Dear SaaStr: At What ACV Can We Afford a Sales Team?
Dear SaaStr: At What ACV Can We Afford a Sales Team? The short answer hasn’t changed much: it’s still tough to afford a human sales team below $299 a month / $3k a year ACV. At least in the U.S. and Western Europe. The math just doesn’t bend enough....
Dear SaaStr: What Are The Biggest Lessons You’ve Learned from Failure as an Entrepreneur?
Dear SaaStr: What Are The Biggest Lessons You’ve Learned from Failure as an Entrepreneur? Don’t Fail. I’ve almost failed several times. Really almost every time. But never actually failed. Why not? Never quit. You can’t fail if you don’t quit. Find...
PE Is No Longer Coming to the Rescue. And That Probably Means No One Will.
M&A hit record highs last year. But like so many things in the AI Age, the benefits were not evenly distributed. For Plain Vanilla SaaS? PE has checked out. There’s a tough topic that it’s time to be honest about in 2026: PE is no longer coming to the...
Dear SaaStr: Can A SaaS Startup Really Scale With 2 Co-CEOs?
Dear SaaStr: Can A SaaS Startup Really Scale With 2 Co-CEOs? Many will tell you it’s a bad idea, and it probably is — in most cases. I sort of tried this myself, and it didn’t quite work. We had all the classic problems of unclear authority, especially...
Dear SaaStr: How Many Of Our Prospects and Customers Should I Meet Face-to-Face?
Dear SaaStr: Should an early- stage B2B startup meet every customer face-to-face to receive feedback? If you could — all of them. The more customers you meet in person, the more that buy from you, and the more “more stuff” they buy from you after,. The full data here...
The Trade Desk Was Priced for Perfection. Then Growth Slowed. Now It’s the Worst Performing Stock in the S&P 500.
The Trade Desk was the darling of adtech. A profitable, founder-led adtech software company that grew at epic rates year after year, built the leading independent demand-side platform, and positioned itself as the Switzerland of programmatic advertising. And then it...
Dear SaaStr: What Are Some of the Qualities of a “Bad” Startup CEO?
Dear SaaStr: What are some qualities of a bad startup CEO/founder in Silicon Valley? A few that I’ve seen across the handful of investments I’ve made … that didn’t work out: Not really committed to going long. This doesn’t so much make you a “bad” CEO as one that...
20VC x SaaStr Are Back: If Figma Isn’t Good Enough, What Hope Is There? Plus OpenAI Ads, Elon vs. Sam, and the $9B Replit Bet
With Harry Stebbings, Jason Lemkin, and Rory O’Driscoll If Figma—one of the best products in SaaS history—can’t sustain its IPO price, what does that mean for the rest of us? That’s the question that kicked off this week’s episode, and it led...
Should You Pay Reps More For Deals They Hunt Themselves? Sometimes. Here’s When.
Dear SaaStr: Should sales reps be compensated differently based on how much prospecting they do? For example, if all of their leads come inbound (without effort on their part) should they receive a lesser % per deal vs a rep that prospects for their own leads? It...
Dear SaaStr: Should We Pay Our Sales Reps on Renewals?
Dear SaaStr: Should We Pay Our Sales Reps on Renewals? Simple answer: most don’t. You can, especially in the early days. But very few SaaS companies pay sales reps on renewals as they scale. And you can definitely pay on upsells and account expansion. Longer...
Should You Hire a Sales Rep First, Or a Sales Manager?
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,...
20VC x SaaStr This Week: Anthropic at $350B, OpenAI’s Existential Risk, and Why a16z’s $15B Fund Actually Makes Mathematical Sense
A deep dive into the biggest AI rounds, the future of venture capital, and why California’s wealth tax could trigger a founder exodus We just wrapped another 20VC + SaaStr pod with Harry Stebbings and Rory O’Driscoll from Scale Venture Partners, and this...
Dear SaaStr: What Happens if a VC Loses All Their Money on an Investment?
Dear SaaStr: What Happens if a VC Loses All Their Money on an Investment? It’s OK — if it’s not too much. As long as the founders did everything they possibly could to make it work. Everything. And were honest. There are two types of losses for VCs...
Dear SaaStr: How Do You Deal With an Unreliable Co-Founder?
Dear SaaStr: How Do You Deal With an Unreliable Co-Founder? You first try to move them into an individual contributor role. If that doesn’t work, then move them out. This is one of the most frustrating outcomes, when a very talented co-founder becomes “unrealiable”....
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