A Look Back: Olivier Pomel, CEO of Datadog at $100,000,000 in ARR
As we gear up for SaaStr Annual 2025 in the SF Bay Area on May 13-15, we wanted to take a look back at some of our most iconic speakers and sessions from over the year, that we can still learn from today. Today, Datadog is at $2.5B+ ARR. It’s a suite that most...
You Won’t Know Most of Your 10x Hires Are That Good on Day 1
So Auren Hoffman did a SaaStr workshop a few years back that was one of my favorites, I’ve embedded it below. He made many great leadership points, but one in particular rattles around my head a lot and I think deserves its own post: You usually won’t know if you’ve...
Dear SaaStr: What Happens After You Raise Venture Capital for the First Time?
Dear SaaStr: What Happens and Changes After You Raise Venture Capital for the First Time? A few thoughts if you haven’t raised venture capital before: 1. Remember you have to prove yourself, still. Yes, you got the $$$, and they really can’t get it back, and...
Gartner: 2024 Will be Tougher Than We Thought, But We’ll Still Cross $1 Trillion in Software Spend
So Gartner is cutting back its growth projections for 2024 a bit. It was previously projecting a 13.8% spend in software spend in 2024 to over $1 Trillion. It’s now cutting that back a bit to 12.7% growth in 2024, basically flat with 2023. But that’s...
Dear SaaStr: What Are The Most “Evil” Things That VCs Do?
Dear SaaStr: What Are The Most “Evil” Things That VCs Do? I’ve been on every side of the table, and had challenging experiences with my investors. I think what founders get wrong is not understanding incentives. VCs really do want you to be a big success....
5 Interesting Learnings from SmartSheet at $1 Billion in ARR
So there’s a quiet leader in the work management space that’s quietly … blowing the doors off. Everyone knows Atlassian, Asana, Notion, probably Monday. But Smartsheet? You should know them. They’re at $1 Billion in ARR now, growing an...
How Enterprise Companies are Buying AI (or Not) with ContextualAI, Anthropic, Glean, and Unusual Ventures
While AI seems to have gone mainstream for consumers and smaller SaaS companies, but what about the big guys? While the first generation of Generative AI is great, it’s not quite ready to solve Enterprise problems. So, where are we now in the adoption cycle for the Enterprise world?
We brought together an Enterprise SaaS panel with:
Douwe Kiela, CEO of ContextualAI
Benjamin Mann, co-founder of Anthropic
Arvind Jain, CEO of Glean
and Sandhya Hedge, General Partner at Unusual VC,
To help us figure out how to sell GenAI software to some of the biggest organizations in the world.
Venture Backed or Bootstrapped? There’s a Third Way. Just Raise One Round.
"You don't have to raise $10m, $20m, $100m in venture capital. You can raise just one round if you want. A one-and-done. And maintain so much more optionality." w/ @thesamparr pic.twitter.com/6IGJrVB5GT — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin...
66% of You Feel More Burnt Out Than Ever. A Few Things That Don’t Actually Seem to Help.
So I have a ton of empathy overall for the journey in SaaS. It’s a long, 7-10 year journey to really build anything big, minimum. But empathy for burnout? Sort of. I do have empathy for founders, execs and ICs that truly left nothing on the field for 3, 4, 5...
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