes.

• Getting started with ABM doesn't require any new technology (right away). You already have everything you need to test this right now.

• The most successful ABM campaigns have two things in common 1) the voice of your customer (your best sellers) and 2) IRL experiences - go beyond digital.

• Your first sign it’s working is engagement data. But you need a strategy and process to act on that engagement data for it to drive the ultimate outcome —> more revenue. A custom GPT (+ Corrina) might be able to help.

More on the last point ^ in this week’s final article.

Enjoy!

How to know if ABM is working + custom GPT

“This is all great, Corrina, but how will I know if ABM works?”

First…

1. You’ve aligned on the ICP and buying signals

2. You’ve picked your target accounts

3. You even got your team to buy-in to this thing called ABM

So now what?

💡 Now, you start to get activity from these accounts. That engagement data is the first sign it’s working. People from your target accounts are responding, clicking, viewing, and RSVPing.

But simply collecting the engagement data is not enough, you have to know what to do with it.

Unfortunately, I’ve seen plenty of companies build the most beautiful tech stacks in the world, with dashboards combining reports from all their vendors, designed to surface every signal under the sun.

But when those systems don’t reflect how your business actually thinks and sells? That data just sits there and gets ignored altogether.

Sound familiar?

That’s why I started building a custom GPT for ABM programs

One of my clients had all the data: outreach metrics, campaign engagement, and firmographic intent, but the person managing the account had no idea where to focus—or what actions to take next when looking at these account engagement reports.

So I trained an LLM to help.

Not just on what signals to look for (like case study views + recent hiring + high-fit industry)... but on how we respond when that pattern shows up. Not with a generic sequence, but with a thoughtful, contextual touchpoint rooted in the buyer’s world.

After a dozen or so iterations of me providing feedback, correcting the LLM, I felt confident that it could get an account rep 99% of the way there for them, without them having to manually sift through reports.

They’d drop in their weekly view, and the LLM would surface quality engagement and recommendations for next steps. 🙏 

Curious what it looks like in practice? Take a peek at the custom GPT here. 👀 

Finally, after you start 1) collecting engagement data and 2) acting on engagement data with intention…you should ultimately see more deals created + a faster sales cycle (aka more revenue).

Now you’re reaching the right people at the right time with the right context. 👏 

If you stuck around with me this long, thank you. I hope I was able to paint a clearer picture of what ABM can look like in practice and maybe even what to avoid when you’re trying to prove it out.

Need some more help getting started?

I help Seed to Series C B2B SaaS companies launch account-based GTM motions that don’t just look good on paper, but actually help revenue teams hit their target, even with lean headcount.

And if you’re looking for a bit of help or guidance for how to do this at your org, I’d love to chat. Please reach out anytime on LinkedIn, or feel free to grab a spot on my calendar.

Book time with Corrina

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

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Thanks for reading GTM for Startups by Jess! This post is public so feel free to share it.

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So far she’s covered -

• What is ABM and why it works

• How to get started 

And this week she’ll share some real life examples of ABM plays she’s run that have worked super well…no ad spend required.

Let’s do it.

Real ABM plays that work - zero ad spend required

So once you…

1. Pick out your 50-100 test accounts

2. Build your initial hypothesis 

3. Identify your control group

…then it’s time to engage your test accounts. And you might be wondering…

“How do I do that?” 

Some examples include: 

1. Running paid ads exclusively to specific people at the test companies

2. Targeted outreach possibly directing them to a personalized landing page

3. Direct mail to key stakeholders

4. Personalized invites to curated executive dinners

…and the list goes on!

But the best ABM campaigns I’ve ever run didn’t cost a dime in ad spend. They had two things in common - 

1. They leveraged the customer’s voice (your best seller)

2. They incorporate in-person experiences (not solely digital)

Your best sellers are your customers - use them

During my time at Gong, I piloted a peer-to-peer matching program that allowed late-stage prospects to speak directly with our most loyal customers at a critical point.

A competitor had just acquired another company and could now offer a comparable solution—for free. And not just one year free. Three.

Our enterprise reps were losing deals not because our product didn’t stand out, but because the price tag didn’t stand a chance. It was obvious, to really compete, we needed something different.

This program wasn’t a one-off referral email or cherry-picked testimonial. It was a private, curated space where late-stage prospects could meet directly with real users. And these closed-door conversations were facilitated entirely by marketing.

One of those customers even ended up getting a job offer from the prospect. 

That’s the kind of trust currency you can’t fake.👆

[This community-led bottom-of-funnel play still drives 150% YoY growth.]

Go beyond digital marketing with in person experiences 

Trying to cut through the digital noise in 2025 is like trying to top Beyoncé on the country chart…

You can try, but you're likely not walking off with a Grammy.

That’s why digital alone won’t cut it. And why I always build ABM programs that incorporate in-person experiences.

Last year, I ran a series of executive dinners for a client that was known almost exclusively for their digital presence.

And yet?
→ Post-event demos spiked
→ 85%+ ROI per dinner

Why these work

Campaigns like these work because they’re rooted in the human experience. They build trust and affinity. 

When we're solely focused on digital mediums, it's much easier to forget those core principles. But that’s the differentiator that most ABM plays are missing.

In our final issue, we’re going to talk about what success actually looks like—how to measure impact, maintain momentum, and know if your ABM motion is working.

P.S. Want to chat about what ABM could look like at your org? Let’s connect.

Book time with Corrina

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

Subscribe for weekly education, ideas, and frameworks

In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

Subscribe now

Thanks for reading GTM for Startups by Jess! This post is public so feel free to share it.

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My primary goal with this newsletter is to make go-to-market education and advice approachable, tactical, and ‘doable’ for startups.

No big words, fluffy advice, or expensive investments.

Just simple, actionable, and realistic playbooks you can run with a small(er) budget and team.

Corrina’s advice hits the mark.

Enjoy 🙂 

How to get started with ABM

Hopefully, you’re at least ABM curious after last week’s ABM intro. And you might be thinking…

”Do I need to buy ANOTHER tool for this, though?”

Maybe, but not right away. I know you’ve seen the pitch decks and read the case studies…every tool promises the same:

→ Do more with less
→ Stop chasing bad leads
→ Make you 10x more efficient

And before you know it, you’re knee-deep in multiple implementations, with zero adoption, and staring at the same problem you had before you bought the tool.

It wasn’t the strategy that failed. It was the expectation that the platform would do the work.

So, before you spend any money on any new tool, try starting with what you already have:

1. Dig into your CRM

Find shared traits across your won/lost deals— including job titles, tech stacks, objections, campaign touchpoints.

2. Build a test list of 50–100 accounts

Prioritize accounts with strong first-party signals. Here are 2 first-party signal-based campaigns I’d recommend implementing. 

3. Pick a hypothesis and test it

Example: “Past opps who lost to Competitor X may now be up for renewal.” Surround those accounts with tailored content, a direct mailer, and an exec intro.

4. Run a control group

No matter how lean your campaign, track what would’ve happened without ABM. Start simple.

Remember…

ABM ≠ Campaign. 

ABM = GTM Operating Model.

“Campaign thinking” is quarterly, marketing-owned, and optimized for form-fills. ABM thinking is weekly, cross-functional, and measured by pipeline impact.

Next week, I’ll walk through what happens when you hand the mic to your best sellers—your customers—and how to design ABM plays that build trust before the first sales call.

See ya there!

P.S. Want to chat about what ABM could look like at your org? Let’s connect.

Book time with Corrina

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

Subscribe for weekly education, ideas, and frameworks

In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

Subscribe now

Thanks for reading GTM for Startups by Jess! This post is public so feel free to share it.

Share

This week we’re kicking off the first of a four part series from the lovely and talented Corrina Owens on all things ABM (Account Based Marketing).

Corrina is a fractional ABM specialist who works with B2B SaaS companies to build and monetize ABM programs that scale. She’s one of the best marketers I know who has worked at or with some of the top brands in tech (Gong, Aptivio, Demandbase, and more).

If you haven’t heard of ABM yet…Corrina will explain it to you. And if you’ve heard of it but aren’t sure how to really ‘do it’ - she’ll cover that too.

Let’s do this.

Account Based Marketing (ABM) 101

I didn’t start my career planning to specialize in ABM. Like most marketers in B2B SaaS, I got thrown into messy handoffs, broken pipeline workflows, and eye-rolls from sales the moment I said the word “campaign.”

I quickly learned: the only way to get traction wasn’t through one-off launches or tools—it was by embedding myself in the revenue team.

→ Sitting in on territory planning

→ Joining pipeline review meetings

→ Listening to sales calls

→ Showing up in Slack like a partner, not a presenter

That’s when I stopped being “marketing” and started being part of the deal team.

So, what is ABM, really?

🚫 ABM is not a campaign.

✅ It’s a go-to-market operating model.

ABM vs traditional marketing

The real difference between traditional marketing and modern account-based marketing comes down to focus—who you’re targeting, when you’re reaching them, and why they’re relevant right now.

Traditional marketing tends to cast a wider net. Think: always-on, persona-based content distributed across multiple channels. It’s more about showing up wherever your potential buyers live, regardless of timing or readiness.

Modern ABM, on the other hand, is about precision, identifying the sliver of your total addressable market that’s not just a fit, but actively looking for a solution that you sell and then engaging them with timing, context, and intent that aligns with what they actually care about right now.

Here’s how I like to think about it:

• Total Addressable Market (TAM) = everyone who could buy from you

• Total Relevant Market (TRM) = who might likely buy from you right now

ABM = how you act on that TRM window of opportunity. 👆️ 

For example:

Say you sell a point solution for government agencies to streamline CRM workflows. Your TAM might include every federal contractor at agencies of a certain size. But if you know an agency is in the middle of implementing a new CRM (like Salesforce), that’s a signal. That’s when you can be intentional about surfacing the right content, activating the right channel, and pulling in the right reps for that particular account.

I always say: ABM is just as much about who you're targeting as it is who you are not.

When you’re working with a finite budget and finite sales capacity, it’s just as important to disqualify low-fit accounts as it is to prioritize the right ones.

When does ABM make sense?

Contrary to popular belief, I don’t think ABM is just for enterprise targets. I’ve helped companies run lean, high-performing ABM motions across smaller deal sizes as well —but it does shine most when:

• You’re moving upmarket

• Your ACV is $50K+

• Your sales cycle is long or multi-threaded (ie multiple decision makers)

That’s when it makes the most sense to align tightly across Marketing, Sales, and CS—and build programs that flex as part of a full GTM motion. 

ABM is a strategy - not a tool or tech stack

There are a whole host of ABM specific software providers out there but it’s important to understand that ABM is not a tool or tech stack implementation.

It’s an operating model. It’s a strategic way of ‘going to market’.

When ABM doesn’t work, it’s almost never because of the tech you’re using (or not using), and almost always because the company:

• Doesn’t know who their ICP is (or can’t agree)

• Doesn’t have a consistent sales process

• Can’t break out of team silos

In fact, I recently had a marketing head of a $12.7 million SaaS company say:

“We’re kind of idiots when it comes to ABM… maybe don’t include that in the recording.”

And after just 30 minutes of chatting, they saw it differently:

 “This is very helpful. It’s a relief to hear someone validate ABM as a good idea.”

ABM isn’t magic. But when you align your team around the true revenue impact—not vanity metrics—and stop expecting a tool to do the strategy for you, it can become the most powerful GTM motion in your playbook.

Next week, we’ll dive into how to build your first ABM motion using what you already have—your CRM, a spreadsheet, and one or two buying signals. 😉 

See ya there!

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

Subscribe for weekly education, ideas, and frameworks

In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

Subscribe now

Thanks for reading GTM for Startups by Jess! This post is public so feel free to share it.

Share

If you’re new here, Rich dropped a ton of wisdom on talent and recruiting this month. He covered -

• 5 Common GTM hiring mistakes

• Why entrepreneurs need intrapreneurs around them

• Founder led sales transition playbook

And finally, this week he’ll break down his homegrown Multiplier Matrix framework.

Next month, the fabulous Corrina Owens will be schooling us on all things ABM (Account Based Marketing)! And then after that - we’re back to regularly scheduled programming from yours truly.

I can’t tell you how much I appreciate all of the love and support I’ve received for me and my little guy during this big life moment. ❤️ 

Enjoy! See ya next week!

The Multiplier Matrix: A framework for top talent

If you’ve been in founder or leadership circles for more than five minutes, you’ve heard someone say,

“We only hire A players.”

Sounds great. But here’s the problem = if you ask ten people to define what an A player actually is, you’ll get a hundred different answers.

Some will say it’s your “top 10% performers.” Others will say it’s “people who go above and beyond”

The reality? Very few companies can define it clearly enough to actually hire or coach against it.

In fact, as we shared in week 1 of this 4 partners = research from Sequoia shows only 15% of companies have defined the attitudes and behaviors that make someone a high performer in their business. 

That lack of clarity causes real problems. If you can’t define it, you can’t measure it. If you can’t measure it, you’re hiring and managing on gut feel. And in a startup, gut feel without structure can be expensive.

And there’s another issue = A/B/C player language isn’t useful in coaching.

You can’t sit someone down and say, “Well done, you’re a B player” and expect them to know what to do next.

That’s why I stopped using A/B/C labels years ago. Startups need something more precise, more actionable, and built for the pace and constraints of early-stage growth.

I saw the gap, I saw the pain it was causing, and I created the solution to help my clients (and everyone who's in the same boat!).

The Multiplier Matrix™ - Built for Startups on a Mission to Scale

The Multiplier Matrix™ gives you a clear lens for assessing impact - not just in hiring, but in developing and retaining your team.

It looks at two dimensions that matter most in startups:

1. 🤝 Collaboration & Ownership – Do they work well with others, and take responsibility for outcomes?

2. 🧰 Resourcefulness & Execution – Do they find solutions and deliver results?

Plot those on a matrix, and you get four types:

Spotting Each Type in the Wild

✖️ Multiplier

High on Collaboration and Ownership, high on Resourcefulness and Execution. They think like founders, see the bigger picture, lift others, and get exceptional results.

Example: A Head of Sales who not only builds and runs a repeatable playbook but also develops future leaders and shapes GTM strategy in lockstep with product.

➕ Adder

High on Collaboration and Ownership, but lower on Resourcefulness and Execution. They could be called “B players” - reliable, steady, supportive team members who are valuable, but won’t multiply impact. They’ll deliver in their role but won’t consistently elevate others or innovate beyond their lane.

➗ Divider

High on Resourcefulness and Execution, but low on Collaboration and healthy Ownership. They hit numbers and execute at a high level, but they do it in a way that creates silos, politics, and factions. They may be seen as “top performers” on paper, but over time they damage alignment and trust.

➖ Subtractor

Low across Collaboration, Ownership, Resourcefulness, and Execution. They drain energy, create drama, miss targets, and erode morale. If they are in leadership, your best people will leave. These are your C players — a costly drag on growth.

Why This Beats A/B/C Language

The beauty of the matrix is it gives you a shared vocabulary that works in hiring, coaching, and culture-building.

You can sit down with an Adder and say:

“You’re adding value, you’re solid in your role. But if you want to move into leadership or increase your impact, I need to see you taking more ownership of the wider business, being more resourceful in finding solutions, and delivering results beyond your current scope.”

You can speak to a Divider and say:

“You’re powerful, people respect you, but the way you’re using that influence is creating division. If you’ve got concerns, bring them to me first. We need to channel that strength toward the company vision, that’s the only way I can give you bigger opportunities.”

And you can use it in hiring, by spotting patterns in past behaviour.

Look for examples where a candidate -

• collaborated across functions,

• owned outcomes without waiting for instruction,

• found creative solutions with limited resources,

• and executed at pace.

Then test for those traits in your process. ✅ 

A Framework That Helps People Grow (and know what great looks like!)

Remember, every hire will either Add, Subtract, Divide, or Multiply your impact. 

When we’re talking about hiring managers, that impact gets amplified - for better or worse!

The goal isn’t to label people and leave it there. The power is in knowing where they are now, and coaching them to move up.

As Brent Holloway, Founder of Mastiff Software, put it:

“The multiplier matrix is a smart framework. I can reflect back and quickly internalise which of our team members were multipliers, and I think a system/process to identify more multipliers in the recruitment and interview process makes a lot of sense.”

Chelsey Langan, CRO at Think Warwick, nailed it too:

“You don’t just want great people. You want people who make others great. That’s the core of a Multiplier.”

And in the words of Warren Hammond, CRO at Volt.io:

“I love your scorecard because I love simple frameworks that allow people to break down complex problems. It provides a vocabulary and a perspective that helps drive better conversations.”

The Gain

If you only focus on the “gap” - how far someone is from your ideal hire or top performer - you’ll get stuck in frustration.

If you focus on the “gain” - what it would take to move them up the matrix - you’ll build a stronger, more aligned team over time.

The A/B/C player language is too vague to do that. The Multiplier Matrix™ gives you the map.

Want to know how Tick Talent can help you find some Multipliers?

If you're planning to hire for growth, or to strengthen your team, we might be able to help you get the edge you've been looking for.

Like the Sales Lead in our Toronto Series A client who helped them grow by 300% in her first 12 months, and just got promoted to Director of Sales.

Or the Head of Sales in our London seed stage client who helped them grow 120% in her first 9 months.

Or the privately-owned Barcelona company who, after steady growth over 25 years, brought in both a top-level Head of Sales and Head of Marketing to lead their global expansion.

If you're planning on hiring critical GTM roles, let's first understand what impact you're looking to achieve, align on the outcomes and success criteria, and see if there's a fit.

If you want to start by looking at your current team through the Multiplier Matrix lens, take the scorecard -

The Multiplier Matrix Scorecard

Keep in touch

Follow our podcast and content:

• What Makes You Tick

• TikTok

• LinkedIn

Thanks for having me! - Rich

With love and gratitude -

Connect on LinkedIn

If you want to learn more about working with me directly…

For B2B startups I serve as a Fractional GTM executive or advisor. Learn more about-

• My approach to client engagements

• My engagement models and pricing

• My success stories with other startups

• My customer reviews

When you’re ready, let’s connect to discuss your specific growth goals and challenges.

Apply to work with me here

Subscribe for weekly education, ideas, and frameworks

In this newsletter I share the exact tips, playbooks, and GTM multi-vitamins I’ve used to help 30+ B2B startups scale their revenue 150-590% YoY.

Subscribe now

Thanks for reading GTM for Startups by Jess! This post is public so feel free to share it.

Share