How to Handle, and Share, Bad News
Run toward bad news Sometimes you need a moment. That's OK. But after that, hiding makes it worse. Process it … Then: Address itShare itTalk about itMake a planAct on it Your team and investors will rally — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin...
6 Key Signs a VP of Sales Can’t Scale Beyond $5m-$10m ARR
The best VPs can recruit in ways I barely understand You need someone for a key role? They somehow have 2-3 strong candidates in a week or two This is so, so hard But the very best VPs make it somehow look almost effortless It's also the only way to scale —...
VPs That Can’t Hire … They Aren’t Real VPs. At Least, Not Yet.
The best VPs can recruit in ways I barely understand You need someone for a key role? They somehow have 2-3 strong candidates in a week or two This is so, so hard But the very best VPs make it somehow look almost effortless It's also the only way to scale —...
Dear SaaStr: Is it True VCs Don’t Like to Invest Where Founders’ Equity is Fully Vested?
Dear SaaStr: Is it True VCs Don’t Like to Invest Where Founders’ Equity is Fully Vested? Yes, it’s true but … #1. VCs Are Less Rigid Here Than They Used To Be If a deal is hot and you have multiple offers, VCs won’t push as hard here as...
A Simple Commitment Test For You And Your Co-Founders (Updated)
As we’ve talked about before, the great thing about SaaS is it compounds. Once you have something, it builds on itself. But it takes time. It takes 7-10 years to build something real. And probably 20 years to build something for the ages in SaaS. If all...
Dear SaaStr: What Are The Unspoken Downsides of Being a VC or Angel Investor?
Dear SaaStr: What Are The Unspoken Downsides of Being a VC or Angel Investor? Look the downsides are small folks. As a founder, you are often days away from total failure. This basically never happens for VCs, and even when it does, it happens over a decade+ (life of...
Dear SaaStr: What Are Great Examples of Fast Follower Companies That Become Market Leaders?
Dear SaaStr: What Are Great Examples of Fast Follower Companies That Become Market Leaders? In many ways, All of Them. Microsoft. Bought 86-DOS, turned into MS-DOS (which Gates did not invent), which in turn was an improved clone of CP/M. Did not invent BASIC, either....
Dear SaaStr: What’s The Hardest Part About SaaS Companies, At Each Stage?
Dear SaaStr: What’s the Harder Part About SaaS Companies, At Each Stage? The hardest part changes every 12–24 months, and the whole company changes every 30-36 months or so. But a few thoughts on “the hardest part” for the first few stages: From $1-$100k in...
Dear SaaStr: Should SaaS Startups Really Have CROs or COOs? Is That Too Many Management Layers?
Dear SaaStr: Should SaaS Startups Really Have CROs or COOs? Is That Too Many Management Layers? A few years ago, I would have said No. There’s no way a SaaS startup needs a “CRO” or “COO” or other C-level Officers Without a Clear, Single Functional Area to Own Until...
A Few VP of Sales / CRO Personas to Stay Far Away From
We’ve talked a ton about How to Hire a Great VP of Sales on SaaStr, but I wanted to highlight a few VP of Sales / CRO “personas” that I rarely, if ever, see work out. Because again and again, many of you will hire this VP of Sales / CRO. So many...
Dear SaaStr: What’s a Good Example of a Monthly Investor Update?
Dear SaaStr: What’s a Good Example of a Monthly Investor Update? The #1 key: design a template that is simple enough you can send it out on the first of the month, every month. That way you will actually get it done. Beyond that, in SaaS, I love a short update...
Dear SaaStr: What Should I Do if My Co-founder is a Complete Jerk?
Dear SaaStr: What Should I Do if My Co-founder is a Complete Jerk? It if’s that bad — it’s just not going to work. The issue isn’t so much that he’s a complete jerk. Maybe he is, maybe he isn’t, or most likely, it’s somewhere in the...
Going Long: How Procore’s Founder and CEO Tooey Courtemanche Built a Billon-Dollar SaaS Empire Over 23 Years
Tooey Courtemanche, CEO and Founder of Procore, shared insights into his 23-year journey. From surviving economic downturns to scaling into a multi-product enterprise serving millions, Procore’s story is a masterclass in vertical SaaS excellence.
Dear SaaStr: What Causes Co-Founder Breakups?
Dear SaaStr: What Causes Co-Founder Breakups? Yes. I’ve had one, and watched several. It’s really tough to go through. The root cause for mine, and most of the ones I’ve observed, is disalignment on goals and outcomes: Do you want to IPO, but your cofounder would be...
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