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Hire the Person
You'd Buy From

Jason Lemkin
Founder, SaaStr · Fmr. CEO & co-founder EchoSign ($100M ARR, sold to Adobe)
JAN 1 2026
The Premise

Founders Close
the First 10

FOUNDERFIRST 10SIGNAL
"95 times out of 100, you've got to find a way to close the first 10 customers yourself, even if you hate sales."
  • Customers love talking to the CEO; founders are "A+ middlers" once someone is in the spider web
  • The first 10–20 customers tell you your motion; PLG, sales-led, or hybrid, be honest about which one you actually are
  • Producty founders who exit sales because it's "icky" fail; one $5M co. fired its sales team and shrank back to $1M
  • You can defer sales like Canva (well past $500M revenue) or start hybrid like Slack, but you cannot pretend
Framework

When and How to Hire

20% TIMEHIRE 2 REPSTHEN VP OF SALES
20%
of your time on sales ⇒ hire
2
reps, never one; you need an A/B
30
interviews to find the right one
  • Hire two, not one; without a second, you have no way to tell if the problem is the rep or the product
  • Wait for two reps to hit quota BEFORE hiring a VP of sales; earlier is close to a 100% failure rate
  • The rep costs $2M of your $4M in eight months if you hire the wrong VP first
  • Founders spend 20% on sales and 20% on recruiting; nothing else really matters as CEO
The cheat codeHire someone you would buy your own product from. If you wouldn't buy from them, no logo on their LinkedIn will save you.
The Interview

The 30-Rep Funnel

  • 20 break your brain: no prep, didn't visit your website, don't know your product
  • 8 are "okay": you'd hire them if you got tired
  • 1–2 are magicians: they explain your product back to you in a way you actually believe
  • The tell: ask if they watched the explainer video. Most sales reps haven't, even by the fifth interview
Sell me this app

The Glengarry test, still the best. Give them 30 min to two hours to prepare. Whoever can't sell your own product back to you cannot sell it to a stranger.

Pirates and romantics

Not the process person from Snowflake. The quirky one who fell in love with your feature-poor product. Give them the precious early leads.

Playbook

Building the Sales Team

  • Close the first 10–20 customers yourself, even if you hate sales; customers love talking to the CEO
  • The first reps need a couple of years of experience, a similar deal size, and enough maturity to trust with a precious lead
  • Early reps must be product gurus; later hires can't be, or you can't scale
  • When the VP of sales starts, they should be in 20–30 deal hours a week; if they're not in the deal, they don't know the deal
The Benioff ruleMarc Benioff still flies to Davos, sits at the top of the same staircase, meets prospects in person all day at $30B revenue. If that's efficient for him, it's efficient for your VP of sales too.
Contrarian

Sales-Team Myths Jason Rejects

✗Hire one great rep firstINSTEAD →✓ Never hire one. Hire two. Otherwise you can't tell if the problem is the rep or the product.
✗Hire the VP of sales to build the teamINSTEAD →✓ Wait until two reps are hitting quota. Earlier is a Hail Mary; two million of your four-million round burns while they figure it out.
✗Hire from Twilio and CloudFlare, they know salesINSTEAD →✓ Hire the person you would buy from. Logos on a LinkedIn do not survive contact with your leads.
✗Fire sales, go PLG, save moneyINSTEAD →✓ One SaaS co. did exactly that at $5M, growing 100%. They shrank to $1M in twenty months. Being honest about your motion beats hating the motion.
Based on Jason M. Lemkin's episode on Lenny's Podcast. All ideas on this page are from the episode.Watch on YouTubeFollow @jasonlk on X
GO DEEPER IN THE EPISODE
01:27 Framing the whole conversation around building a sales team06:09 Does every B2B company need a sales team?09:00 Being honest about the motion you actually have10:28 When PLG founders finally hire salespeople11:06 Not IF you need a sales team, WHEN18:57 Founders as A+ middlers; close the first 10 yourself22:45 The 20% rule: when to hire and why always two reps26:43 The cheat code: hire the person you would buy from30:06 Two reps hitting quota BEFORE a VP of sales35:17 What to look for in the first reps and the VP39:54 "Sell me this app" and the interview reality46:53 The Benioff visit: why sales leaders still fly to customers
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