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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai

SaaS Isn’t Dead. But the Way You Used to Win in B2B? That’s Gone.

There’s been a massive SaaS sell-off since mid-2025. Multiples compressed. Growth stocks punished. The “SaaS is dead” takes are everywhere again. B2B isn’t dead. Software is still eating the world. Businesses still need tools. Enterprise software spend is accelerating in 2026 at the highest rate in years, and the highest absolute rate ever. But what…
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai

SaaStr AI 2026 is Running 132% of Last Year. But It’s Not Remotely That Simple. It Could Have Been -46%

SaaStr AI 2026 is running 132% of where we were at this point last year. Tickets are up. Sponsors are up. See everyone in San Francisco, May 12-14. We’ve got the best of the best coming — Databricks, Replit, Agentforce, Lovable, Google Cloud, and so much more. It should be a moment to just celebrate,…
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Blog Posts, Q&A

Dear SaaStr: When Is It Worth Enforcing an Autorenewal Clause if the Customer Doesn’t Want to Pay?

Dear SaaStr: When Is It Worth Enforcing an Autorenewal Clause if the Customer Doesn’t Want to Pay? Dear SaaStr: When Is It Worth Enforcing an Auto-Renewal Clause if the Customer Doesn’t Want to Pay? Never. Just turn it off. Auto-renewal clauses are absolutely worth having in your contracts. You really don’t want to chase customers…
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Blog Posts

20VC x SaaStr: Anthropic Raises $30B, The B2B Software Gravity Well, and Why Corporate America Is Willing AI Into Existence

With Harry Stebbings, Jason Lemkin, and Rory O’Driscoll Anthropic raises $30 billion at a $380 billion post-money. Thrive closes a $10 billion fund the same week. OpenClaw’s creator joins OpenAI. Workday’s founder comes back. And public B2B software keeps getting dragged into a gravity well it can’t escape. This week’s episode was dense. Here’s what…
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Blog Posts

Debt Isn’t Free: What Every B2B Founder Needs to Learn from Divvy Homes’ $1 Billion Exit Where Founders and Most VCs Got $0

Divvy Homes just sold to Brookfield Properties for $1 billion. The founders got $0. The employees got $0. Even most of the venture investors got $0. A billion-dollar exit. Zero for the people who built it. A company that once had a $2.3 billion valuation, that raised from a16z and Tiger Global, that helped 2,000…
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Blog Posts

When The #1 Sales Rep Stumbles

So several times now I’ve seen the #1 sales rep that was just crushing it for quarter after quarter … then a few years down the road … later become one of the lowest performers. From #1 to the bottom of the leaderboard. And the fall often happens pretty quickly, even if at the time,…
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