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The Top 12 Sales Lessons From SaaStr AI 2026: Anthropic, Gamma, Owner, Stripe, Salesforce, Vercel, Replit and Monaco

The sales and GTM sessions at SaaStr AI 2026 in San Mateo was all about where to take agents next.

No one was still debating whether to put agents in the revenue org. They had already done it, and they brought the war stories. What broke, and...


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Our New AI VP of Finance Closes the Deal, Sends the Invoice, and Chases the Cash. It Took 4 Deals to Train It.

Our finance team went on vacation during SaaStr AI Annual.  Our busiest time of the year.

That’s the whole origin story. Collections started slipping, sponsors and vendors weren’t getting billed, and the work that has to happen after a deal closes stopped happening, at the time of the year when time matters most.

It’s was time to bring in an agent ;). Our f...


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Build on the Stack You Have: How Anthropic’s Head of Industries, Atlassian’s Head of AI, and Scale’s Rory O’Driscoll...

Three of the strongest sessions at SaaStr AI 2026 came from three very different seats. Sharif Mansour runs AI and the product management craft across Atlassian’s 20+ apps and 450 product managers. Eleanor Dorfman leads the commercial and industries sales team at Anthropic. ...


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Dear SaaStr: When Should We Start Pushing For Multi-Year Contracts?
Dear SaaStr: When Should We Start Pushing For Multi-Year Contracts? For most of us: stop pushing for them in the Age of AI. The market has shifted, and fighting it costs you more than it gains.

Here’s the reality: shorter contracts are now the norm across B2B + AI, and it’s rational buyer behavior, not a negotiating tactic.

A...


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We Peaked at 30 AI Agents. Now We’re Coming Back Down to 20. Here’s What Consolidation Actually Looks Like. The Agen...

We run SaaStr with 3 humans and 21+ AI agents. This is a real eight-figure B2B business with real customers, real invoices, and a real collections problem, and the agents run it.

About a month ago we hit a wall. Amelia and I realized we could not manage one more agent.

Some precision on what that means. Agents managing invisible sub-agents, fine, there can be a ...


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