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...
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...
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: Do SaaS Companies Typically Pay Their Sales Reps a Bonus on Renewals? If So, How Much is Typical?
Dear SaaStr: Do SaaS Companies Typically Pay Their Sales Reps a Bonus on Renewals? If So, How Much is Typical? Simple answer: almost no SaaS companies pay sales reps on standard renewals. Longer reason: they don’t — because you want to specialize. We’ve all learned...
Dear SaaStr: What Are The Best Strategies for Raising Capital if Your Goal is To Get Acquired?
Dear SaaStr: What Are The Best Strategies for Raising Capital if Your Goal is To Get Acquired? Well, first, let’s be clear — it’s tough if your core goal is to get acquired for a big price in most cases. There really aren’t that many good...
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 Are The Biggest Challenges For a Non-Technical Founder?
Adding enough value in the beginning. If you can’t build it, can you: Sell it? That’s worth it. If you can bring in all the first customers, that’s a magical skill. Design it? Head of Product is just as important as Head of Writing Software. Sometimes, one person can...
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: 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,...
The #1 Worst Hire of All When You Are Just Starting To Scale: The Mediocre VP of Engineering
Every time I see a CRO that doesn't sell themselves, they fail. Every time I see a CTO that doesn't code themselves, they fail. Every time I see a CMO that doesn't market themselves, they fail. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) November 28, 2024...
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...
The Double-Stretch VP Rarely Works Out
"Too many top sales reps want to be a VP. But management isn't for them. It's such a different skill set in sales." @lennysan + me pic.twitter.com/24qbcjbh9k — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) July 10, 2024 Over the past...
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