“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...
The Boomerang Founders: Why UiPath and Workday’s Creators Had to Come Back — And Who’s Next
When AI threatens to eat your company, only the founder can rewrite the menu. There’s a moment in the life of every successful B2B company where the founder steps back and says: “I built this thing. It works. Let the professional operators take it from...
The Painful Gaps Between AI-Native and Traditional B2B Startups Today. Here’s a Checklist To Help. Which Are You … Really?
Anyone investing (including me) has been spending a lot of time with both AI-native startups and traditional B2B companies lately. We see what the newcomers are doing, what the hypergrowth players are doing, and how the incumbents are handling the AI Age. The...
The Agent Orchestration Problem: How We Wire 20+ AI Agents Together Without Losing Our Minds
Most of the AI agent content out there follows the same script: we deployed an AI SDR, here are the results, wasn’t that amazing. Nobody talks about what happens when you have multiple agents. When you have an AI SDR in Artisan, another one in Salesforce...
The Wave of AI Agent Churn To Come: Prompts Are Portable
I was in a board meeting last week for a breakout AI B2B leader at $100m+ ARR and the team was excited … but stressed. Why? So many of their largest customers were happy to sign relatively large checks for their AI Agent. Six figures. Some even seven. The product was...
AI Agents in Sales and Finance Aren’t Behind. They’re Just Next. The Latest Data from Anthropic and ~1,000,000 Tool Calls.
Anthropic just published a breakdown this week of where AI agents are actually deployed across nearly 1 million real production tool calls. Software engineering sits at 49.7%. Sales and CRM is at 4.3%. Finance at 4.0%. Legal at 0.9%. At first it might seem to say AI...
SaaS Isn’t Dead. But the Way You Used to Win in B2B? That’s Gone.
There’s been a massive SaaS sell-off since mid-2025. Multiples compressed. Growth stocks punished. The “SaaS is dead” takes are everywhere again. B2B isn’t dead. Software is still eating the world. Businesses still need tools. Enterprise...
Is SaaS Dead? No. But One Thing Is Clear: It’s Unstable.
For most of the past decade-plus, B2B software had a beautiful, almost boring stability to it. You’d build a product. You’d get it to $1M ARR. Then $10M. Then $100M. And the product you were selling at $100M ARR looked … pretty much the same as what you...
Founder SaaStr
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