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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai, Sales
Sales Used to Be the Engine. For the AI Leaders, It’s Often More the Caboose.
There’s an argument going around right now that sales isn’t as important as it used to be. Still important. Just not as much as it once was. Bear with me here. It’s not an argument I agree with. But I can’t argue with the logic. The point is this: the world has bifurcated. And what…
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Why It’s So Hard for Older B2B Leaders to Compete in AI: Your Customers Can Do A Lot in Claude for $20-$200/Month. And You’re Paying $1.00 Per API Call For the Good Stuff.
I was recently catching up with the CEO of a B2B leader who was proud their AI cost was now just pennies per customer. And look, I get the impulse — that’s real engineering discipline. But to me, it also means you just aren’t competitive. Anything genuinely great in AI + B2B generally costs far,…
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Building AI Agents That Actually Work: Lessons from Jason Lemkin, Jeanne DeWitt Grosser (Vercel), Amelia Lerutte & Amjad Masad (Replit)
The half-day that kicked off SaaStr AI Annual 2026 was the most concrete look we’ve put on a stage at what running a company on AI agents actually looks like. Not the hype version. The real version, with the costs, the bugs, the drift, and the wins. Four sessions, four very different angles: a hands-on…
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Schmoozing Is Dead, Agents Are Hitting 120% of Humans, and Growth Is the Only Thing That Matters: 10 Things From the Closing Q&A at SaaStr AI Annual 2026
We just wrapped SaaStr AI Annual 2026, and the closing Q&A on Day 3 ended up being one of the most engaged of the whole gathering. No script, no prepared deck, just an hour-and-a-half of questions from the audience on the topics most on their mind....
Dear SaaStr: What Was the Toughest Rejection You Ever Had in Sales?
Dear SaaStr: What Was the Toughest Rejection You Ever Had in Sales? The hardest rejection I’ve had in sales was around renewals. Especially ones I thought we really had earned. But still lost. In particular, in the early days of EchoSign / Adobe Sign, we had a...
Dear SaaStr: What Is the Playbook for a Successful Customer Success Team?
Dear SaaStr: What Is the Playbook for a Successful Customer Success Team? A good playbook for customer success is all about driving retention, expansion, and customer happiness while making it scalable: Hire Truly Product-Savvy Customer Success Managers at First Focus...
AI at Scale: 8 Learnings from monday.com Co-Founder and Co-Ceo Eran Zinman
monday.com Co-CEO and Co-Founder Eran Zinman recently sat down with SaaStr CEO and Founder Jason Lemkin to share his insights on their journey, including how they’ve leveraged AI, maintained growth, and expanded into multiple product lines.
The 2025 SaaS Vibe Check: What Founders Need to Know Right Now with SaaStr CEO and Founder Jason Lemkin
SaaStr CEO and Founder Jason Lemkin did a vibe check into the state of SaaS, AI, venture funding, and the rollercoaster of building a business in 2025.
Dear SaaStr: Can an Entrepreneur Back Out of a Signed Term Sheet Without Damaging Their Reputation?
Dear SaaStr: Can an entrepreneur back out of a signed term sheet without damaging their reputation? In my experience — Yes, probably. As a founder, you can back out of a term sheet if something is off, or even if you just get another offer you prefer. There is a lot...
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