Dear SaaStr: Should I Call Myself a Owner, Founder, or CEO?
Dear SaaStr: Should I Call Myself a Owner, Founder, or CEO? CEO. Although, perhaps say it in a neutral tone, with no bravado. I always thought the title was a bit silly when running tiny start-ups. But I missed an important point: Customers, Prospects, Recruits and...
Dear SaaStr: Why Are So Many CEOs Former Engineers, or At Least Have Technical Backgrounds?
Dear SaaStr: Why Are So Many CEOs Former Engineers, or At Least Have Technical Backgrounds? I’ve come to almost exclusively invest in founder-CEOs that are engineers. Or at least where the co-founder CTO is a true equal partner to the CEO. Why? Well to get something...
Hitting Hypergrowth: How To Take Your SaaS Company from $25M to $100M and Beyond with Amplitude’s CEO, Spenser Skates
Discover four critical lessons for maintaining hypergrowth on your journey from nothing to $100M and beyond with the CEO and co-founder of Amplitude.
Dear SaaStr: What Has Been Your Biggest Career Mistake?
Dear SaaStr: What Has Been Your Biggest Career Mistake? Maybe not slowing down just a little bit. The week in my first real professional job when I realized I’d been there long enough and had nothing left to learn … I walked in and quit that day on the spot. I had no...
A Look Back: Hypergrowth, No Office and $100M in ARR with Seth Shaw, ex-CRO Airtable and CCO at Invision
Seth Shaw was most recently CRO at Airtable, and before that, CCO at Invision and VPS at Wrike. He was one of the early sales leaders managing a distributed sales team, and it’s interesting to look back at his 2019 talk at SaaStr on just how hard it can be...
Nick Mehta, CEO Gainsight: My Top 10 Failures as a SaaS CEO & What I’ve Learned (Video + Podcast)
In this session Nick Mehta will share ten significant mistakes he made during his career, and how these failures shaped his journey as CEO of Gainsight. Mehta will impart valuable lessons on resilience and growth, offering attendees actionable takeaways for their own entrepreneurial ventures. This talk is a must-watch for anyone seeking to learn from real-life experiences and turn failures into opportunities for success in the software-as-a-service (SaaS) world.
Dear SaaStr: Is 5 Co-Founders Too Many When Raising Venture Capital?
Dear SaaStr: Is 5 Co-founders Too Many When Raising Venture Capital? Yes, it can work. My first venture investment was Pipedrive, it had 5 co-founders and sold for $1.5 Billion. 10 Years of Investing pic.twitter.com/zsSupe0CRP — Jason ✨Be Kind✨ Lemkin ...
Dear SaaStr: Why Do VCs Want to See At Least 2 Co-Founders?
Dear SaaStr: Why Do VCs Want to See At Least 2 Co-Founders? First off, note that clearly it is possibly to build a huge SaaS company without a traditional co-founder. It’s not the most common path, but now we can see that a number of leaders have done it: Zoom,...
SaaS CEOs That Go The Distance, To IPO … Tend To Be Founder-CEOs (Updated)
Non-founder CEOs get fired all the time — and these days, are quitting more often than ever. Founder-CEOs getting fired seems rarer these days, though. OpenAIs, Ubers and WeWorks aside. Two that would be hard to imagine happening today: Pushing Steve Jobs out...
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...
Is Your VP Too Hard to Work With? The 2 Hour Rule
If you’re reluctant to ask someone to do part of their job If it’s just easier to do it yourself If you don’t want to argue when you ask 100% clear sign it’s time for someone new in that role — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) May 4, 2025 So we’ve talked a...
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: 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...
Lessons on Scaling Customer Success from $1M to $300M in ARR with Success Venture Partners
Learn what it takes to scale Customer Success at every stage of growth — from $1M to $300M+ in ARR — with founder and Managing Partner at Success Venture Partners and former VP of Customer Success at Motive.
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