That First Magical Sales Rep. The AI Era Edition.
A while back on LinkedIn and Twitter we had over 200,000 views and engagements on a quick post on “The Magical Sales Rep”, and another 500+ likes on a follow-up. It’s worth a deeper dive. Especially now in 2026, where the role of that first rep has...
How Owner.com’s CRO Is Closing $2M+ in ARR Per Rep With AI: 5 Things You Can Steal
At SaaStr AI 2026, Kyle Norton, CRO of vertical AI leader for restaurants Owner.com, walked through how his team is generating outcomes that look almost impossible on paper for traditional B2B. Owner sells vertical AI to independent mom-and-pop restaurants (think...
For Frack’s Sake, It’s Not Too Late to Ship an Epic AI Agent. And Get Back to Real Growth.
So I spent the other day writing a fairly dark post about how most traditional B2B leaders will slowly atrophy to nothingness. Maybe seven survivors, everyone else decays, Medallia as the cautionary tale, but just one of many: Medallia Is Just the Opening Act: 12+ PE...
Top 10 Learnings From Building Our Own AI VP of Customer Success “Qbee”
We’ve now rolled out 21+ AI agents and 12+ vibe coded apps at SaaStr AI, used 1,100,000+ times. AI SDRs. An AI VP of Marketing (10K) that in many ways now manages us, not the other way around. AI-powered VC tools that have run over a million startup valuations....
Don’t Lose a Great CoFounder, Whatever It Takes
So when I look back on my many failings as an entrepreneur, in the end, it’s all about the team.  Almost all my failings as a CEO and founder came from failing to get that one extra great VP hired, that one critical hire. And cofounder is the most complicated of all....
Why 95% of Customer Success Managers Can’t Be Turned into Forward Deployed Engineers. And What That Means.
Every B2B company right now is staring at the same problem: they need more Forward Deployed Engineers, they don’t have enough of them, and they’re looking at their CS team wondering if they can bridge the gap. Usually, they can’t. Here’s why —...
The Agents Episode #005 is Out! Our 2 AI VPs Cost $257/Month, a Website Willed Itself Into Becoming an Agent, and QB Sent 83 Personalized Emails at 12:20am
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....
Even a Mediocre Prompt Can Build Pretty Good Software Today
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...
SaaStr AI App of the Week: Helply. The Bootstrapped B2B Support Platform That’s Free Forever, Charges Only When AI Actually Resolves a Ticket, and Showed Up to SaaStr AI 2026 With Giant Pandas
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...
Forget “Would You Hire Them Again.” The Real Test Now Is Whether You’d Replace Them With an Agent.
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...
20VC x SaaStr: Anthropic at $900B+, Salesforce Spends $300M on Tokens, SpaceX Files for the Biggest IPO in History, and Why the Tech Lash Is Just Beginning
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,...
How Anthropic Rebuilt Its Sales Org From Scratch When Demand Went Vertical: 54% of New Enterprise Logos Now Come Self-Serve
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...
The Modern GTM Org in 2026: 20-30% Leaner, 9x Flatter, ~2x More Net New Revenue Per Rep. The Latest from ICONIQ Growth.
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....
High NRR is Magic. It Can Also Hide a Lot of Problems.
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...
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