by Jason Lemkin | Oct 24, 2025 | Blog Posts
The 17-Year Journey: From Cloud Pioneer to AI-Powered Platform When Jack Newton and his elementary school best friend Ryan Wong founded Clio in 2008, they were building the very first cloud-based practice management system for lawyers. It was a radically different...
by Jason Lemkin | Oct 24, 2025 | Blog Posts, Q&A |
Dear SaaStr: What’s The Best Way to Fire Your Co-Founder Who Was Once a Friend? It’s pretty common that a co-founder doesn’t work out, unfortunately. I’ve been a part of all versions of this: I’ve had a great co-founder that went the...
by Jason Lemkin | Oct 23, 2025 | Blog Posts
We’re back!! Jason Lemkin, Harry Stebbings, and Rory O’Driscoll diving into the startup and venture capital conversations that actually matter—from Benchmark’s masterclass in talent acquisition to why billion-dollar ARR companies are “still...
by Jason Lemkin | Oct 22, 2025 | Blog Posts, Exit
We’re sitting on a really big problem in SaaS nobody wants to talk about much. The exits … are no more. For years, we had a predictable exit playbook: Build a solid SaaS company to $20M-$50M in ARR Maintain decent growth, and … The buyers would come. Private...
by Jason Lemkin | Oct 22, 2025 | 5 Interesting Things, Blog Posts, Scale
5 Interesting Learnings From Klaviyo at $1.2 Billion in ARR Perhaps the most undervalued public B2B / SaaS leader today. At just 6.1x ARR multiples with 32% YoY growth, Klaviyo is trading at a significant discount to peers with similar growth profiles. The company is...
by Jason Lemkin | Oct 22, 2025 | Blog Posts, Q&A |
Dear SaaStr: Growth Has Slowed and My VP of Sales is Pushing Me To Hire More Reps. Is That The Right Way to Go? No. Not 9+ times out of 10. In fact, the #1 sign your VP of Sales is really struggling is when their best answer to slowing sales is to hire even more...
by Jason Lemkin | Oct 21, 2025 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
A deep dive into the playbook, lessons learned, and brutal truths about deploying 20+ AI agents into production — that actually work. During Dreamforce Jason (CEO) and Amelia (Chief AI Officer) at SaaStr dropped by Qualified’s office for a deep dive on its AI Agents...
by Jason Lemkin | Oct 21, 2025 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
A SaaStr Annual + AI Summit conversation with Jesse Zhang, CEO of Decagon, and Sarah Ittelson, Partner at Accel Decagon Today: The Numbers Behind the Hype Founded in late 2023—just months after GPT-4’s release—Decagon has become one of the fastest-growing AI...
by Jason Lemkin | Oct 21, 2025 | Blog Posts |
Dear SaaStr: Why Do Founders Hire So Many Terrible VPs that Mislead Them? I think it’s a combination of three factors: Trusting your team. It’s hard to scale if you don’t. Needing a team. You can’t do it all yourself. And Hiring folks to do something you don’t know...
by Jason Lemkin | Oct 20, 2025 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
It’s time. It’s time to get ahead of the pack in AI + B2B. Not next quarter. Not next year. Right now. Because the companies that figured out AI in GTM over the past 12 months are now scaling those playbooks aggressively. They’re closing bigger...
