Dear SaaStr: What’s the Best Way to Follow Up With a Prospect That Says “I’ll Get Back to You” Let’s start with honesty: “I’ll get back to you” almost always means No — or at best, Not Now. That’s not cynicism....
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...
Dear SaaStr: How Can I Become a Better VP of Sales? The hard truth: most VPs of Sales fail not because they can’t sell, but because they don’t understand what the job actually is. It’s not managing a team. It’s not building process decks....
Every week, Harry, Rory, and Jason sit down together to break down the biggest stories in AI and B2B. Anthropic picks a fight with the Pentagon and loses. At least for the moment. OpenAI closes $110 billion privately — four times the size of the largest IPO in...
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...
CrowdStrike at $5.25B ARR just posted its largest quarter of net new ARR ever — $331M, up 47% year-over-year. The first pure-play cybersecurity company to cross $5B in ARR. The first year ever above $1B in net new ARR. Record operating income, record free cash flow,...
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...
Dear SaaStr: I made it to the final round for an SDR position at a leading vertical B2B company. The interview is with the Sales Manager. How do I prepare so I actually get this offer? First off — congrats. Making it to a final round SDR interview at a real vertical...
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...
I want to share something about the founder journey that may surprise many of you. I sold my last startup over a decade (!) ago. And … I’m still tired. What do I mean? I sold my second startup to Adobe waaaay back in 2011. That’s quite a long time...
