Jason M Lemkin
Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs.
Launch & Go-to-Market Skills
Founders should hire their first salesperson once they have closed ten unaffiliated customers and find that sales activities consume more than twenty percent of their weekly schedule.
"I think as soon as you've got those 10 customers and more than 20% of your time is booked up with customers, you need leverage. You need leverage."
Hiring two sales representatives simultaneously allows founders to distinguish between individual performance issues and fundamental flaws in the sales process.
"So you need to hire one rep and you've got to hire two because otherwise, there's no A-B test. You have to A-B test humans."
Overlay: Zero-to-One / Founder Skills
Successful founder-led sales require transitioning from technical problem-solving to a direct request for a financial commitment and clear next steps.
"Work up your courage, and find how to ask for next steps and money. What would it take, Lenny? How can we get going on Riverside? What would it take?"