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Jason’s Takes on This Week’s 20VC: Anthropic’s S-1, Microsoft’s 27% Buyout, and My 100-Day Rule
What founders should do differently after Anthropic’s S-1, Microsoft’s buyout offer, Cloudflare’s 20% cut, and a Qwen model trying to reach a server in Beijing Every Thursday, Harry, Rory and I go through the week’s news on 20VC x SaaStr. Here are the 10 things from this week’s episode I’d want a founder to act…
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Our Core Vendor Was Down for 24 Hours. Our AI Agent Replaced Them Before They Came Back Up.
The other day one of the core products we run SaaStr AI on went down the entire day. Not degraded. Down. For the entire day. Every screen in the app showed a large “INTERNAL ERROR.” The API returned the same thing, which meant every agent workflow that touched this product stopped cold. And we run…
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Blog Posts, Sales
If Your CRO, CCO or CPO Doesn’t Meet With Customers Their First Week On The Job … Move On. Apologize, But Let Them Go.
"A VP Sales, Product, Customer Success, all of them … have to meet customers their first week. They have to. Or don't hire them. You'll be surprised how many folks want to be managers, but not meet customers or do a lot of the work themselves. So ask them. Ask them what… pic.twitter.com/QyicrUVmks — Jason…
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7+ Tips On How To Build Your First Sales Team. When You Have Zero Experience Building One.
Dear SaaStr: How do you structure a sales team ... when you’ve got zero experience doing sales? Well, first go get some experience with sales. 🙂 At least, close the first 10 customers yourself. If you don’t, you’ll never have any idea how to do it. And the odds your...
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.
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