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...
by Jason Lemkin | Sep 12, 2026 | Blog Posts, Leadership
Frank Slootman is the only CEO in history to take three enterprise software companies public. Data Domain, then ServiceNow, then Snowflake. At their peaks those three were worth more than $200 billion combined. He took ServiceNow from roughly $100M in revenue through...
by Jason Lemkin | Sep 11, 2026 | Blog Posts, Early, Fundraising, Leadership, Q&A |
Dear SaaStr: What is considered a fair or happy medium secondary amount for the founders to take off the table at a Series B VC funding round? Secondary sales done right truly align founders and the company and incent them to go long. See Brian Halligan’s (co-founder...
by Jason Lemkin | Sep 7, 2026 | Blog Posts, Leadership
I’m seeing more and more founders come back to run their pre-AI B2B companies. Not because the board panicked over a bad quarter. Because it’s The Last Stand. The pattern shows up at companies big enough to have a base that sustains them and not agentic...
by Jason Lemkin | Sep 3, 2026 | Blog Posts, Growth, Leadership, Sales |
There’s a set of questions I get asked all the time: Should you pay sales reps on renewals? Should you pay sales reps on upsells a long time down the road? Should you pay sales reps on … ? I am a huge proponent of paying sales professionals well. But for...
by Jason Lemkin | Sep 3, 2026 | Blog Posts, Career Growth & Advice, Early, Leadership, Other, Q&A |
Dear SaaStr: What Do You Have to Get Right in a Start-Up? So many folks I meet want to start a start-up. They have an idea they are passionate about. They’ve worked under a great CEO, and they’re ready — they think — to do it on their own...
by Jason Lemkin | Aug 30, 2026 | Early, Fundraising, Leadership, Q&A |
Dear SaaStr: Should I Send My Pitch Deck to Any VC Who Asks for One? Look every investor is different But for me at least, Send The Deck Don't fight it. Don't ask for 20 minutes first. Don't say it's better with a live demo first. Decks may seem...
by Jason Lemkin | Aug 26, 2026 | Blog Posts, Exit, Exit Strategy, Leadership, Q&A |
Dear SaaStr: Why Do Many Startup CEOs Quit After Their Companies Are Acquired? Five reasons: First, it’s very difficult for most founder-CEOs to work for someone else. They generally don’t mind working with others. They don’t even need to be “the boss”. But being told...