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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
When the Agents Pick: The B2B Categories AI Agents Don’t Need
When the Agents Pick: Why Marketo, Outreach, Salesloft and Atlassian Aren’t Built for AI Agents The other day we built an Agentic API grader. The setup was simple. I had Claude, OpenAI, and Gemini take the top 120 APIs together and grade which ones they thought were the best for agents to use. Stripe came…
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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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Blog Posts, Q&A, Sales
Dear SaaStr: What’s Really Changed in GTM in 2026?
Dear SaaStr: I run revenue at a B2B company doing about $40M ARR. My playbook is basically the one I built in 2021 and 2022, and it’s working worse every quarter. What’s actually changed in go-to-market, and what should I be doing differently? The ICONIQ State of Go-to-Market 2026 report is some of the best…
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Aaron Levie, CEO and Co-Founder of Box
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Eric Yuan, CEO & Co-Founder of Zoom
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Lew Cirne, CEO of NewRelic
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Scott Dorsey, CEO of ExactTarget
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Aaron Levie, CEO and Co-Founder of Box
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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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