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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
The AI Board Member: Should Yours Should “Chair” the Next Meeting? At Least Conceptually
I just got out of a 3 hour board meeting where the first 2 hours were an almost total waste of time. 5 busy executives reviewed 30 slides that no one really had read ahead of time. And then a bunch of VCs made generic comments that sounded directionally correct but in the end were…
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Blog Posts
Jason’s Takes on This Week’s 20VC: The Toggle Is a Permission Grant, The Blame Test Decides the Deal, and Why Five Years of Price Increases Is a Countdown
The version of this week’s episode I’d give a founder over coffee, including the part where an agent rewrote my core algorithm and I found out from a merge conflict. Harry, Rory and I covered Jensen’s open-weights letter, the OpenAI model that escaped its sandbox, Etched at $10B, Alphabet’s first negative free cash flow quarter,…
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
The #1 Most Important Thing to Understand About AI SDRs: They Can’t Figure It Out For You. That’s Still Your Job. For Now, At Least.
10x Times Zero Is Still Zero: The #1 Thing to Understand About AI SDRs AI SDR and AI GTM agents are everywhere now. Every vendor promises they’ll 10x your pipeline. And they do work. They really do. We have the data 😉 From Agentforce to Artisan to Qualified to Monaco and more, a well-trained AI…
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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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