With Harry Stebbings, Jason Lemkin, Rory O’Driscoll, and special guest Mike Cannon-Brookes (CEO and co-founder Atlassian) We’re back on 20VC, with Harry, Rory from Scale, SaaStr’s Jason Lemkin, and a very special guest — Mike Cannon-Brookes, CEOand co-founder of Atlassian. On Anthropic’s $149B revenue projection and whether CIO budgets can actually support it, why “software…
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And Raised $30 Billion at a $380 Billion Valuation To Boot. So this week Anthropic officially closed its $30 billion Series G — the second-largest private tech round ever, behind only OpenAI’s $40 billion raise — at a $380 billion post-money valuation. That’s up from $183 billion just five months ago in the Series F….
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Dear SaaStr: If We Have Two Overlapping Products is it Better to Have One Sales Team or Two? It’s almost always better to have different sales teams handling different products Why? If for no other reason — Incentive Alignment. Sales reps work on commission, and they are driven almost entirely by what they get the…
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There used to be a lot of companies in the 10x ARR Club. In Q4 2020, 60% of public B2B companies traded at 10x revenue or higher. Thirty-five traded above 20x. Asana hit 89x. Today it’s at 3x ARR.The median SaaS multiple was north of 18x. That world is not just gone. It’s been obliterated….
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We just had a great session at the last SaaStr AI Annual from Firebolt on something I think every B2B SaaS founder needs to internalize right now. The punchline: we’re entering a third go-to-market era — and most of you aren’t ready for it.   The Data Is Brutal Right Now Let’s start with reality….
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The Bottom Line: People.ai has been building the AI data layer for revenue teams since 2016 — years before “AI-native” became a buzzword. Founded by Oleg Rogynskyy (who came to the U.S. from Ukraine at 15 and started at Boston University), the company has trained its models on billions of sales interactions across emails, meetings,…
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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, convincing a team….
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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 much love. Mike was honest and reflective on just what’s…
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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 it—we went from 10+ humans in sales at SaaStr to 1.2…
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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 great co-founders. If you find truly great cofounders, you always have another card to…
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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 trading at almost 20x ARR. The market cap…
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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 — almost half the drop happened in the last…
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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 there … so long as you deliver…
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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 yet the market “hates it”. The stock is sitting near its 52-week low at ~$98, down…
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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 before,…
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