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20VC x SaaStr: The Token ROI Crisis Comes for Everyone, Anthropic Wants Chinese Open Source Banned, and Microsoft Has Its Worst Month Since 2000
With Harry Stebbings, Jason Lemkin, and Rory O’Driscoll We recorded this on the last day of June, and one theme ran through almost every story: Companies quintupled their token spend in the first half of the year. Almost nobody can point to the revenue lift that justified it. That’s the real state of the AI…
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Vercel Took a 10-Person SDR Team Down to 1. The Whole Thing Costs $5,000 a Year. With Vercel’s COO Jeanne DeWitt Grosser.
Vercel’s COO Jeanne DeWitt Grosser ran go-to-market at Google and Stripe for roughly a decade each before joining Vercel. Six weeks into the job, in June 2025, she stood up a go-to-market engineering team with one mandate: bring agents to everything in GTM. That was before “GTM engineering” was a phrase anyone used. Ten months…
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Blog Posts, Customer Success, Marketing, Q&A
Dear SaaStr: Does It Make Sense to Have Post-Sales Functions Report into Sales?
Dear SaaStr: Does It Make Sense to Have Post-Sales Functions Report into Sales? In many ways, this is the question of the day. So many SaaS companies, faced with slower growth, are moving CS in particular in to the sales department, trying to get more growth from the base. Is it a good idea though?…
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"SaaStr is the largest community of people who like enterprise software on the planet. It’s a great community of people trying to build companies and learn from one another. It’s pretty amazing to see."
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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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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