Dear SaaStr: How do I prepare myself to become a successful startup CEO? My list of 6 things that will help: #1. Manage People This is one of the best things you can do, because 50% of the job of a CEO is recruiting a team, leading a team, empowering a team,...
We did a deep dive on 20VC x SaaStr this week with Mike Cannon-Brookes, co-founder and CEO of Atlassian. Atlassian just put up an incredible quarter of accelerating growth (23% at $6.4B ARR, with RPO growing to 44%). And yet the markets aren’t showing anyone...
Not every role goes away. Not every AI works without humans. But if you’re still running a 2021 sales org, you’re already behind. I’ve been getting a ton of questions about what the sales team actually looks like in 2026. And I’ve been living...
Dear SaaStr: What Are The Biggest Lessons You’ve Learned from Failure as an Entrepreneur? Don’t Fail. I’ve almost failed several times. Really almost every time. But never actually failed. Why not? Never quit. You can’t fail if you don’t quit. Find...
I’ve been tracking CS Disco (NYSE: LAW) since I was the first investor in a legaltech eDiscovery competitor to it, Logikcull, way back in 2015. They IPO’d and then in 2021, and we wrote about them when they hit $120M in ARR. Back then, the stock was...
New data from Pave across 386,500 new hires tells a striking story: the percentage of new hires going into Customer Support has dropped from 8.30% in Q4 ’23 to just 2.88% in Q3 ’25. That’s a 65% decline in two years. And the curve is accelerating —...
Dear SaaStr: When Is It Too Soon to Target Enterprise Customers in SaaS? It too soon to target enterprise clients when you can’t support their needs 90 days after you close them. It’s sort of OK in the enterprise to promise features and functionality that are sort of...
Atlassian just reported its Q2 FY26 results, and they’re fascinating on multiple levels: $6.4B+ ARR, $1.6 billion in quarterly revenue, up 23%. Atlassian is accelerating (albeit modestly) — up from 20% growth Their first-ever $1 billion cloud quarter. And...
Dear SaaStr: How Can You Land Big Customers If You’re a New Startup No One Has Heard Of? Solve one of their top pain points, for real — that no other vendor is solving. And do it in a way that isn’t super risky. If you haven’t sold to the F500 / Global 2000...
Anton Osika, the CEO of Lovable, just shared something really interesting — their top 4 actual use cases for vibe coding in businesses right now. Lovable is now the second-fastest growing software product among businesses on Ramp. These are the main use cases for...
