by Jason Lemkin | Oct 18, 2026 | Blog Posts
The SaaStr-side lessons from Valar, Jev, Haiku 5.5, Airtable and the Decacorn boom #1. Got cut out of a round? Say it once, then drop it. Years ago I was the only investor in a company for years. I bridged it when no one else would and helped wherever I could. Then a...
by Jason Lemkin | Oct 18, 2026 | Blog Posts |
49.7% of execs changed jobs in the last 16 months. 63% of CMOs turned over, says Jason Lemkin. "We have to constantly enrich our data because our buyers… turn over so fast that they're usually not there by the next." Your champion is already gone....
by Jason Lemkin | Oct 18, 2026 | Blog Posts, Early, Growth, Hiring, Q&A |
Dear SaaStr: What Role Do Founders Play Once They Hire an Outside CEO? Let me take a slightly different take on the question. Maybe you are really asking – “Am I still on the hook if we hire a ‘real’ CEO to run the company? ‘Cause...
by Jason Lemkin | Oct 17, 2026 | Blog Posts
Bending Spoons just announced most of the Airtable team will be laid off, explaining that small teams ship more and better. He pointed to a new Core team that has shipped 30+ top customer requests in 3 weeks, plus new Performance and Infra teams. Today we’re laying...
by Jason Lemkin | Oct 17, 2026 | Blog Posts |
63% of CMOs changed jobs in the last 16 months. "Half of people changed jobs in 16 months. But CMOs changed at a much higher rate: 63%," says Amelia. Your champion is gone by next SaaStr Annual. pic.twitter.com/a8T9yRb0lg — SaaStr.ai (@saastr) October...
by Jason Lemkin | Oct 17, 2026 | Blog Posts, Q&A |
Dear SaaStr: Once Your Equity Vests In a Startup … Why Stick Around? It’s an interesting and subtle question, especially these days in the Bay Area, where many barely stay 1 year to their cliff, let alone the full 4–5 years to vest. Even employees at OpenAI...
by Jason Lemkin | Oct 16, 2026 | Artificial Intelligence (AI), Blog Posts, Featured Podcasts, Podcasts, SaaStr.Ai, Vibe Coding
Amelia and I just published Episode #016 of The Agents. Same setup as always: three humans, 21+ agents in production, and a B2B + AI business on track for about $20M this year. This week we went deep on truly going “headless” and agent-first with your...
by Jason Lemkin | Oct 16, 2026 | Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
G2 surveyed 1,019 B2B decision-makers in July 2026 for its 2026 AI Agents Insight Report. The most valuable data for founders is on pricing and renewals. 86% of B2B software buyers say their company bought AI agent software or services in the past year, up from 69% in...
by Jason Lemkin | Oct 16, 2026 | Blog Posts, Q&A |
Dear SaaStr: What Can I Do To Increase My Win Rates? Two years ago, the answer to this question was mostly sales execution. Hire a better VP of Sales, train on competition, run a real bake-off, review your lost deals. All of that still matters. But three things...
by Jason Lemkin | Oct 15, 2026 | Blog Posts
Pro rata goes to Delaware, Nvidia circles Reflection, a record 42 decacorns, and why the B2B apocalypse never ended for anyone under $1B in ARR A nuclear startup took its earliest institutional backer to court over a spring-back clause. Meta put its first model at the...
by Jason Lemkin | Oct 15, 2026 | 5 Interesting Things, Blog Posts, Scale
Bending Spoons is worth about $34 billion. It buys B2B companies at 2.3x to 2.7x ARR. Since August it has paid 2.7x ARR for Airtable and 2.3x for Miro. That is $1.08 billion of ARR for $2.64 billion of enterprise value, signed 37 days apart. Its own stock trades at...
by Jason Lemkin | Oct 15, 2026 | Blog Posts, Fundraising |
Don’t get triggered by VCs ghosting you -> It’s just your answer And if you aren’t sure, just send a check-in email a few days later https://t.co/cJX8lihtrQ — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) October 14, 2026 One of the most frustrating things for...
by Jason Lemkin | Oct 15, 2026 | Blog Posts, Q&A |
Dear SaaStr: Growth Has Slowed and My VP of Sales is Pushing Me To Hire More Reps. Is That The Right Way to Go? No. Not 9+ times out of 10. Probably 9.8 times out of 10. It’s a desperation move. In fact, the #1 sign your CRO / VP of Sales is really struggling is...
by Jason Lemkin | Oct 14, 2026 | Blog Posts, Sales
Want to steal a customer from your competitor? 99% of sales reps, 95% of CROs, and 99% of CEOs never ask the one question that would get it done. And it’s so, so simple: “What would it take for you to move over to us? What problem could we completely, 100%...
by Jason Lemkin | Oct 14, 2026 | Blog Posts, Growth, Hiring, Sales |
You just can't hire a VP of Sales that hasn't themselves hired a few great reps before At least 2 good sales reps before, that hit or exceeded quotas pic.twitter.com/8f0qiUVPxV — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) February 10, 2024 We’ve talked a...