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Dear SaaStr: Should We Drop Customers That Complain Too Much?
Dear SaaStr: Should We Drop Customers That Complain Too Much? Sometimes, yes. But just as often, the ones that complain are the ones that care. And oftentimes, their complaints help focus you on the gaps you really do need to fix. One thing most SaaS companies get wrong in customer success is they don’t spend…
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Jason + Lenny are Back!! “The Real Future of AI in Sales”
So in early 2024, Lenny Rachitsky invited us on to Lenny’s podcast for what became an iconic deep dive on sales and GTM. How and who to hire, the classic GTM and sales mistakes we all make, and more. It was great. It was also … an entire era ago. The end of the pre-AI…
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
We’re Literally Just Getting Started in AI + B2B. Here’s Why 2026 Is When It Gets Real.
I know, I know. You’ve been hearing about “AI transforming B2B” for two years now. Your LinkedIn feed is drowning in it. Every vendor has slapped “AI-powered” on their homepage. But here’s the thing: we’re actually just now getting to the starting line. Really. Most of this stuff didn’t even work until early 2025. 2024:…
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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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Aaron Levie, CEO and Co-Founder of Box
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