The Navan IPO Reminds Us: AI is On Fire. Everything Else in B2B? Still Really, Really Hard.
So Navan finally went public in Q4’25. After years of confidential filings, pushed timelines, and a rebrand from TripActions, they rang the bell on October 30th, 2025. And then the stock dropped 20% on Day One. Today? It’s trading around $17. That’s 32%...
A Big Year for SaaStr AI: What We Got Done in 2025
2025 was our biggest year of transformation since launching in 2012. We went all-in on AI. Not just talking about it—actually deploying it across our entire business. Here’s what we shipped: 🤖 From Zero to 20+ AI Agents We started 2025 AI-lean. By mid-year, we...
The 10 Rules For Hiring a VP of Sales in the Age of AI
The plays are the same — but the rules have changed. Here’s what actually matters now. We’ve been writing about hiring VPs of Sales / CROs for 12+ years (!) at SaaStr. We’ve said — and it’s still true — that about 70% of first VP Sales hires...
The Quirky Math Behind M&A Pricing in Tech: Why $125M ARR Can Be Worth $2B+… And Then Disappear
M&A pricing can be a weird thing Meta buys Manus for $2B+ at $125m ARR Then likely … abandons all that revenue. It is a distraction, and in the end, immaterial to Meta’s revenues. Whatever Meta does with it, it likely won’t be investing more in the current product...
Dear SaaStr: How Does a B2B Startup Break Out in a Crowded Market?
Dear SaaStr: How Does a B2B Startup Break Out in a Crowded Market? Find one segment of the market to win in. Where you can build a 10x feature, and then a 10x solution, that solves a niche problem that customers will pay for. Most B2B markets are crowded today. In...
My Top 10 Learnings from 37 Podcasts with Harry Stebbings and Rory O’Driscoll This Year
Harry Stebbings. Rory ODriscoll and I have done 37 podcasts together this year (!). We didn’t miss a week. But man, the world changed in those 37 weeks. My top learnings… and what’s changed: #1. I Won’t Do a T3D2 Investment Again I know this...
OpenAI’s GTM Lead Maggie Hott: No Commissions, 100% Pilot Win Rates, and the Race Against Incumbents
Most of what you hear about sales hiring is recycled advice: look for humility, avoid blamers, hire for grit. Fine. True. Not interesting. But buried in a recent conversation with Harry Stebbings and Maggie Hott — OpenAI’s GTM leader who built ChatGPT Enterprise...
Dear SaaStr: We’re Running Out of Money and Can’t Raise. When Do You Call It a Day?
Dear SaaStr: I am running out of runway and in our fundraise we so far have had no luck with termsheets. when is the right time to call it a day? It’s tough, but here’s the reality: you call it a day when you’ve exhausted every reasonable path to survival and growth,...
Can You Really Grow in 2026 if You Aren’t Tapping into AI Budget?
Can you really grow in B2B in 2026 if you aren’t tapping into AI budget? The short answer: Probably not. Here’s the real data. It may in fact be your last, best change to tap into it. Something fundamentally different happened in 2025. AI budgets stopped being...
How We Turned Around SaaStr’s Traffic in 12 Months by Going All-In on AI. From a -19% Decline to a +47% Growth.
From -19% Decline (1st half year) to +47% Growth (2nd half year): What Actually Happened That’s a 66% swing in growth in SaaStr readers over the course of 2025. Over less than 12 months. At the start of the year, SaaStr website traffic while still substantial...
Dear SaaStr: What Was the Moment You Knew You Had to Break Up With Your Co-founder?
Dear SaaStr: What Was the Moment You Knew You Had to Break Up With Your Co-founder? It’s happened to me twice, that “moment”. It was the same thing both times: When they just didn’t show up to a critical meeting. Founder conflict is unfortunately pretty common. I was...
One Reason The Best AI B2B Startups Are Growing So Quickly: Truly Insane Value
We talk a lot about what’s driving the fastest-growing AI startups. Is it the technology? The timing? The TAM expansion? All of that matters. But it’s also something that’s easy to overlook because it’s almost too obvious: The best AI B2B startups...
Nvidia Created 27,000 Millionaires Already. What It Teaches Us About Getting Rich. And The Power of Going Long.
There’s a lot of advice out there about how to get rich. Start a company. Invest in crypto. Build a personal brand. Have multiple revenue streams. But if you want to understand how generational wealth is actually created for tens of thousands of people at once,...
AI And The Death of The 2021 Sales Process
The classic sales plays do still work. Hard work, knowing the product cold, showing up. But the classic 2021 playbook? It’s close to dead in the Age of AI. And here’s one example of why. The other day I did something that should make every sales rep reach for the...
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