If You Are at Scale, You Now Have 2 Full-Time Jobs: Keep Your Installed Base Happy. And Winning the AI Agent War in Your Space.
Here’s what I see at almost every B2B company that has crossed $50M ARR right now: The CEO is running two completely different, completely demanding businesses at the same time. And most of them are only really showing up for one. The first job is the one they...
Top 10 Learnings from Sapphire Ventures’ 2026 Software x AI Report: 80+ $100m ARR AI Startups, The Ultra Round is The New Normal, and Enterprise is 50%+ of VC Now
Sapphire Ventures just released their 2026 Software x AI Report and while we’ve seen some of its data we’ve seen before, it’s useful to see it as Sapphire is 100% focused on enterprise. Here are 10 interesting learnings from the report that every...
Who Gets an FDE, and Who Doesn’t: The Great B2B + AI Debate Right Now
I was catching up with one of our favorite AI agent vendors the other day. Strong product. Strong traction. One of the ones we recommend. And they told me: going forward, only customers with 5,000 or more employees get a dedicated Forward Deployed Engineer. Everyone...
Our Own Agent Deleted Amelia, HubSpot Gave Us a Zero, and 100 Days Since I Opened Canva: The Latest In The Agents #002
Amelia and I just released Episode #002 of The Agents. Three humans, 20+ agents, revenue went from -19% to +47% YoY, and every week we talk about what’s actually working, what’s breaking, and what you should do about it if you’re deploying agents at...
The Real Reason B2B Stocks Are Crashing in 2026: The Software Just Isn’t Good Enough for the AI Age. Not Anymore. The Latest Case Study Here.
This week’s case study: Marketo. Why have public SaaS stocks crashed? Why are pre-AI unicorns seeing their growth stall out, in many but not all cases? The answer isn’t actually that complicated. They just aren’t very good software anymore. Not in...
The Top 10 Private AI Companies Are Now Worth More Than Every Public SaaS Company Combined
This is one of those charts that makes you stop and stare for a minute. The Top 10 private enterprise software companies: $1.93 trillion in aggregate value. The entire Sapphire Pure SaaS Index of 115 public companies: $1.88 trillion. Same total value. Ten companies on...
No Lead Left Behind: The Simplest and Most Important Reason AI Agents Actually Work in GTM
I’m sometimes slow to see the obvious. We’ve been running AI agents in production at SaaStr AI for about 10 months now. 20+ agents across Artisan, Qualified, AgentForce, Monaco, Momentum, custom Replit builds, Slackbots, and more. We went from 20+...
It’s Not Just You. Customers Are Asking for Shorter and Shorter Contracts in the Age of AI
I was at a board meeting for a fast-growing AI + B2B startup that just crossed $100m+ ARR and brought on a VP of Sales. He was exasperated. “The good news? Everyone wants to buy. The bad news? They aren’t sure what they want in AI next year. So no one...
What Moat? 18-Month Headstarts Are Now Compressed Into Being a Weekend Ahead of Your Competitor. Here’s Our Latest Real World Example.
Big features like Localization used to give you a 12-18 month moat. And we just did it in a Waymo ride. Back in the day, pre-AI, we used to beat DocuSign head-to-head. At Facebook. At Google. At Yelp. At Twitter. At a lot of the biggest tech companies of the era....
Our AI VP of Marketing Shipped 3 New Campaigns on Saturday. Come Build Yours May 12.
At 12:41pm yesterday, my inbox pinged. Not from a human. From 10K, our AI VP of Marketing. Subject line: Marketing Plan v2 — 24 days to SaaStr Annual 2026. Body: Three campaigns, sized, drafted, and ready to ship. Replaces yesterday’s plan with one new campaign...
Salesforce Just Launched Headless for AI Agents. We’ve Already Been Living It for 6 Months.
Marc Benioff announced Salesforce Headless 360 this week: “No browser required. Our API is the UI.” For anyone running real AI agents in production, this isn’t a product announcement. It’s a description of what’s already happening. Marc...
10+ Live Vibe Coding Classes at SaaStr AI Annual 2026. Taught by Replit + Team SaaStr. Because Waiting on Engineering Is Over.
At Team SaaStr we’ve personally shipped 12+ production apps on Replit in the past year. Our AI VP of Customer Success (QBee) runs on Replit. Our AI VP of Marketing (10K) runs on Replit. Together they’ve saved us roughly 70% of the human hours we used to...
Why So Many Are Struggling in the AI Era: They Are Shipping 60% Solutions
HubSpot is one of the greatest classic SaaS and B2B companies of all time. The majority of the SaaStr AI community runs on HubSpot. We are big fans. But … I just tried HubSpot’s new AEO (AI Engine Optimization) tool announced as part of its big new AI...
Introducing “The Agents”: A New Weekly Show Where We Share Everything Happening With Our 20+ AI Agents in Production. The Good, The Bad, and The Broken.
We get asked about our agents probably 50 times a week. CEOs of public companies. Founders just deploying their first AI SDR. RevOps leaders trying to figure out if they should build or buy. Everyone wants to know what’s actually happening behind the scenes when...
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