Where does your CMO sit in the org chart? It’s a question that reveals more about your company’s growth stage and strategic priorities than you might think. New data from Pave reveals the latest patterns in how marketing leaders report across company...
Two of the most misunderstood concepts in AI for B2B and SaaS aren’t technical—they’re human. “Human-in-the-loop” and “AI orchestration” have been watered down into feel-good phrases that make AI adoption sound effortless. The...
It's not a flag when a founder picks new VCs for the next one Many reasons for this It's a pretty big flag when none of a founder's last VCs want to invest in the next one Are exceptions, but usually a sign — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin...
“This is the most stressed I’ve ever been. And that’s actually a good sign.” — Aaron Levie, CEO Box “Right now we’re in an environment where nobody can take any of their position for granted,” Levie shared during our...
Dear SaaStr: How Do I Know If My New VP of Marketing Is Working Out? It’s tough. Way too many senior marketers today just want to be strategists. Or just manage a few agencies and work on brand. That’s not what you need. You’ll know if your VP of...
5 Things Vanta Got Right and 5 They Got Wrong getting to the first $10m ARR When Christina Cacioppo co-founded Vanta in 2017, security compliance was an afterthought for most startups. Fast forward to 2025, and Vanta is valued at $2.45 billion with over 8,000...
When Anthropic hit a reported $4 billion in annual revenue at the end of 1H’25, it marked more than just another AI milestone. It validated a completely new category of B2B growth that’s operating by fundamentally different rules than anything we’ve seen...
I spent the other deep in vibe coding on Replit for the first time — and I built a prototype in just a few hours that was pretty, pretty cool. Getting into commercial-grade, enterprise-grade shape is different, though. But to start it’s amazing: You can build an “app”...
Dear SaaStr: My Customer Hasn’t Paid. When is it Worth it to Hire a Collections Agency to Get The Money? Never. I know it’s frustrating, but if you’ve turned off the app and they still won’t pay, it’s just time to move on. It’s almost...
Anthropic is ~40% as big as OpenAI by ARR, despite its consumer app Claude being just 5% the size of ChatGPT. The AI race isn’t just about who has the most users—it’s about who can monetize their technology most effectively. While OpenAI dominates...
