by Jason Lemkin | May 29, 2026 | Blog Posts
The final day at SaaStr AI Annual was our agent stack deep dive day. Amelia and I walked through the 20+ agents we run our business on. Adam Guild from Owner.com showed how they crossed $100M ARR by going all-in on AI three years ago. Andrew Bialecki from Klaviyo...
by Jason Lemkin | May 29, 2026 | 5 Interesting Things, Blog Posts, Scale
Reaccelerating growth at scale is the hardest thing in B2B. Almost no one does it. The law of large numbers is tough to defeat: the bigger you get, the more new revenue you need just to hold the same growth rate, and eventually the math wins. HubSpot, Workday, even...
by Jason Lemkin | May 29, 2026 | Blog Posts, Early, Q&A, Sales |
Dear SaaStr: Can salespeople really get customers to buy a product they don’t need right now? Yes, at least up to a point. In many ways, getting folks to buy a product they don’t truly need today is the true art of sales. If they really, truly needed it right...
by Jason Lemkin | May 28, 2026 | Blog Posts
We did the 20VC x SaaStr episode this week with Harry Stebbings and Rory O’Driscoll, and by the end something funny happened. Every single segment, no matter where we started, collapsed into the same question: What is the right split between humans and tokens,...
by Jason Lemkin | May 28, 2026 | Blog Posts, Marketing
Yeah. I never blocked any domains or people pre-AI … but now … every day The rotation and throway does get around it partially though I am surprised the lame PR apps don’t use them — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) May 27, 2026 For the past 12+ months, we...
by Jason Lemkin | May 28, 2026 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Gartner released its updated worldwide AI spending forecast last week. And per their latest data, AI software spend is … breathtaking: AI Software spending is growing to $453 billion in 2026. Up 60% YoY. And on pace for $638 billion in 2027. That’s the...
by Jason Lemkin | May 28, 2026 | Blog Posts, Q&A, Sales |
Dear SaaStr: How Do The Best Sales Leaders Retain Their High Performers? A few ways I’ve observed that the best sales leaders retain the best: They promote the best. You can’t promote everyone, but you can almost always promote your best. The fastest you...
by Jason Lemkin | May 27, 2026 | 5 Interesting Things, Blog Posts, Scale
Guess whose stock Is up +66% year-to-date? And trades at 20x ARR? In the midst of the most challenging run for software stocks … ever? Datadog. As of May 22, 2026: $222.32 per share, +66.20% year-to-date. Market cap: $79B. 52-week low was $98.01 just months...
by Jason Lemkin | May 27, 2026 | Blog Posts, Scale
An end of an era Of my generation of SaaS CEOs, no star burned brighter than Dropbox It grew to $1B ARR faster than any before, and burning almost nothing, perfecting the PLG motion. The startup we all wished we founded. But in the end, there was no second act even...
by Jason Lemkin | May 27, 2026 | Blog Posts, Early, Sales, Sales |
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...
