Amelia and I just recorded Episode 005 of The Agents right before 2026 SaaStr AI Annual. You may have missed it in all the fun of the big event, here’s your chance to catch up! Most importantly: we both got the cost number completely wrong for our AI Agents. Our AI VP of Marketing (10K)…
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Dear SaaStr: As a Startup, What Are Some Effective Ways For an Underdog to Take Down Their Competition? It depends on the gap. In B2B historically, I’d argue if your competitor is larger than you, at $8M-$10M+ in ARR and growing quickly, with even reasonably happy customers, then it’s too late. Too late to “take…
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Here’s the exact prompt I typed into Replit the other day “ok i have an idea where we built a new speaker card page, where if you upload a headshot, we build you a 1080×1080 card on a background you pick from (one is attached) and show your headshot and ‘I’ll Be at SaaStr AI…
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The Bottom Line: Alex Turnbull bootstrapped Groove from $0 to $5M ARR as a solo founder over a decade. Then he bet against his own playbook. Helply is the AI-native B2B support platform he’s building in public. The support platform itself is free forever. No seats, no caps. You only pay when AI delivers a…
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Dear SaaStr: A Big Tech Co Launched a Competitive Product. How Can I Tell How Serious They Are About It? In B2B at least, I’ll give you a few metrics that are fairly reliable. The classic one still works, but in 2026 you need to layer in some new signals too. The classic test: How…
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For our entire careers in tech, the standard management test has been: “Given what you know now, would you hire this person again?” It’s a decent HR framework. It forces honesty. If the answer is no, you have your decision. But in 2026, the question is incomplete. The real test now is: “Would you replace…
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With Harry Stebbings, Jason Lemkin, and Rory O’Driscoll Anthropic is closing $30 billion at a $900 billion valuation. That’s nearly triple the $380 billion price from February. Andre Karpathy joined Anthropic the same week. Cerebras priced its IPO at $185, popped 68% on day one, and broke $300. SpaceX set June 12th as the date…
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Dear SaaStr: Should Your Ask a Prospect What Competitors They Are Looking At? Yes. And in 2026, more than ever. You’ll find 90% of the time you’ll want to not just tell a prospect who you are competing with, but do so aggressively. And box the competition out at the start. “Great to learn about…
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When Claude Opus 4.6 shipped in December 2025, Anthropic’s commercial team came back from winter break to find demand had gone vertical. They hadn’t hired for it. They hadn’t planned for it. As Eleanor Dorfman, Anthropic’s Head of Industries who runs the commercial and industries sales team, put it on the SaaStr AI Annual 2026…
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ICONIQ just released their latest 2026 GTM benchmark report, surveying 150+ B2B software companies in January. The findings line up with what we’re seeing in our portfolio, what we saw at SaaStr AI Annual 2026, and what we’re doing inside SaaStr itself. Our top 9 take-ways: 1. The AI productivity gap is now $270K per…
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Having high net revenue / dollar retention is the magic of B2B. If you have 120% NRR, you double in less than 5 years, even with no new customers. Above that, you really get into magical compounding growth. But here’s the 2026 reality check: high NRR has gotten rarer than it used to be. Median…
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Most of the discussion about AI agents in B2B right now treats the agent as a feature you ship: a chat box, a copilot, a magical button inside your product. That framing has been throwing people off, including me, for the past year. What’s actually working at SaaStr AI, and the reason 10K and QBee…
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On paper, this was a strong quarter for HubSpot. Maybe not epic, but strong. HubSpot reported Q1 ’26 with revenue of $881M, up 23% … as reported. Subscription revenue alone hit $862.3M, putting ARR run-rate around $3.45B. They beat consensus by $18M. Customer count crossed 299,458, up 16% YoY. Non-GAAP operating margin expanded 380 bps…
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Recently I was catching up with a good friend who used to be CEO of an enterprise-y B2B social networking company. The usage and engagement numbers of his business were just awful. Customers bought because they thought their organizations needed this functionality, and so they wrote the checks for Year 1, and even Year 2….
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Live now: saastr.ai/api-report-card When we shipped the AI Agent API Report Card a few weeks ago, we had 75 B2B APIs graded and a hunch this was a tool builders had been quietly waiting for.   A few weeks in, the numbers tell the story: 144 APIs graded. 4,521 analyses run. 45 A grades. 87…
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