Hi there - This is some of my best work if I do say so myself.

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! 😉

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.

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.

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. 

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

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:

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

Ask for copies of all sales assets:

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

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.

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

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.

Immediate priorities - Get crystal clear on:

Sales intelligence - Learn about:

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.

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:

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

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

Now it's time to really dig in:

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:

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

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:

Set up one-on-ones with:

Ask them:

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

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.

Go through every open opportunity in the CRM:

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

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

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.

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

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:

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:

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

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

Tech stack audit:

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

Sales assets audit:

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.

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.

Start executing on the strategy you built in week four:

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. 

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.

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

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

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.

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

Pay attention to what's working:

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

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:

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.

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:

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.

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:

Setting this expectation now prevents frustration and misalignment later.

Your work doesn't stop at week six. Here's what you need to know about the months ahead.

This should remain a standing meeting. Use it to continuously ask questions, provide updates, review deals, and iterate on what you're doing.

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:

This ongoing cadence is the only way you're going to collaboratively move past challenges and stay aligned.

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.

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. 

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With love and gratitude,