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...
A few bits of advice you hear a lot in SaaS — especially from VCs and on social media — that I think often don’t really work in practice: “Move to annual contracts to generate more cash.” Sure, if customers want to pay annually for a discount —...
Dear SaaStr: What is The Strangest Thing You Have Learned About Entrepreneurship? To me the “strangest” thing I learned is that you get pretty good around Year 3–4. Almost automatically. And somewhere around Year 5 at least, if you make it that long — you know exactly...
If you make the VCs pay a crazy high price, but you crush the numbers the next 90 days, no one remembers If you make the VCs pay a crazy high price, and you miss the next few months, no one ever forgets — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) November 19, 2025...
Top SaaStr Posts of the Week: #1. The SaaS Era of 2013-2022 is Over. Welcome to The World of Hyperfunctional SaaS. #2. ChurnZero: 38% More Customer Success Departments Are Reporting to the CRO. FBOW. | #3. 7 Things I Learned from Loren Padelford, CRO of $100m+ ARR...
Dear SaaStr: Why did Jason M. Lemkin Change his Point of View on The Value of a COO for Earlier Stage Startups? I try to work with (and invest in) CEOs that are better than me. I found, when I was a SaaS CEO, that the CEOs that complained about needing a COO early,...
We’ve talked a lot on SaaStr about the challenges in getting from nothing to that first $1m-$1.5m in ARR, “Initial Traction”. That it takes longer than you think. That if you get 10 customers, you can get another 10, 100, and so on. There’s a...
So I’m a little worried for Downtown Palo Alto Lytton Park has recently become overwhelmed with homeless and marijuana is everywhere in the air Blue Bottle and Hana House closed No one has still taken the old Apple Store or much of the Palantir space, Vans + retail...
Dear SaaStr: Why Are Buyers Not Ready to Spend Big on Acquisitions as Readily Today as in the Past? In tech at least, there are two big issues: #1. Revenues Multiples Are Down Even the best public SaaS companies are worth ~10x revenue today. In 2021, they were often...
So Ramp has its latest Top SaaS Vendors on Ramp report out for October 2024. Ramp covers a ton of spend but it is fairly tech focused in its customer base, so there’s a bit of a bias in what they buy there. But no matter what, it shows what its customers are...
