Dear SaaStr: How Do You Draw The Line Between Founder and First Employee?
Dear SaaStr: How Do You Draw The Line Between Founder and First Employee? I’d suggest if you’re not sure where to draw the line … maybe don’t. It should be obvious. Founders are “there” before there is anything. Before a name. Before a product idea, usually. Before a...
Dear SaaStr: What is Your Best Advice for Maintaining Healthy Co-founder Relationships?
Dear SaaStr: What is Your Best Advice for Maintaining Healthy Co-founder Relationships? Talk. Dysfunctional co-founders don’t talk. Not for real. They stew. They get passive-aggressive. They email. They Slack. But they don’t talk. I don’t mean talk in group settings,...
Dear SaaStr: What Are The Traits That Define a Great VP?
Dear SaaStr: What Are The Traits That Define a Great VP? The difference between a Good, a Great, and a Mediocre VP: A Good VP Maintains Velocity in Their Functional Area. This is hard enough as it is. If you grew 100% last year, growing 100% again this year is more...
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 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...
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...
Dear SaaStr: What is Your Worst Memory as an Entrepreneur?
Dear SaaStr: What is Your Worst Memory as an Entrepreneur? Let me make a short list: Having a critical co-founder walk out the door and never return. This happened to me once with a true co-founder, and once with a critical early employee (a critical COO). The...
Dear SaaStr: What is The Biggest Difference Between Running a 10 Person Startup and a 100 Person Startup?
The biggest structural difference is you have to hire all the VPs by employee 50–100. You won’t be able to scale this far without a full management team — VPs of Sales, Marketing, Product, Engineering, Customer Success at least. But the toughest personal challenge for...
Dear SaaStr: How Bad Does it Look to Be on The Product Team at a Failed Startup?
Dear SaaStr: How Bad Does it Look to Be on The Product Team at a Failed Startup? If the company actually shipped a strong product people respect — not bad at all. If the company shipped something cr*ppy, a POS hack that looks like it — it’s a...
Dear SaaStr: What Are The Biggest Problems You Face as a Startup Founder?
Dear SaaStr: What Are The Biggest Problems You Face as a Startup Founder? The list of problems is endless (this is one of the hardest parts of the job), but let me try to order a few of the biggest challenges roughly based on stage: Top issues you face as a startup,...
Dear SaaStr: What Were Your Toughest Times Before Breaking Out?
Dear SaaStr: What Were Your Toughest Times Before Breaking Out? My toughest times: COO pulling out after signed term sheet — VCs then pulled term sheet. This of course was my fault — I hired the “wrong” COO. But boy it was tough. I had 9 employees on payroll and $0 in...
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