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Blog Posts, Sales
The Top 15 Questions to Ask a VP of Sales During an Interview (Updated for 2026)
One of the classic original SaaStr posts was on the Top 10+ Questions to Ask a VP of Sales Candidate. I updated it in 2025. I’m updating it again for 2026, because the world has changed even more. We’re now in a world where AI agents handle a meaningful chunk of the pipeline. Where reps…
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Blog Posts, Early, Q&A, Sales, Sales
5 Simple Tips to Quickly Improve Sales Performance
Dear SaaStr: What are the best 5 tips to improve poor sales performance? If you've never listened to your sales reps' calls, Especially the ones that are mediocre performers, You'll often be shocked what you hear. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) February 9, 2024 Here are my 5 simplest ideas to quickly improve sales performance. …
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Blog Posts, Early, Growth, Scale
Don’t Let Them (Your Best Employees) Go
When you see Founder Mode from a non-founder When you find a VP, an exec, that actually cares as much as a founder, or almost as much … Promote them fast. ASAP. Double their equity. And … never let them go. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) May 29, 2026 It seems like in the Age…
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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. We went off on...
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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