Everything’s In Play in the Age of AI: Why Only 1 of Our 16 Core AI Agents Comes From a Legacy Vendor
One of the most common questions I get from SaaS founders and operators is: “What AI agents are you actually using at SaaStr?” Everyone’s trying to figure out what actually works in this new era. So we put together a quick summary of our AI agent...
Scaling to $3B: How Clio Built a Vertical SaaS Powerhouse with AI and Innovation with CEO Jack Newton
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...
Dear SaaStr: What’s The Best Way to Fire Your Co-Founder … Who Was Once a Friend?
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...
20VC x SaaStr This Week: The Great VC Shuffle, TAM Exhaustion in AI, and Why a Billion in ARR Is “Still Early”
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...
Dear SaaStr: What are Some Early Signs a New VP isn’t Going to Be a Fit?
The top one for me is when they don’t embrace the goals given to them. I see this again and again: A VP of Sales that just sort of ignores the plan for the next quarter or two. A CMO that focuses on the types of marketing she or he likes to do, ignoring what’s...
Who Will Buy The SaaS Companies?
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...
5 Interesting Learnings From Klaviyo at $1.2 Billion in ARR
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...
Dear SaaStr: Growth Has Slowed and My VP of Sales is Pushing Me To Hire More Reps. Is That The Right Way to Go?
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...
From Zero to 20 AI Agents in 10 Months: The SaaStr Playbook for Actually Deploying AI Agents That Work
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...
From Zero to Eight Figures in 18 Months: Decagon CEO’s Playbook for AI-Native SaaS Growth. And Why They Partnered With Accel
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...
Dear SaaStr: Why Do Founders Hire So Many Terrible VPs?
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...
Why SaaStr AI London 2025 Is Where You Learn AI + GTM From The People Actually Doing It. At Scale.
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...
From Zero to Replit Fluent: How 9 Apps and 500,000 Users Taught Me to How to ‘Vibe’ Apps Into Production
After 100+ days and with 9 apps vibe coded into production with Replit used over 500,000 times we’re just getting going. And … I think key to that is that I’m now “Replit Fluent”. What does that mean? It’s a state where I know how to vibe...
Dear SaaStr: How Long Does It Take the Average SaaS Startup to “Exit”?
Dear SaaStr: How Long Does It Take the Average SaaS Startup to “Exit”? I took a look a little while back at how long it took the average SaaS company that was sold for $1B+ to get that acquisition. The answer? 11.7 years on average, with a median of 10.0...
Founder SaaStr
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