by Jason Lemkin | Nov 10, 2026 | Blog Posts, Growth, Leadership, Q&A, Sales |
Dear SaaStr: How Do You Respond to a Prospect That Sees You As An “Acquisition Risk”? “Acquisition risk” is a subset of a whole category of “vendor risk”. Until you IPO, or are the de facto leader over many years, Big Cos are always going to look at...
by Jason Lemkin | Oct 21, 2026 | Blog Posts, Fundraising, Leadership
VCs have always checked out when founders stop sending investor updates But today I think even more so The opportunity cost of investing time in a startup that can't be the next Cursor is high If you don't even get monthly updates anymore, well, you just write...
by Jason Lemkin | Oct 13, 2026 | Blog Posts, Leadership
Every time I see a CRO that doesn't sell themselves, they fail. Every time I see a CTO that doesn't code themselves, they fail. Every time I see a CMO that doesn't market themselves, they fail. Every time I see a CCO that isn't constantly meeting with...
by Jason Lemkin | Oct 7, 2026 | Blog Posts, Career Growth & Advice, Early, Leadership, Q&A |
Dear SaaStr: My Co-Founder is Threatening to Quit Unless I Give Him More Equity; what should I do? Generally, this is the last, best chance to fix things. Founder equity splits are a tough thing. What seems fair on Day 0 may seem less fair on Day 720. The one that...
by Jason Lemkin | Oct 2, 2026 | Blog Posts, Fundraising, Leadership |
Dear SaaStr: How Can I Make Sure My Board Doesn’t Fire Me? Founders are often guarded toward most VCs. Perhaps they should be. That’s a different, and longer conversation. And one thing founders tend to worry about is — can I be fired by my...
by Jason Lemkin | Sep 28, 2026 | Blog Posts, Growth, Leadership, Sales |
I've never seen a great VP of Sales hide from a miss — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) August 26, 2023 We’ve talked a lot on SaaStr over the years about how to hire a great VP of Sales — and how to course-correct if you’ve made a mis-hire. The two...
by Jason Lemkin | Sep 27, 2026 | Blog Posts, Human Resources, Leadership
There’s one thing you will look back on regret: letting one of those truly Irreplaceable folks on your team … leave. Mainly it happens as you scale. Things chance. You need larger teams, different processes. And you bring in new executives that maybe don’t seem them...
by Jason Lemkin | Sep 25, 2026 | Blog Posts, Customer Success, Growth, Hiring, Leadership, Q&A |
Dear SaaStr: How Do We Close Bigger Deals? If you already have a few bigger deals under your belt, but most are smaller … a few higher-level suggestions: #1. Hire a Very Good CRO / VP of Sales that has sold at your “high end” price point. They will be much better at...
by Jason Lemkin | Sep 24, 2026 | Compensation, Fundraising, Growth, Leadership, Q&A |
Dear SaaStr: When My Startup Raises $10m, Would It Be Appropriate to Take a $170k Salary (no co founders)? Yes, not a problem. You should take a “market correct” salary as soon as it’s economically immaterial to the company. I don’t write $10m...
by Jason Lemkin | Sep 22, 2026 | Blog Posts, Leadership
I’ve seen it again and again across 30+ investments, 10+ unicorns, and hundreds of portfolio company board meetings. There’s one pattern that predicts VP failure better than anything else I’ve seen. Not their resume. Not their pedigree. Not even...
by Jason Lemkin | Sep 21, 2026 | Blog Posts, Leadership
So there’s a new option for seasoned B2B execs now: join something growing … 0%. Ok maybe 0%-10%, let’s call it. This sounds a little wacky described as a career choice. But it’s something some execs have always quietly done, and there are more and...
by Jason Lemkin | Sep 21, 2026 | Blog Posts, Growth, Leadership, Sales, Sales |
We’ve talked a ton on SaaStr over the years on how to make sure your CRO / VP of Sales and top hires really work out. That they are the right ones. We can pretty much summarize a lot of it into the following: Your VP of Sales should have lots of experience...
by Jason Lemkin | Sep 19, 2026 | Blog Posts, Featured Posts, Growth, Leadership |
Recently I put together a quick list on Twitter of the Top 10 things that with hindsight, I could and should have done to get from $1m to $10m ARR faster — and with less stress. I thought it would be worth drilling down deeper into each of them and sharing the...
by Jason Lemkin | Sep 18, 2026 | Blog Posts, Compensation, Early, Fundraising, Leadership, Q&A |
Dear SaaStr: How do VCs Really Feel About Founder Salaries? I Was Told That a General Rule of Thumb is 75% of Market The 75% Rule once you are VC Funded for more than a few million dollars is a good one. But if you raise less than that — 75% may well be too...
by Jason Lemkin | Sep 16, 2026 | Blog Posts, Fundraising, Leadership |
I was catching up with a VC friend the other day and asked him about a company I’d referred to him. They’d passed on the investment (which is of course fine), despite the company meeting basically every investment criteria I knew about the firm. I asked...