Being a “System of Record” Won’t Save You. It’ll Just Make Your Decline More Comfortable.
I’ve been talking to a lot of B2B and AI leaders lately, and there’s a narrative I keep hearing from incumbents that’s starting to worry me: “We’re the system of record. We’re safe.” They’re not wrong per se. Not...
If Your AI Feature Didn’t Materially Boost Revenue, It Doesn’t Count. Try Again.
Congratulations! You shipped a big AI feature. You hired a “Head of AI.” You built a copilot. Your deck has a whole slide on your AI strategy with a nice gradient and some neural network imagery. None of that matters. Here’s what matters: Did it move...
The 4 Levels of Prompt Portability: Why Some AI Agents Will Hold Retention and Most Won’t
We published a piece the other day — “The Wave of AI Agent Churn To Come: Prompts Are Portable” — and the responses were sharp and fierce. Especially: “OK, I get it. But is MY AI category actually at risk?” Every AI agent founder...
The Rise of the “N=1” App: When Building It Yourself Really Beats Buying It.
So we built 2 more vibe coded app for SaaStr. Even though we didn’t want to. We’re already managing 20+ AI agents and 10+ vibe coded apps and are strapped for time. But it was worth it. Because the ROI was high, the need was acute, and we just couldn’t get the...
Dear SaaStr: Should I Run 20+ AI Agents the Way SaaStr Does?
Dear SaaStr: Should I Run 20+ AI Agents the Way SaaStr Does? The honest answer: probably not entirely like us. But you should start now — because the gap between teams who have been running agents for 12 months and those who haven’t is compounding every week....
The Honest Reason AI Will Beat Many Sales Reps: They Don’t Really Do A Lot Of The Work. But Agents Do and Will.
Here’s something I’ve been thinking about a lot lately. Everyone’s worried AI is coming for sales jobs. And yes, it is. But maybe not for the reasons you think. The uncomfortable truth? AI isn’t going to replace great sales reps. It’s...
The Cowan Paradox: Why AI Agents Won’t Let You Do Less Work. They’ll Make You Do More.
AI agents don’t free us from work. They make us do even more work to keep up with competition and customer expectations. Quarterly releases? Gone. Sales reps getting back to you in a few days? Over. The customer being responsible for their own deployment? A...
“Digital Jason” Hit 2.7 Million Conversations in 12 Months (!). Here’s What I Learned Cloning Myself.
So about a year ago, we built “Digital Jason” — our first AI Agent. It was all we had until June/July 2025 — and we learned so, so much from it. Digital Jason is an AI version of me, trained on: 13 years and 4,600+ posts of SaaStr content thousands...
If You’re Behind on AI, Put Your 10-20 Best Engineers in a Different Building. Today.
Not every B2B company needs to panic right now. Some of you shipped AI agents early. Some of you have been rebuilding your product around AI for 18+ months. Some of you already have agents in production, doing real work for real customers. This post isn’t for...
How Big of a Sales Team Do You Really Need at a Hot AI B2B Startup? The Two Playbooks.
One of the most common questions many of us are wrestling with now: just how many reps do I actually need now? And there are two very different playbooks being run right now across the fastest-growing AI companies. Both work. Both have real trade-offs. And the one you...
We Have 30 AI Agents in Production. Here Are the Top 5 Issues No One Talks About
We’ve been running AI agents in production at SaaStr for about 10 months now. What started as a couple of experiments has turned into almost 30 agents and vibe-coded apps running across our GTM stack — from outbound sales to inbound qualification to internal...
We’re Still Early to AI — And Your Team Needs More Help Than You Think
I had a moment last week that reminded me just how much work we still have to do in getting our teams up to speed on AI. I sat down with a VP Finance I’ve worked with for years. Smart guy. Strong background, knows the classic tools cold. Been in B2B for a...
10 Months Ago, We Were Barely Using Salesforce. Now It’s Our AI Agent Hub.
Here’s what no one tells you about deploying 20 AI agents across your business: they all need somewhere to live. Ten months ago—Salesforce had almost become shelfware for us. Even though I’ve been a customer for 20 (!) years. Why? Our sales team had...
Claude is the Fastest Growing Enterprise Product Ever — And It Makes It Simple to Cancel. Why Do You Make It So Hard?
I pay $100/month for Claude Max. It’s the single most important tool I use every day. I’ve built 10+ production apps on it. I run my entire business through it. I’d pay double. And yet — right there in my billing settings — there’s a simple...
Founder SaaStr
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