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20VC x SaaStr This Week: Anthropic Is Eating OpenAI’s Enterprise Lunch, Figma’s Real Problem Isn’t Stitch, and the Unicorn Math Nobody Wants to Talk About
With Harry Stebbings, Jason Lemkin, and Rory O’Driscoll We’re back! Ramp data put a number on what OpenAI has been avoiding: 73% of new enterprise AI spending is going to Anthropic. Ten weeks ago it was 50-50. That shift — plus a Figma stock rout, a $100B Bezos bet on AI-transformed manufacturing, a $20B Grok…
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Artificial Intelligence (AI), Blog Posts, Customer Success, SaaStr.Ai
Our AI Customer Success Agent Is Working Harder Than 95% of Human CSMs I’ve Worked With. Maybe More Than 95%.
Here’s what happened yesterday. At 8:37am, our AI Customer Success “QBee” agent sent out 150+ personalized sponsor update emails for SaaStr AI Annual 2026. Not a batch blast. Not a mail merge with a first-name token. Every single email was genuinely customized to what exactly we needed from them to … succeed for them: unique…
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Blog Posts, Sales
Faster Closes. Shorter Contracts. Leaner Teams. The Top 10 Learnings From the Latest ICONIQ GTM Report.
ICONIQ just published their State of Go-to-Market in 2026, based on a January 2026 survey of GTM executives at 150+ B2B + AI software companies. The data is always good, Iconiq invests at the growth state in a large cross section of the best in B2B + AI. Here are the 10 findings that matter…
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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
"SaaStr is definitely the largest collection of people who like enterprise software — on the planet."
Aaron Levie, CEO and Co-Founder of Box
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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...
How To Reverse-Engineer a $100M Exit: SaaStr on My First Million Pod
How do you reverse-engineer your first million as a SaaS startup founder? SaaStr founder and CEO Jason Lemkin chats with Sam Parr on the popular YouTube channel and podcast My First Million about what’s required to make it on the map for a $100M exit and then reverse engineers the steps to get there.
Rule 1: New minimum is $400K per employee
Rule 2: Go multi-product
Rule 3: Your second product must be bigger than your first product
Cheat code: Double your prices
Rule 4: 30% of your revenue is international
Rule 5: Localize your product
Cheat code: Remove friction
Rule 6: 100% net revenue retention
Rule 7: Don’t raise double digit millions
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