Dear SaaStr: What’s It Really Like to Be CEO of a Startup? Let me just throw out a few things I’ve learned that being a CEO of start-up isn’t, or isn’t as you’d expect: It isn’t glamorous until you are At Scale and Hot, at the very minimum. At...
I get it. A lot of jobs in tech just aren’t that rewarding anymore. If they ever were. At least in 2021, they were kind of easy, and you got to work from home, often < 30 hours a week. These six figure jobs honestly aren’t all that great, in many...
Anthropic just published a breakdown this week of where AI agents are actually deployed across nearly 1 million real production tool calls. Software engineering sits at 49.7%. Sales and CRM is at 4.3%. Finance at 4.0%. Legal at 0.9%. At first it might seem to say AI...
Dear SaaStr: What Are The Top 5 Things I Should Know Before Starting a SaaS Startup? My Top 5: It will take you at least 24 months to really get anywhere. Everyone mentally budgets 10–12 months. It’s never enough. At least, not to get enough paying customers from Code...
Dear SaaStr: What is The Biggest Pain for a CEO? Competition is stressful. Raising funding can be hard. Partnerships can be frustrating. But the hardest part is always recruiting. And it never gets easier, not really. Every CEO I see past $2m in ARR or so, be it...
There’s been a massive SaaS sell-off since mid-2025. Multiples compressed. Growth stocks punished. The “SaaS is dead” takes are everywhere again. B2B isn’t dead. Software is still eating the world. Businesses still need tools. Enterprise...
Canva just reported $4 billion in ARR per TechCrunch. And per COO Cliff Obrecht, it’s growing a stunning 35% $23M in 2018. $4,000M in 2025. 173x in seven years. It’s one of the most extraordinary B2B growth stories ever built — and it barely gets the...
Dear Saastr: As a CEO, How Do You Know That Your New Employee is an A,B, or C Player? You might not at first. So get help. But you’ll get better at this. As a first-time manager, you really won’t have the experience to know really who is an A, B or C player for any...
For most of the past decade-plus, B2B software had a beautiful, almost boring stability to it. You’d build a product. You’d get it to $1M ARR. Then $10M. Then $100M. And the product you were selling at $100M ARR looked … pretty much the same as what you...
SaaStr AI 2026 is running 132% of where we were at this point last year. Tickets are up. Sponsors are up. See everyone in San Francisco, May 12-14. We’ve got the best of the best coming — Databricks, Replit, Agentforce, Lovable, Google Cloud, and so much more....
