by Jason Lemkin | Jun 2, 2026 | Blog Posts, Early, Growth, Scale |
When you see Founder Mode from a non-founder When you find a VP, an exec, that actually cares as much as a founder, or almost as much … Promote them fast. ASAP. Double their equity. And … never let them go. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) May 29, 2026 It...
by Jason Lemkin | Jun 1, 2026 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
We’ll take four A+ specialized AI agents over one B+ all-in-one platform every time. At least … for now. We’ll take four A+ specialized AI agents over one B+ all-in-one platform every time. At least … for now. The all-in-one AI agent builders promise...
by Jason Lemkin | Jun 1, 2026 | 5 Interesting Things, Blog Posts, Scale
Entrata filed its S-1 on May 28 to list on the NYSE under the ticker “ENT.” It’s the multifamily property management Operating System out of Lehi, Utah, founded way back in 2003, with Silver Lake holding majority control since 2022. The numbers are...
by Jason Lemkin | Jun 1, 2026 | Blog Posts, Early, Hiring |
If a sales exec makes it anything but effortless to schedule a job interview with them, Basically it won't work out — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) February 13, 2024 So I remember years ago I went to hire my first VP ever. To make it even tougher,...
by Jason Lemkin | Jun 1, 2026 | Blog Posts, Sponsored Posts
Payroll compliance is a business where one wrong answer can cost $250,000. Papaya Global runs it across 160 countries, and they kept losing a quiet battle. At 2am, when a client has a real question, like whether they can terminate a worker in Germany, the client does...
by Jason Lemkin | May 31, 2026 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai, Sales
You’d assume Anthropic, of all companies, would be running on some self-grown, cutting-edge AI-native sales platform. Maybe a Salesforce killer they built themselves. Maybe Claude baked into the protocol layer of every workflow. They aren’t. At least not...
by Jason Lemkin | May 31, 2026 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
The Replit team came out in force to SaaStr AI 2026 (from the CEO to the CRO and the President!). They also in an unguarded moment interviewed me on stage and off stage about how we’re actually running SaaStr AI with our agents. The real, unglamorous,...
by Jason Lemkin | May 31, 2026 | Blog Posts, Career Growth & Advice, Growth, Q&A, Sales, Sales |
Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make? Let me just summarize my #1 observation here: the top mistake first-time sales managers make is recruiting. In that — they can’t do it. They can’t recruit great reps. They can recruit some mediocre...
by Jason Lemkin | May 30, 2026 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Agents Really > Humans in Many Cases. If the AI Agent is Really Well Trained and Designed. There’s a part of running AI agents in production that nobody writes about. It’s not the cost. It’s not the hallucinations. It’s not the setup....
by Jason Lemkin | May 30, 2026 | Blog Posts, Early, Sales, Sales |
I'd say about 66% of founders step back from sales when they hire a VP of Sales 95% of the time, it backfires You don't get that time back. You just use it in different parts of the sales process. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) May 27, 2026 So...
