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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai, Sales
The GTM Stack Anthropic Uses From Its Head of Industries: Surprisingly Familiar Names. Used In New Ways.
You’d assume Anthropic, of all companies, would be running on some self-grown, cutting-edge AI-native sales platform. Maybe a Salesforce killer they built themselves. Maybe Claude baked into the protocol layer of every workflow. They aren’t. At least not yet. Claude is baked into their stage, it’s the substrate. But it’s used to connect to the…
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
A Deep Dive With the Replit Team on Our Agents: 10K, QBee, the AGI-ish Bloomberg Beta Email, and Programming in English (For Real)
The Replit team came out in force to SaaStr AI 2026 (from the CEO to the CRO and the President!). They also in an unguarded moment interviewed me on stage and off stage about how we’re actually running SaaStr AI with our agents. The real, unglamorous, in-the-weeds operational reality of running a B2B media +…
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Blog Posts, Career Growth & Advice, Growth, Q&A, Sales, Sales
Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make?
Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make? Let me just summarize my #1 observation here: the top mistake first-time sales managers make is recruiting. In that — they can’t do it. They can’t recruit great reps. They can recruit some mediocre ones, but that’s about it. It is incredibly hard to figure…
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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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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. We went off on...
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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