High Signal Podcasts Evidence ledger
Method
Browse
← Back to evidence

Evidence receipt / prediction

Published · transcript-backed

Jason Lemkin: prediction

1 Jan 2026 Lenny's Podcast We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr)

“" Even if it doesn't quite work. And I knew from this Delphi, this general agent that it would sort of work because going into annual, this general agent, this Digital Jason closed a 70K sponsorship on its own.”

— Jason Lemkin

Source trail

Everything needed to verify it.

Speaker
Jason Lemkin
Attribution
Verified speaker
Claim type
prediction
Recorded
1 Jan 2026
Publisher
Lenny's Podcast

Transcript context

…Yeah, that's true. So I am a two-time founder who started writing a blog, my God, in 2012 about all the mistakes I made after I sold my startup to Adobe. We started doing a couple meetups. You've done meetups. Before anyone did this stuff, we did a big meetup in 2015, thousands of people came. Then we do 10,000 people a year at SaaStr Annual. I've actually also invested almost 200 million dollars, almost 10X lifetime, only into founders from the community. But the reason I don't know is what I ... Folks that are connected to our content, I'm just passionate about helping other founders see mistakes and make less of them. So anyhow, we're a large community. I do invest, but it turned into a business. There was no revenue in the beginning. I'm sure there was no revenue, Lenny in the beginning. And ours was less intentional, but we do do eight figures of revenue a year and it's work. That sounds great to do eight figures, but there's a lot of costs, especially on the event side. The media side has almost no cost. And it's work. We have a hundred sponsors. And as you know ... You have sponsors, but there's a certain level where it becomes a lot of work. Getting two folks to sponsor your podcast with a couple emails, no work. If you wanted to have four Lenny podcast, it just scales. So we have built our own go-to market team over time, and I've lived the frustrations. Folks have followed it. And then, maybe I'm rambling a little bit. The interesting thing, the aha moment that happened to us is going into May of this year, we had one AI agent in production called Delphi that we both use for digital lending and Digital Jason. Really interesting learnings. And we went into our 10,000 person event this year with a seven-figure budget and eight-figure top line. And two folks on the sales team who were paid high end of market. I have many flaws, but paying well and being loyal are not one of them. And two of them just quit at the event. They just quit on site. And this is like the third time I've done this, like the eighth team I've built, and I turned to Amelia, our chief AI officer, and I said, "We're done with hiring humans in sales. We're done. We are going to push the limits with agents. We're going to put... " Even if it doesn't quite work. And I knew from this Delphi, this general agent that it would sort of work because going into annual, this general agent, this Digital Jason closed a 70K sponsorship on its own. So when I saw that a horizontal agent, not trained for sales, not trained for GTM could close one deal, they're like, "Let's deploy a couple of these apps. We have time. And I just can't pay a junior SDR $150,000 a year to quit. I just can't ... criticize me, but I just couldn't do it one more time. I just couldn't do it one more." And I actually think this isn't ... When I talk to CEOs at leading AI companies, they kind of don't want to do it either. They want to have the smallest sales teams they can as much for cultural reasons. I actually think this isn't ... When I talk to CEOs at leading AI companies, they kind of don't want to do it either. They want to have the smallest sales teams they can as much for cultural reasons. Even if Replit only goes from zero to 200, it could have been 220 with the smaller sales team. I think I'm just okay with it. So it's an enduring theme. But anyhow, so we pushed the limits. And now if you walk into SaaStr's office, it's kind of funny. We have 10 desks that used to be go-to market people. They're all just labeled with our agents, Repli for Replit, Quali for Qualified, Arti for Artisan. Agentforce needs a nickname. Maybe we can make one up with Salesforce. There's Amelia's corner office at one end. I'm in the back of the office and it's just agents. It's the quietest office. And net-net, Lenny, it's about, here's the Meta learning for when we're recording this. The net productivity is about the same. It's not better, it's not worse, but it's so much more efficient and it scales because software scales. And we can talk about what we've learned. I think it's important that it takes time to train these agents. They don't work out of the box. But when you dial them in, when you take your best person or your best script and you train an agent with your best person and best script, that agent can start to become a version of your best salesperson, your best person. And that's what we've learned and how to perfect it. And I just think because ... and criticize me, you or anyone watching or listening, maybe it's not cool. I didn't want to hire my 28th rep that was going to quit, but I just couldn't do it one more time in the age of AI. I'm like, "It's time to go to the bleeding edge and just see what we can push the limits here."…

Stored transcript either side of the excerpt. The highlighted words are the published quote; the surrounding text is unedited source, never generated.

Search evidence