20VC x SaaStr This Week: Anthropic Is Eating OpenAI’s Enterprise Lunch, Figma’s Real Problem Isn’t Stitch, and the Unicorn Math Nobody Wants to Talk About
With Harry Stebbings, Jason Lemkin, and Rory O’Driscoll We’re back! Ramp data put a number on what OpenAI has been avoiding: 73% of new enterprise AI spending is going to Anthropic. Ten weeks ago it was 50-50. That shift — plus a Figma stock rout, a $100B...
Our AI Customer Success Agent Is Working Harder Than 95% of Human CSMs I’ve Worked With. Maybe More Than 95%.
Here’s what happened yesterday. At 8:37am, our AI Customer Success “QBee” agent sent out 150+ personalized sponsor update emails for SaaStr AI Annual 2026. Not a batch blast. Not a mail merge with a first-name token. Every single email was genuinely...
Faster Closes. Shorter Contracts. Leaner Teams. The Top 10 Learnings From the Latest ICONIQ GTM Report.
ICONIQ just published their State of Go-to-Market in 2026, based on a January 2026 survey of GTM executives at 150+ B2B + AI software companies. The data is always good, Iconiq invests at the growth state in a large cross section of the best in B2B + AI. Here are the...
Dear SaaStr: Can I Convert My Customer Success Managers into Forward Deployed Engineers?
Short answer: Only in very specific cases, and it usually means you need to hire a different type of person. Most CSMs aren’t built for FDE work. That’s not a knock on them — they’re doing a completely different job. A CSM manages relationships,...
Five AI Agent Vendors Asked Us to Try Their Product This Week. Just One Got Deployed. Here’s the Difference.
This week alone, five leading AI Agent vendors reached out asking us to try their products, and another 20-30 LinkedIn’d us or emailed us hoping to get our time. From Public companies to hot startups. All of them. The problem: we already run 30+ AI Agents at...
The SaaS Rout of 2026 Is Even Worse Than You Think. For the First Time Ever, Software Now Trades at a Discount to the S&P 500.
Most of us have been doing this long enough to remember when software stocks trading at 40x forward earnings felt cheap. That era appears quite .. over. Software forward P/E multiples have now fallen below the overall S&P 500. Not at parity. Below. This has never...
Dear SaaStr: How Long Does It Take to Deploy an AI SDR?
Longer than the vendor told you. But shorter than hiring another rep. Here’s the real answer: the technology is live in days. The training that makes it actually work takes 60 days of focused effort. Most companies skip the training. That’s why most AI SDR...
You Can’t Train an AI Agent and Then Just … Go Away. We Did, It Fell Off The Rails. And We Didn’t Even Know.
We have an AI agent that we use all the time. One of our now almost 30. It’s a good one, people really like it, and importantly, it’s not directly connected to revenue. So we made a biggish mistake. We sort of ignored it once it worked and was dialed...
5 Ways to Turn Your Support Data Into a Customer Acquisition Channel with HappyFox’s Founder CEO
Shalin Jain built HappyFox to $20M+ ARR, bootstrapped, with about 100 employees. He went from 5 support reps at $1M ARR to 6 support reps at $20M ARR. Same story on sales: 6 sellers at $3M, still 6 sellers at $20M. He recently shared how his team did it by treating...
The “Buyers Won’t Trust an AI” Objection Is Already Collapsing
The most common pushback we hear when talking about AI account executives replacing human AEs goes something like this: “Buyers won’t trust an AI. They only buy from humans they trust.” I understand the intuition. In theory, it sounds reasonable. In...
Dear SaaStr: Should I Use an AI SDR Before I Have a Working Human SDR motion?
Dear SaaStr: Should I Use an AI SDR Before I Have a Working Human SDR motion? No. This is the single biggest mistake I see across all company stages, from $1M ARR startups to multi-billion-dollar public companies, and it will sink your AI SDR deployment. The Core...
You Have All the Power as a Hot AI Founder. Just Don’t Accidentally Push VCs Into “Maybe Not.”
If you’re building a hot AI startup right now, you have the leverage with VCs. Full stop. There are the best of times for you, if you have traction and a true agentic product. VCs are fighting to get into the best AI deals. Rounds are closing in days. Valuations...
Dear SaaStr: We’re At $8m ARR Growing 90% But Can’t Get a VC To Give Us a Term Sheet
Dear SaaStr: We’re at $8m ARR growing 90% but aren’t really AI Native. VCs won’t take a meeting. Is fundraising hopeless right now? Not hopeless. But brutally honest? You’re in the hardest fundraising environment we’ve ever seen, and...
We Use 1 CRM. But We Use 6+ AI Sales Agents Running 24×7. What Does That Tell Us About the Future of B2B?
Here’s something I didn’t expect when we went AI-first at SaaStr: we run one CRM. Just one. But we now run four different AI sales agents — Agentforce, Monaco, Artisan, and Qualified — all at the same time. And we might add more. This wasn’t some...
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