Dear SaaStr: What does a US-Based SaaS company Need to Know Before Expanding into Europe?
Dear SaaStr: What does a US-Based SaaS company Need to Know Before Expanding into Europe? Let me simplify it all to 4 simple pieces of advice: For most U.S. companies: Start marketing, supporting and talking to European customers as a distinct segment once you have 10...
My Startup Doesn’t Have a Free Trial or Freemium Option. Should We Change This?
Dear SaaStr: My Startup Doesn’t Have a Free Trial or Freemium Option. We require payment right away. Should we change this? Free trials and freemium options work well — if you can support them well. Ask yourself: Can someone deploy your app in minutes? If they...
Dear SaaStr: What Mistakes Did You Make When Starting Your Business That, In Retrospect, You’re Glad You Made?
Dear SaaStr: What Mistakes Did You Make When Starting Your Business That, In Retrospect, You’re Glad You Made? I think some of my biggest mistakes, at the time I made them, I had to make them to survive. Still, they were terrible mistakes 🙂 My list: Launching...
Dear SaaStr: Who Should Our First Head of Customer Success Report To?
Dear SaaStr: Who Should Our First Head of Customer Success Report To? Ah, who should Customer Success report to. It’s not super simple. There are generally 3 options in the early and middle days: CEO. VP of Sales (once you have one) and/or later, CRO once you add one....
Dear SaaStr: Why Do So Many SaaS CEOs Get Fired?
Dear SaaStr: Why Do So Many SaaS CEOs Get Fired? I think this is a bit of a misnomer. I’ve been investing for 10 years, across multiple billion+ outcomes, and only seen 1 founder “fired” in my portfolio, and one who the biggest VC suggested they step down. And even...
Dear SaaStr: What Are The Worst Realities of Being An Entrepreneur?
Dear SaaStr: What Are The Worst Realities of Being An Entrepreneur? The worst reality, which is also part of what makes entrepreneurship so visceral — is the true feeling of Failing With 100% Responsibility. It often doesn’t leave you until $20m, $30m ARR, or...
Dear SaaStr: Does It Always Make Sense to Say “No” to a Custom Feature If We Have Mid-Market (ACV 20k to 50k+) Customers?
Dear SaaStr: Does It Always Make Sense to Say “No” to a Custom Feature If We Have Mid-Market (ACV 20k to 50k+) Customers? No. This is not wise advice, it is bad advice in many cases. As long as the deal size is big enough. If a potential deal, is >...
My Top 8 Mistakes Investing in SaaS Startups
Dear SaaStr: What are some of the most costly mistakes done by novice investors? The #1 rule never to bend in startup investing: Never invest in a founder that isn’t better than you When I look back, this is really the only reason I’ve lost money — Jason ✨Be...
Annual or Monthly Payments for SMBs? Data from Zoom, Freshworks, Expensify, Squarespace, and More
Dear SaaStr: What is the average percentage of annual vs. monthly plan sold for a BtoB SaaS startup targeting the SMB market? Here are some rough-and-tough numbers: If the customers are so small they are basically paying out of their own pockets … then 80%+-...
Dear SaaStr: My Top Sales Rep Made $600,000 a Year — And Just Quit! What Happened?
Dear SaaStr: My Top Sales Rep Made $600,000 a Year — And Just Quit! What Happened? Ok to some of you this will make no sense. But now I’ve seen this happen again and again, including just the other day at one of my top portfolio companies. The #1 or #2...
Dear SaaStr: How do VCs Really Feel About Founder Salaries? I Was Told That a General Rule of Thumb is 75% of Market
Dear SaaStr: How do VCs Really Feel About Founder Salaries? I Was Told That a General Rule of Thumb is 75% of Market The 75% Rule once you are VC Funded for more than a few million dollars is a good one. But if you raise less than that — 75% may well be too...
Dear SaaStr: Why Do Many Startup CEOs Quit After Their Companies Are Acquired?
Dear SaaStr: Why Do Many Startup CEOs Quit After Their Companies Are Acquired? Five reasons: First, it’s very difficult for most founder-CEOs to work for someone else. They generally don’t mind working with others. They don’t even need to be “the boss”. But being told...
Dear SaaStr: What Hours Do SaaS Sales Reps Work?
Dear SaaStr: What Hours Do SaaS Sales Reps Work? It really varies in SaaS. Sales is hard. It’s a lot of Nos. A lot of pushback. A number you can’t hide from, and you have hit, every month, every quarter, every year. But … but … if you are really good at sales,...
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...
Founder SaaStr
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