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5 Interesting Things, Blog Posts, Scale
5 Interesting Learnings from Shopify at $14B in Revenue: 34% Growth, 18% Free Cash Flow Margins, and AI Orders Up 3x
Shopify reported Q2 2026 this week and the stock jumped roughly 18% on the news, erasing most of a 25% year-to-date decline in a single session. The headline numbers: $3.58 billion in quarterly revenue, up 34% year-over-year $115.6 billion in GMV, up 32%, the fifth straight quarter of 30%+ GMV growth $1.71 billion in gross…
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Blog Posts, Hiring, Human Resources
If You Don’t Think You Need a VP of Product, VP of Marketing, Etc. — Then You Haven’t Worked With a Great One
If you are between $1m and $20m ARR, and maybe even a bit later, this might be the #1 most important post and piece of advice I can give you: That yes, a truly great VP for any role will move the needle. A truly great one. And if you don’t think so —…
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
I Bought 30+ APIs This Year. Only Exa Asked How It Went. Copy Them.
Four sentences, from a real PM, timed off actual usage. It got a 400-word product spec back. We run 21+ AI agents in production at SaaStr, and we’re building SaaStr AI Connect on top of them. That means a lot of API signups: search, enrichment, structured data, email infrastructure, inference, storage. Somewhere north of 30…
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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
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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
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Popular Q&A
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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