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Blog Posts, Growth
Hiring a Strong New VP? Let Them Pick Their Right Hand Person
So there’s a mistake I see a lot of founders make again and again, especially when cash is tight. In fact, these days cash is tight for most, even if you’re at $20m, $50m, $100m ARR, since everyone’s trying to get more efficient and profitable. And the mistake they make is they finally hire a…
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Blog Posts, Q&A
Dear SaaStr: Should I Visit My Customers More?
Dear SaaStr: Should I Visit My Customers More? Yes. Absolutely. Of course you should. You should visit your customers more. I can’t stress this enough—getting in front of your customers is one of the most effective things you can do to drive growth, retention, and expansion. It’s not just about building relationships, it’s about understanding…
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Blog Posts, Sponsored Posts
Rippling’s AI Bet: The Data Graph Is the Moat
Rippling’s AI Bet: The Data Graph Is the Moat Rippling’s whole AI bet comes down to one thing: a single connected database under every product it sells. Luke Prokopiak, who leads Rippling’s AI product team, spent the first two minutes of his demo on that database before he touched a model. Rippling’s employee graph is…
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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
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Scott Dorsey, CEO of ExactTarget
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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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