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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
We Vibe Coded Our AI VP of Marketing. Here’s What It Actually Does.
We didn’t want to build it. We run 20+ AI agents at SaaStr. We’ve invested over $500K in AI infrastructure. We follow one rule religiously: buy 90% of what you need, only build the 10% where no solution exists. We call it the 90/10 rule, and it’s saved us from a lot of wasted time….
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
It Took Apple 42 Years to Reach $1 Trillion. Anthropic Will Do It in 5.
AI has reset everything we knew about the pace, size and scale of company building. At least for the true outliers. The first: Anthropic raised $65 billion at a $965 billion valuation and filed confidentially for an IPO. Founded in 2021. That puts it on track to cross $1 trillion in roughly five years from…
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Blog Posts, Growth, Marketing
Your VP Sales Has a Sales Quota. Your VP Marketing Has To Have a Quota, Too.
One of the first iconic SaaStr posts was Hire the Right Type of VP Marketing or You’ll Just End Up With a Bunch of Blue Pens with Your Logo On Them. The basic idea was to help folks who haven’t hired a VP or Director of Marketing hire the right one for a pre-Scale sales-driven…
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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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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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