Founder of SaaStr, B2B SaaS investor
Jason Lemkin runs SaaStr and its annual AI event, and an earlier company of his was acquired by Adobe. On 20VC he keeps predicting that companies will choose AI tokens over humans. He expects QA departments and the marginal roles in customer success to go first, and says SaaStr has already made that choice.
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Retention
Most SaaS churn is not a product problem. It is a customer problem: you sold to the wrong ICP.
I have passed on every single company that had, for their segment, abnormally high churn. I've gone back to so many founders that were at a million with 78% churn, I'm like, you have something, but it ain't SaaS. It's not SaaS.
Jason Lemkin
says churn that is abnormal for your segment almost always means you sold to the wrong ideal customer profile. The product can be fine and the buyer wrong, so the fix is positioning and go-to-market, not a quarter of engineering.
says the customer hired you for a job, then their context changed and the job moved on, so the switch that brought them in reversed. The fix is to interview the churned and find the struggling moment, not to re-segment.
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Hire two sales reps initially for A/B testing, not one
Building a sales team - hiring two reps allows comparison and reduces risk of misjudging individual performance
VP of Sales should only be hired after two reps are consistently hitting quota
Hiring a VP before establishing a repeatable sales process is a common and costly mistake
Building a world-class sales org | Jason Lemkin (SaaStr) 18:59
Interview 30 sales reps before making early sales hires
Focus on individuals you would buy from, prioritizing those who genuinely love the product
AI agents are not plug-and-play - they require significant training and ongoing oversight
A 'Chief AI Officer' or similar role is needed to manage, train, and iterate on AI agents for effectiveness
We replaced our sales team with 20 AI agents—here's what happened next | Jason Lemkin (SaaStr)
In the B2B sales cycle, the core job is problem-solving, not selling
Understanding customer needs and providing value creates better outcomes than traditional sales approaches
