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Blog Posts, Compensation, Hiring, Q&A, Sales, Scale
Dear SaaStr: What Sales Comp Plan Should I Use For Our Very First Sales Rep?
Dear SaaStr: What Sales Comp Plan Should I Use For Our Very First Sales Rep? At the end of the day you have to solve for two things: A plan that gives the reps a living, fair wage; and A plan that you know and feel is accretive to the company. Sales reps have to…
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Blog Posts
20VC x SaaStr: Anthropic’s S-1 Shows $16.3B in First-Half Revenue, Microsoft Offers Buyouts to 27% of Its Staff, and Chinese Open-Weight Models May Be Done in the US
Plus Broadcom backstopping Anthropic’s chip debt, Meta’s $95B equity raise, the PHP2Shell flaws, and an IC fight over Instinct at $30B and OpenAI at $1.25T This week had one story that mattered more than everything else combined: Anthropic finally filed its S-1. Harry Stebbings, Rory O’Driscoll and I went through what’s actually in it, the…
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5 Interesting Things, Blog Posts, Scale
5 Interesting Learnings from Guidewire at $1.24 Billion in ARR: A $1.7 Billion AI Acquisition, Its Lowest Churn Ever, and 10x ARR for a 25-Year-Old System of Record
Guidewire sells core systems to property and casualty insurers: policy, billing, and claims. It was founded in 2001. Its buyers are some of the slowest-moving in B2B. In a year when the market repriced anything that looked like legacy software, it still trades at roughly 10x ARR. Fiscal 2026 closed July 31. ARR was $1,237…
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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
"SaaStr is the undisputed thought leader in how to build SaaS businesses. Jason is legendary."
Lew Cirne, CEO of NewRelic
"SaaStr has pulled the entire SaaS community together in a powerful way."
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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