Hire the Deputy, Not the VP
Hire two gritty early-stage sellers from an analogous company, not a professionally rich VP.
- Difficulty
- Advanced
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 94%
Kazanjy's counterintuitive hiring rule: after you have personally closed 10-30 customers, do not hire a head of sales. Hire two gritty early-stage individual contributors who sold a similar persona at a similar price point at a company that was, at the time, roughly as immature as yours. A VP who scaled a Datadog or a Figma has not carried a bag in years, has no collateral-free muscle memory, and — as Jason Lemkin has pointed out — is professionally rich and has little reason to grind at your crappy little startup.
Origin
Kazanjy's framework from Founding Sales and his 'founder-led selling' talk; he credits Jason Lemkin for the pointed observation about why a been-there-done-that VP of Sales wouldn't want to do it again.
Core principles
- 01Early-stage selling takes early-stage sellers — the collateral will not be buttoned up with a bow around it.
- 02Match on persona sold and average selling price, not on brand-name logo.
- 03Recency of the company's stage matters more than the company's current prestige: an AE who joined Greenhouse last year learned a mature motion, not a founding one.
- 04Two hires, not one and not four: one gives you no signal, four is too many to manage.
- 05Great senior sellers will underwrite you, not the other way round — you must show them proof.
How to run it
- 1
Clear the prerequisite
Reach minimum sufficiency yourself first: 10, 20, or 30 customers closed personally at arms length, with a reliable win rate. Only this earns you the right to hire.
Watch out Revenue trades inside an accelerator, or friendly buyers, do not count as an existence proof.
- 2
Identify the analogous sales orgs
Find companies that sell to the same persona at a similar average selling price. If you sell recruiting software, look at Lever and Greenhouse. If you sell a design tool, look at Figma.
Pro tip The persona and the price point are what transfer; the product category matters less.
- 3
Target the early-tenure cohort, not the current stars
Within those orgs, find sellers who were there two or three years ago when the motion was still being built — people who sold without polished decks, scripts, or a mature playbook. Avoid AEs who joined recently and only ever ran a mature machine.
Pro tip A sales manager who is not far removed from personally selling can also work — someone still willing to roll up her sleeves.
Watch out Hiring the current-day AE from a great sales org imports a dependency on collateral you don't have.
- 4
Hire two, hand them the packaged motion
Bring on two (at most three) sellers simultaneously and give them the artifacts: the slide deck, the written discovery questions, the demo script. Two lets you distinguish a bad motion from a bad hire.
Watch out If the collateral is not present, no one will be successful — and you will misattribute the failure to the hires.
- 5
Earn the senior leader with proof
Only after those two reps are succeeding do you recruit the experienced early-stage head of sales — and you close her with evidence: your own 25% win rate, plus two reps at 20% win rates each closing $50k of bookings a month. The ask becomes 'all I need you to do is scale it up.'
Pro tip Assemble that evidence pack before the first conversation with a senior candidate; it is the pitch.
Watch out A strong sales leader will demand proof of product-market fit. Without it, either she declines, or she accepts and both of you lose.
In the wild
Kazanjy's friend Troy runs Guide, a recruiting software company selling into recruiting organisations. The right first sellers are not stars from today's Greenhouse — they are the people who were early at Lever or Greenhouse, selling the same recruiting persona at a similar price point before the playbook was written.
→ The profile screens for grit and collateral-independence rather than for brand-name pedigree.
A candidate like Marissa Fuhrer (enterprise at Figma, previously a long-time Dropbox seller) will look at a startup and demand proof that the product fits the market before betting her career. The founder answers with numbers: a 25% personal win rate, two sellers at 20% win rates, each closing $50k of bookings a month.
→ The proof converts a skeptical, in-demand leader into a yes: all I need you to do is scale it up.
Common mistakes
Hiring a VP of Sales as the first sales hire
A manager-of-managers hasn't been selling for a hot second. They arrive expecting a machine to optimise, find a blank page instead, and fail — which is why first-VP-of-Sales tenure is famously short.
Hiring only one seller
With a single hire, a failure is ambiguous: you cannot tell whether the motion doesn't transfer or the individual is wrong. Two gives you a control.
Hiring four or more at once
Too many to manage and coach at founding stage. Coaching bandwidth, not headcount, is the binding constraint on making a new seller successful.
Is it for you?
Best for
Seed to Series A B2B founders who have personally closed 10-30 customers and are making their first sales hires.
Not ideal for
Companies past product-market fit with a mature, documented motion, where a scaling leader genuinely is the right next hire.
From the transcript
“the reason why I advocate for folks to like hire a couple of sellers or a couple of AEs to start is because again, you…”
“early-stage selling takes like early-stage sellers or people who've been there because you're not going to have all the collateral, like slides and scripts and…”
“the early-stage sellers that he would be interested in would probably be like early people at like Lever or Greenhouse, right? Who sell to the…”
“in addition to having a 25% win rate with me, I have these two sellers right here and they both have 20% win rates and…”
“You you got to you have to get to that minimum sufficiency of”
From the episode
Founder-led sales
Pete Kazanjy (Founding Sales, Atrium)