Is it the sales rep, or is it you? A founder's diagnostic for failing sales hires
The variables you can control, leading indicators of success, and decisions with conviction
Hi friends - Happy Father’s Day to all the dad’s out there! We’re in New Orleans this weekend celebrating my baby daddy’s first Father’s Day. Luca is almost ONE if you can believe it.
This week’s article was inspired by several recent conversations with founders. It’s a conversation I’ve had many times over the past four years.
For all of you who have experienced sales hiring failures, or who are unsure about your current bench - this one is for you. Hope it helps.
Is it the sales rep, or is it you? A founder’s diagnostic for failing sales hires
One of the most common reasons founders bring me in — or consider bringing me in — is that they’re desperate to get out of founder-led sales and they can’t, because the sales hires they’ve already made haven’t worked.
They’re either sitting with a rep who isn’t hitting their numbers and don’t know whether to keep investing or cut bait, or they’ve already let one or two people go and want a second set of eyes before they try again.
It’s the same underlying question every time:
Am I the problem, or is it them?
The honest answer, most of the time, is: at least part of the problem is definitely on you – the founder.
The infrastructure around the rep was too noisy to isolate the variable that mattered — their individual performance – and until you do your part, we often don’t have enough clarity to say with certainty whether the rep would or wouldn’t have been successful.
Many founders start wondering if salespeople just don’t work at their stage. They absolutely can – in the right conditions.
You’re running a noisy experiment
Before you can fairly evaluate a sales rep’s performance, you have to remove the variables that have nothing to do with the individual. I love to refer to this as “removing the excuses”.
If your sales motion isn’t documented anywhere, if your ICP is vague (looking at you “we sell to enterprises”), if “what good looks like” was never written down, and if there’s no weekly rhythm for surfacing problems — the rep is operating inside your chaos. Their performance reflects both their skill and your environment, blended together. You can’t pull them apart.
When I dig in with founders, the conversation almost always lands in the same place: maybe the rep was the problem, but the setup was so unfair that we can’t actually tell with certainty. So we rebuild the environment, hire again, and find out a lot faster.
That’s the reframe. Your job is to remove every excuse the rep could legitimately make before evaluating a sales hire. Once they have none, what you see is what you’ve got.
The four controllables every founder owns
The variables you control — the things the rep can’t fix for themselves — fall into four buckets. Get all four in place and you’ve removed the founder-side excuses. What’s left is the rep’s performance.
1. Minimum viable sales enablement
The artifacts your rep needs on day one: a documented sales process with deal stages, a real pitch deck, demo script, discovery framework, objection handling, pricing rationale, contracts or order forms, and a CRM that isn’t a graveyard. None of it has to be perfect — it just has to exist.
The trap I see most often: founders hire a rep expecting the rep to build all of this for them – or somehow operate without it. Some will tell you they’re up for the build. A small handful of unicorns can actually pull it off (more on them at the end). But most sales reps have never had to set up a CRM, define an ICP, or build a playbook — they were trained to learn the plays that already existed – and run them. Asking them to stand up your entire sales motion while building a pipeline is the single most common reason first sales hires fail.
If you’re starting from scratch, this pre-hire checklist is your map — aim to have at least 80% of it built before your rep’s start date. And document the playbook, even in rough form, so your rep isn’t piecing your sales motion together from Slack threads.
2. A tiered ICP — and better yet, a named list of accounts
Building on #1: a documented ICP is the floor, not the ceiling. Telling a new rep “we can sell to any company that fits this criteria” is essentially telling them to go boil the ocean. They’ll spend their first month in analysis paralysis, and most of that effort won’t show up as pipeline.
The version that actually works: give them a tiered ICP or better yet – a named list of look-alike accounts modeled on your best closed-won customers. Small enough that they can work it surgically — go deep on each one, map the buying committee, find the right entry point — instead of spraying outreach across five thousand companies that technically fit your ICP definition.
A rep doesn’t need to be told who to target in the abstract. They need to be told “these are the 50 or 100 companies that look most like the ones we already won. Start there.” Pair that with defined buyer personas inside those accounts and they can hit the ground selling, not researching.
3. Expectations clear enough that failure is visible
This is where I see the most damage. Founders hire reps with mandates like “hit your quota” or “build pipeline” and then can’t tell at week six whether things are on track. By the time the lagging numbers tell a clear story (closed won deals), you’ve burned six months and a paycheck.
The fix is to define both lagging and leading indicators of success before the rep starts. What does week 4 look like? Week 8? Week 12? How many meetings should they be booking, how many opportunities should be in pipeline, what’s the activity floor? Write it down, share it with the rep, and check those numbers weekly. Leading indicators give you 90+ days of forward visibility. Quota attainment will only tell you what already happened – activity, pipeline coverage – that tells you what is highly probable to happen.
This is also the moment to make sure your comp plan math actually maths. If the rep can’t back into what they’ll earn at quota — base, OTE, commission rate, ramp structure — OR – if the quota doesn’t feel remotely realistic – it’s hard for them to feel incentivized to win.
4. An operational cadence — and the infrastructure to support it
There are two parts to this one: the rhythm and the infrastructure that makes the rhythm useful.
The rhythm. Weekly pipeline reviews, 1:1s, deal reviews, and sometimes stand-ups for the broader team. The weekly pipeline review is the load-bearing meeting — where you catch deal slippage, hear the objections killing deals, spot whether the rep is working the right accounts, and reset in real time.
The infrastructure. Record every sales call and log every email in your CRM. Not for surveillance — for visibility and analysis. Without it, your only feedback loop on your rep’s performance is what they tell you, filtered through their interpretation of what happened on the call.
With recorded calls and logged emails, you (and your favorite AI) can review what’s actually happening in deals without sitting in every meeting or reading every thread. AI tools can analyze call transcriptions, summarize them, surface objection patterns across a week’s worth of conversations, and flag where a rep is struggling at specific stages of your process.
That’s the difference between coaching from vibes and coaching from data. And it’s especially critical at startup speed, where you don’t have time to listen to every call or read every email yourself. Check out: Why RevOps is your secret weapon (for both humans and AI).
This is easier than it’s ever been
Building all of this — the enablement, the named account list, the expectations doc, the cadence and infrastructure — sounds like a lot of work. It is. But it’s never been easier to do than it is today.
Claude, ChatGPT, or whatever AI you prefer — paired with talk-to-text — turns a “write the sales playbook” project into a few hours of dictation that gets organized into a usable document. Same goes for your ICP, your personas, your weekly review agenda. Drop your call transcripts or HubSpot pipeline data into the same tools and a simple prompt will surface patterns across them in seconds: which objections are recurring, which deals are stalled, which reps are struggling at which stages.
What hasn’t changed: you still have to spend the time to build the infrastructure, and you have to understand what you’re inspecting.
But, I was able to sell without any of this?
The objection I always get when I walk founders through this framework:
“Well, I was able to sell without all of this. Why can’t they?”
Right — and you’re a unicorn. As the founder, you’ve got context, conviction, and credibility that took years to build and lives almost entirely in your head. Very few sales reps can replicate what you’ve done without an explicit playbook and clear instructions, because they don’t have what you have.
Not to mention…you have added incentives they don’t. Your reputation, your responsibility to investors, your personal equity in the company.
Occasionally you do find a sales unicorn. They exist – the people who can succeed even in chaos. But they’re rare enough that building a hiring strategy around finding one is closer to gambling than strategy. The math doesn’t work in your favor.
And here’s the other part founders miss: even when you do land a unicorn, the lack of infrastructure eventually pushes them out. They get exhausted carrying it all themselves. Their close rates underperform what they could be earning at a company with a defined process and an easier path to commission. They leave for the place that did the work — where their earnings are easier or better.
So even if you somehow find the unicorn, designing your environment around their ability to thrive in chaos is a losing strategy. Build the infrastructure that works for the majority of reps who need it — and the unicorns will perform even better on top of it.
Your diagnostic this week
If you’re sitting with a sales hire that isn’t working — or about to make your next one — run yourself through these questions honestly:
If a brand-new rep walked in tomorrow, what percentage of the pre-hire checklist is actually in place? Be ruthless with yourself.
Could that same rep tell you, in their own words, who your ICP is and which named accounts to chase first?
Do they know what “good” looks like at week 4, week 8, week 12 — by leading indicators, not just closed-won?
Is there a weekly pipeline report and review where you’d catch slippage in real time, not at the end of the quarter?
If the answer to any of those is no, the rep isn’t your only variable yet. The environment needs to control your experiment. Fix what you own, manage reps to leading indicators, and make the hard calls as fast as possible – with much more conviction.
With love and gratitude -
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