Jason M Lemkin
We replaced our sales team with 20 AI agents—here’s what happened, covering B2B products, startup building, and team leadership.
Episode
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr)
Summary
Jason Lemkin, founder of SaaStr, delivers a detailed playbook for B2B sales — covering when to hire your first salesperson, who specifically to hire, and why the vast majority of sales leaders today are burned out. The episode includes his argument that founders must close the first 10 customers personally, why you must hire two reps before a VP of sales, and why the "sell me this pen" demo assignment is still the only reliable hiring test.
Key Takeaways
Close your first 10 customers yourself before hiring a salesperson — even if you hate sales, you know your product and their problems better than any hired rep will at that stage.
Hire two sales reps before a VP of sales. The VP's job is to take you from rep 3 to 300 — hiring a VP first, hoping they'll find PMF and close deals simultaneously, has near-100% failure rate.
Your first reps must be people you would buy your own product from — not people with impressive logos on their LinkedIn. A quirky rep who loves your product will outperform a polished rep from a brand-name company.
Ask VP of sales candidates: "What do you want to do in your first two weeks?" If you don't hear "meet customers and join calls," exit the interview.
Require all sales candidates to demo your product back to you — 98% won't even watch the explainer video on your website before applying. The one who does the work is the person to hire.
Notable Quotes
“I think it's great. I think it's an evergreen topic, but I think there's remains a consistent set of confusion, fears around how to build a sales team, and it's evergreen. The tools change and the pace has changed, but the issues, I love to dig into them because we keep making the same mistakes as founders and executives again and again and again.”
“The most important thing though I've found is however you get those first 10, 15, 20 customers, be honest, be honest, and if you've talked to them as a founder and you know that they need a sales type motion, they need effort to deploy it, they have questions about security, they have questions about competition, they have onboarding requirements, and you say, "Hey, I don't like sales, so I'm going to do a PLG motion," you'll fail.”
“And sometimes even the founders get mad at me for doing this, because sometimes, the candidate bails. But I'm like, "I know you're mad at me today, but it is your fault. A hundred percent your fault if any of your hires fail. Don't blame them. And I'm guilty of this. I get upset when people start and they don't give it their all or they don't do it. I mean, what if you hired someone for your podcast and they decided, "You know what? I don't want to do the podcast this week. I'm tired. I'll do it..." You're so mad at them, but you should've seen it during the hiring process. Right?”