by Jason Lemkin | Nov 2, 2026 | Blog Posts, Company Culture, Fundraising, Growth, Human Resources, Q&A |
Dear SaaStr: Do VCs Want To Talk To Senior Execs That Quit a Portfolio Company? Sort of. Maybe. Generally, if the issues are around: harassment or any inappropriate conduct, or fraud or misleading financials, etc, or something else that is wrong legally, ethically,...
by Jason Lemkin | Nov 1, 2026 | Blog Posts, Q&A |
Dear SaaStr: How Do I Find Product Market Fit In the Early Days? Find a little bit of it first ;). Just a little bit. And then relentless build on top of that. Finding product-market fit is the single most important milestone for any startup. Without it, nothing else...
by Jason Lemkin | Oct 30, 2026 | Blog Posts, Compensation, Hiring, Q&A, Sales, Scale |
Dear SaaStr: What Sales Comp Plan Should I Use For Our Very First Sales Rep? At the end of the day you have to solve for two things: A plan that gives the reps a living, fair wage; and A plan that you know and feel is accretive to the company. Sales reps have to be...
by Jason Lemkin | Oct 29, 2026 | Blog Posts, Growth, Hiring, Human Resources, Q&A |
Dear SaaStr: What Were The First Five Hires You Made After Product-Market Fit? My first 5 hires at Adobe Sign / EchoSign, beyond the core founding+ team, once we had paying customers and first, if early, product-marketing fit: #1: Full-time sales rep at $8k-ish MRR....
by Jason Lemkin | Oct 28, 2026 | Blog Posts, Q&A |
Dear SaaStr: How Do I Know If My New VP of Marketing Is Going To Make It? You’ll know pretty quickly if a new VP of Marketing is going to make it, or not. The best ones deliver real results fast, and there are clear signs to watch for in the first 30-90 days....
by Jason Lemkin | Oct 27, 2026 | Blog Posts, Growth, Q&A, Sales |
Dear SaaStr: How Many Sales Reps Do I Need? More than you probably would think. You can back into how many sales reps you’ll need in SaaS: First, figure out how much sales-driven revenue you need to close in the next twelve months. Because that’s more than now....
by Jason Lemkin | Oct 26, 2026 | Blog Posts, Early, Q&A, Sales |
Dear SaaStr: Should I Hire a Sales Rep First, Or a Sales Manager First? The ideal flow is: You (founder-CEO) close the first batch of customers, say the first 10 or 20. If you don’t, you’ll never really know how it’s done. Or be able to help anyone else, really. Then,...
by Jason Lemkin | Oct 25, 2026 | Blog Posts, Early, Q&A, Sales |
Dear SaaStr: What qualities do the great salespeople have? When I'm ready to buy, A great sales rep makes it easier. And better. And gets all my questions answered. A mediocre rep just makes it harder. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) April 2, 2022 I...
by Jason Lemkin | Oct 24, 2026 | Blog Posts, Early, Q&A |
Dear SaaStr: As a Co-Founder, When Do You Know It’s Time to Quit? You don’t. Why? Because 50% or more of the time, it’s because you are tired. And when you’re tired, you don’t always make the right decisions. Before you quit: Talk to 2–3 mentors you trust. See...
by Jason Lemkin | Oct 23, 2026 | Blog Posts, Exit Strategy, Q&A |
Dear SaaStr: How Do You Know When It’s Time to Sell Your Startup? First off, the axiom that companies are bought, not sold, is mostly right. 95 times out of 100, you can’t wake up some morning and just go sell your start-up. Unless there are pre-existing...
by Jason Lemkin | Oct 22, 2026 | Blog Posts, Q&A, Sales
Dear SaaStr: What is the Difference Between a Good Sales Exec and a Great One? A good rep hits quota. A great rep closes multiples of what the good one does, on the same leads, and the gap almost always comes down to the same handful of things: The gap is bigger than...
by Jason Lemkin | Oct 21, 2026 | Blog Posts, Q&A |
Dear SaaStr: I just sold my business for $130M, and now I’m debating whether or not to stick around. First off, congrats on the $130M exit—that’s a huge milestone. Selling a business is a massive achievement, but deciding whether to stay or leave...
by Jason Lemkin | Oct 20, 2026 | Blog Posts, Growth, Q&A |
Dear SaaStr: As a Founder, When Did You Realize You Were Limiting Your Company’s Growth and Success? As we approached $10m ARR, we were doing very well: growing 100%, cash-flow positive, with 100%+ NRR. But I did see that certain of my weaknesses still were...
by Jason Lemkin | Oct 19, 2026 | Blog Posts, Q&A |
Dear SaaStr: How Can You Land Big Customers If You’re a New Startup No One Has Heard Of? Solve one of their top pain points, for real — that no other vendor is solving. And do it in a way that isn’t super risky. If you haven’t sold to the F500 / Global 2000...
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...