The year in review with Harry Stebbings, Jason Lemkin, and Rory O’Driscoll The year that changed everything is almost over. In this special year-end episode, Harry Stebbings, Jason Lemkin, and Rory O’Driscoll break down the founders, funds, and companies...
Jason’s Full AMA from SaaStr AI London on What’s Really Changed in B2B Sales in the Age of AI … So Far Top 5 Takeaways The plays all still work — webinars, inbound, outbound, demos. The hottest AI companies are being run by the same B2B sales leaders...
Dear SaaStr: When Should You Sell Your Startup? Having been through the acquisition process 4x — twice as a founder, twice as a start-up exec, here’s my list of when and if to sell. Don’t take it literally. Most startups never get a single good...
We’ve now been running 20+ AI agents in production at SaaStr since May. And the transformation has been real. With just 2.5 humans + 20 AI agents, we’re now doing the same work and producing the same output as 12+ humans did before. That’s not hype —...
Dear SaaStr: How Do I Compete with a Company that has Unlimited Capital — and I Don’t? First, does your highly-funded competitor have a dominant brand yet? If not, it may not matter. There is no “winner” yet. The #1 brand trumps capital. But if they have...
One API. 300+ Models. 60+ Providers. And Why Every AI-Native Startup Needs This. We’ve featured a lot of amazing AI tools in our App of the Week series. But OpenRouter might be the most foundational one yet. Because if you’re building anything with AI —...
So it’s a bit funny, when we started SaaStr we rarely talked about the stage beyond $100m ARR. That’s what it took to go big and IPO. HubSpot, Box, Zendesk, etc. all IPO’d at around that stage. Growing very, very quickly. But around then. Helping you get to $100m...
Dear SaaStr: We’re At $3m ARR Growing 35%. What Does The Future Look Like? 1. It’s going to be a grind. At 35% growth, you’ll likely double ARR every 2-3 years. That means you could hit $6M ARR in 2 years and importantly,. $12M ARR in 4-5 years. While this isn’t...
The B2B markets bifurcated in 2025 — and the laggards all share one thing in common. 2025 has been the year of the Great B2B Bifurcation. On one side: Palantir up 142%. Cloudflare up 80%. MongoDB up 70%. Security stocks printing money. On the other side: HubSpot down...
Zendesk just announced the acquisition of Unleash, an Israeli AI-powered enterprise search startup with 70+ connectors to things like Google Drive, Confluence, and SharePoint. The pitch is “permission-based RAG” and AI agents that live inside Slack and...
