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...
Your Agents Are About to Start Firing Your Vendors. Ours Fired Marketo.
We just moved 10+ years of data off Marketo into Salesforce Marketing Cloud. It took us years to get there. The final straw was the rate-limiting in their API made it unusable for 10K, our AI agent for marketing and revenue. The renewal came up, they raised prices...
Dear SaaStr: How Should I Specialize My Sales Team?
Dear SaaStr: How Should I Specialize My Sales Team? If you’re asking the question, then the answer is probably yes 😉 One thing is clear: most founders and VPs of Sales and CROs look back and wish they’d specialized their sales team earlier. And not have...
The Top 12 Sales Lessons From SaaStr AI 2026: Anthropic, Gamma, Owner, Stripe, Salesforce, Vercel, Replit and Monaco
The sales and GTM sessions at SaaStr AI 2026 in San Mateo was all about where to take agents next. No one was still debating whether to put agents in the revenue org. They had already done it, and they brought the war stories. What broke, and what they would do...
Dear SaaStr: We Have a Sales-Led Motion and SMB Customers And The Economics Aren’t Working
Dear SaaStr: We Have a Sales-Led Motion and SMB Customers And The Economics Aren’t Working. What Do You Suggest? You have to be ruthlessly efficient with a sales-led SMB motion. It can be done: Toast does it at a $10k ACV with fairly low gross margins: Slice...
Our New AI VP of Finance Closes the Deal, Sends the Invoice, and Chases the Cash. It Took 4 Deals to Train It.
Our finance team went on vacation during SaaStr AI Annual. Our busiest time of the year. That’s the whole origin story. Collections started slipping, sponsors and vendors weren’t getting billed, and the work that has to happen after a deal closes stopped...
Founder SaaStr
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