I Was Wrong About Marketing ROI. Here’s What $100,000,000+ in Sponsorship Sales Taught Me.
We’ve closed over $120,000,000+ in sponsorships at SaaStr over the years. And I’m still learning about real marketing ROI from them. For a long time, I thought most marketers were doing it backwards. Here’s the pattern I kept seeing: when a...
2026 Is The Biggest IPO Year In History. But Take Out SpaceX And Right Now It’s One of the Worst.
A good year for IPOs. A bit less so for their performance. And not a year at all for SaaS. Per PitchBook there has been $1,786.8 billion in US VC-backed IPO value through July 28. That’s not a record. That’s five prior years stacked on top of each other...
The AI Board Member: Should Yours Should “Chair” the Next Meeting? At Least Conceptually
I just got out of a 3 hour board meeting where the first 2 hours were an almost total waste of time. 5 busy executives reviewed 30 slides that no one really had read ahead of time. And then a bunch of VCs made generic comments that sounded directionally correct but...
Jason’s Takes on This Week’s 20VC: The Toggle Is a Permission Grant, The Blame Test Decides the Deal, and Why Five Years of Price Increases Is a Countdown
The version of this week’s episode I’d give a founder over coffee, including the part where an agent rewrote my core algorithm and I found out from a merge conflict. Harry, Rory and I covered Jensen’s open-weights letter, the OpenAI model that...
The #1 Most Important Thing to Understand About AI SDRs: They Can’t Figure It Out For You. That’s Still Your Job. For Now, At Least.
10x Times Zero Is Still Zero: The #1 Thing to Understand About AI SDRs AI SDR and AI GTM agents are everywhere now. Every vendor promises they’ll 10x your pipeline. And they do work. They really do. We have the data 😉 From Agentforce to Artisan to Qualified to...
Dear SaaStr: I Fired My VP of Sales. What Now?
Dear SaaStr: I Fired My VP of Sales. What Now? It’s tough and there may be some bumps. But honestly things probably will be better in just a week or two. What you do need to do is have a plan. You need to act fast and smart to stabilize and rebuild. Here’s what...
5 Interesting Learnings from Procore at $1.5 Billion in ARR: 16% Growth, Its First GAAP Operating Profit, and $845M for DroneDeploy
Procore’s one of the great pre-AI vertical software leaders. Construction software, 3 million projects, 150+ countries, roughly $1.5B in ARR. But growth slowed as for many the past 24 months. They’ve finally turned it around a bit. And then spent $845...
When a 3.8x “Exit” Becomes 1.6x: The Gap Between Markups and Returns
One of our older SaaStr Fund companies was recently acquired. It is selling for 3.8x what we paid to get in years ago. On paper that reads like a clean triple. We won’t make 1.6x. That gap, 3.8x on the marquee valuation versus under 1.6x in the bank, is one of...
20VC x SaaStr: Jensen’s First Tweet Ever, The Agent That Rewrote My Code Without Telling Me, and Why The PE Turnaround Playbook Is Out Of Road
This week on 20VC with Harry Stebbings and Rory O’Driscoll: the open-weights letter that Anthropic didn’t sign, the OpenAI agent that broke out of its sandbox and went hunting for test answers on Hugging Face, Etched raising $300M, Alphabet posting its...![The One Hire You [Probably] Just Can’t Make: Chief Product & Technology Officer](https://i0.wp.com/www.saastr.com/wp-content/uploads/2026/02/Young-CPTO-Sleeping-scaled.jpg?resize=1000%2C565&quality=70&ssl=1)
The One Hire You [Probably] Just Can’t Make: Chief Product & Technology Officer
I see them everywhere now. Chief Product & Technology Officers. CPTOs. Whatever you want to call them. They’re popping up at B2B companies north of $100M ARR. Especially ones in transition, trying to get more agentic and “more AI.” Look tiles are...
Dear SaaStr: How Do You Steal Customers From the Leader in the Space?
Dear SaaStr: How Do You Steal Customers From the Leader in the Space? There are so many products I would buy if the vendor just said "I'll do all the work for you" Instead, they all just want to tell me why they are 10x better But not really help me:...
AI Isn’t Killing SaaS. SaaS Is Killing Itself.
Everyone wants the story to be about AI. AI is replacing seats. AI is collapsing pricing. AI is eating the workflow. There’s truth in all of it, and we write about it here every week. But in many ways the bigger story is the one nobody really discusses, because...
It’s Time for a New VP. Can You Pull Off a Stealth Search?
So many founders go through a process where they finally realize a VP isn’t working out, but they still want to keep them while they find their replacement. They want to do a Stealth Search. All I can tell you is: This is really, really hard, and rarely done right As...
Dear SaaStr: What’s the Best Advice Founders Never Hear?
Dear SaaStr: What’s the Best Advice That Entrepreneurs Never Hear? My list of top advice founders never hear: Slow it down if you don’t have a great co-founder. We all get excited to “get going” with a start-up. But if your co-founder isn’t great, if they don’t...
Founder SaaStr
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