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A Quiet Salute to the CEOs Still Rebuilding for the Age of AI. Most Are Maybe 40% Of The Way There.
The CEOs I have the most respect for today? The ones truly rebuilding their companies for the Age of AI. Not just sort of, kind of, doing so. Not the ones who shipped AI features and put them on the pricing page. I mean the ones tearing up how the product works, how it’s priced,…
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5 Interesting Things, Blog Posts, Scale
5 Interesting Learnings from Box at $1.29 Billion in Revenue: 17% Billings Growth, 106% NRR, and 20 Basis Points of AI Margin Cost
Box reported Q2 FY27 and saw real if modest acceleration: Revenue of $321.1 million, up 9% and up 11% in constant currency. Non-GAAP operating margin of 29.4%. Non-GAAP EPS of $0.40 against a $0.39 guide. Free cash flow of $59.7 million, up 67%. Box is one of the cleanest live tests in public B2B of…
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Blog Posts, Exit, Exit Strategy, Leadership, Q&A
Dear SaaStr: Why Do Many Startup CEOs Quit After Their Companies Are Acquired?
Dear SaaStr: Why Do Many Startup CEOs Quit After Their Companies Are Acquired? Five reasons: First, it’s very difficult for most founder-CEOs to work for someone else. They generally don’t mind working with others. They don’t even need to be “the boss”. But being told what to do, especially when it’s not clearly “right”? Tough….
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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
"SaaStr is the undisputed thought leader in how to build SaaS businesses. Jason is legendary."
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
"SaaStr is definitely the largest collection of people who like enterprise software — on the planet."
Aaron Levie, CEO and Co-Founder of Box
"SaaStr’s all about helping the younger founders be successful."
Phil Fernandez, CEO & Co-Founder of Marketo
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Dharmesh Shah, CTO of Hubspot
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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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