Lenny's PodcastBuilding a world-class sales org | Jason Lemkin (SaaStr)
At a glance
WHAT IT’S REALLY ABOUT
Jason Lemkin’s playbook for building and scaling B2B sales teams
- Jason Lemkin lays out a practical, often counterintuitive blueprint for when and how to build a B2B sales organization, starting with founders closing the first 10 customers themselves. He explains why your first two sales hires must be people you’d personally buy from, why you should delay hiring a VP of Sales until at least two reps are reliably hitting quota, and how to structure compensation so reps are accretive rather than a cash drain. The conversation dives into the critical (and tense) relationship between product and sales—how product leaders should engage in sales cycles, handle feature requests, and think about free trials and pricing. Jason also touches on event strategy, arguing that small, high‑quality customer gatherings are often more valuable than mid‑tier conferences, and urges product leaders to make this “the year of the customer.”
IDEAS WORTH REMEMBERING
5 ideasFounders must close the first ~10 customers and be honest about their motion.
If your earliest unaffiliated customers need hand-holding, security reviews, and deployment help, you do not have a pure PLG motion—ignoring that and forcing self‑serve will likely kill the business. Founders, even if they dislike “sales,” are usually excellent in the middle of deals and must learn to ask for the next step.
Hire two AEs early, not one—and only if you’d buy from them.
You need an A/B test on humans, which means hiring two initial reps and comparing their performance and style. Ignore shiny logos on resumes and prioritize reps who deeply understand your product and can explain and sell it in a way that convinces you personally; early leads are too precious to give to someone you wouldn’t buy from.
Delay the VP of Sales until two reps are reliably hitting quota.
A VP of Sales’ real job is taking you from roughly 3 to 300 reps, not finding product‑market fit and being your first closer. Hiring that role before a basic sales motion is working almost always fails and burns cash; when you do hire them, they should spend 20–30 hours a week in deals and be willing to carry a quota.
Structure sales comp so reps can win early, then become clearly accretive.
Pay roughly market OTE (often 50/50 base/variable), let new reps keep 100% of what they close for their first quarter to ramp, and then aim for them to close 3–5x their OTE annually depending on deal size. Don’t obsess over squeezing OTE down by 10–20k; the real question is whether they can consistently sell multiples of what they take home.
Make product a core weapon in big deals and formalize sales’ roadmap influence.
Great heads of product deeply engage in sales, especially large or complex deals, where their product fluency and authority can make or break contracts. To avoid chaos, give sales a fixed quarterly “budget” of roadmap influence (e.g., 10% of capacity) and force them to prioritize, instead of reacting ad‑hoc to every big prospect request.
WORDS WORTH SAVING
5 quotesWe’re not really selling in B2B. We’re solving problems.
— Jason Lemkin
Those first couple reps have to be people you would buy your own product from.
— Jason Lemkin
If you hire a VP of Sales before two reps are hitting quota, there’s approaching a 100% chance of failure.
— Jason Lemkin
Every time you rip a customer off, you lose compounding.
— Jason Lemkin
Make this the year of the customer. Ship three great things this year—great, not good.
— Jason Lemkin
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