The latest from the 20VC x SaaStr collaboration with Harry Stebbings, Jason Lemkin, and Rory O’Driscoll Anthropic sued the federal government this week. Oracle and OpenAI scrapped plans to expand their flagship Stargate data center. Meta immediately said “we’ll take it.” CrowdStrike beat expectations and traded down anyway. And we made our public market stock…
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Dear SaaStr: What are the different strategies to retain an angry customer? Let’s start with one important learning: angry customers usually aren’t lost customers. If they’ve already decided to leave you for another vendor, they generally just go dark instead. So you still have a shot not just to save them and keep them, but…
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May 12-14. SF Bay (San Mateo County Events Center). 40 acres. 300+ sessions. 10,000+ B2B and AI leaders. SaaStr AI Annual is 60 days away, and two clocks are ticking down fast: the final speaker submission window and the final custom sponsorship deadline. Last Chance To Apply to Speak This is the last call for…
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I’ve been talking to a lot of B2B and AI leaders lately, and there’s a narrative I keep hearing from incumbents that’s starting to worry me: “We’re the system of record. We’re safe.” They’re not wrong per se. Not exactly. If you’re the system of record for HR, for finance, for CRM, for supply chain…
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Dear SaaStr: I keep hearing about “vibe coding” and founders building their own internal tools with AI. But we already pay for a bunch of B2B products. When does it make sense to vibe code something yourself vs. just buying an off-the-shelf product? Great question, and one we have strong opinions on because we’ve lived…
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Congratulations! You shipped a big AI feature. You hired a “Head of AI.” You built a copilot. Your deck has a whole slide on your AI strategy with a nice gradient and some neural network imagery. None of that matters. Here’s what matters: Did it move revenue? Did it increase ACV? Did it reduce churn?…
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Most public B2B companies right now are either decelerating or apologizing for it. Cloudflare is doing the opposite. In Q4 2025, Cloudflare reported $614.5M in revenue, up 34% year-over-year — on top of already being a $2.4B+ ARR business. That’s not a small company finding its footing. It’s accelerating its growth rate. For context, they…
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Dear SaaStr: I Want to Roll Out an AI SDR. How Do I Start? First, get clear on what you’re actually buying — and what it actually does. We’ve now been running AI SDRs at SaaStr for over a year. Multiple platforms. Real data. Real pipeline. And the honest answer is: it works. But it…
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We published a piece the other day — “The Wave of AI Agent Churn To Come: Prompts Are Portable” — and the responses were sharp and fierce. Especially: “OK, I get it. But is MY AI category actually at risk?” Every AI agent founder hopes they’re the exception. That their AI B2B product has the…
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Dear SaaStr: Do You Have to Have a Super Strong Brand Like SaaStr To Get AI SDRs to Work? Honest answer: it helps. A lot. But it’s not the thing that determines whether you succeed or fail. Let me explain what brand actually does — and doesn’t — do for AI SDR performance, because I…
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The Rise of the “N=1” App: When Building It Yourself Really Beats Buying It So we built 2 more vibe coded app for SaaStr. Even though we didn’t want to. We’re already managing 20+ AI agents and 10+ vibe coded apps and are strapped for time. But it was worth it. Because the ROI was…
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Dear SaaStr: Should I Run 20+ AI Agents the Way SaaStr Does? The honest answer: probably not entirely like us. But you should start now — because the gap between teams who have been running agents for 12 months and those who haven’t is compounding every week. Let us give you the real picture. What…
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Here’s something I’ve been thinking about a lot lately. Everyone’s worried AI is coming for sales jobs. And yes, it is. But maybe not for the reasons you think. The uncomfortable truth? AI isn’t going to replace great sales reps. It’s going to replace the ones who were never really doing the job in the…
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AI agents don’t free us from work. They make us do even more work to keep up with competition and customer expectations. Quarterly releases? Gone. Sales reps getting back to you in a few days? Over. The customer being responsible for their own deployment? A relic. Every AI vendor is selling you the same dream:…
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The RevenueCat State of Subscription Apps (SOSA) 2026 was released recently, and it’s the most data-rich benchmark report on subscription app performance available anywhere. Built from 115,000 apps, $16 billion in revenue, and over a billion transactions, and the real data from 50%+ of mobile subscription apps. (As a side note, proud that SaaStr Fund…
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