Dear SaaStr: How Much Do Founder-CEOs Own at Time of Exit?
Dear SaaStr: How Much Do Founder-CEOs Own at Time of Exit? It can vary a lot, of course. If you never raise venture capital, the founder-CEO might own 50%, or even 100% in some cases. The founders of $10B+ Mailchimp still own 100% of the company, for example. But, on...
The CEO of An AI Agents Company We Really Love Asked Why We Didn’t Pick Them. Here’s the Honest Answer.
The CEO of an AI Agents company we genuinely admire reached out recently and asked why we didn’t select them as a vendor. It was a fair question — they have a great product. The honest answer? Their VP of Sales argued with us. Wouldn’t do any work up...
Brex and The Pros and Cons of Hubristic Fundraising
Capital One just announced it’s acquiring Brex for $5.15 billion. An incredible, top 0.1% “exit” in less than 10 years from a category creator that created massive wealth and opportunities. A huge win. But also … less than half of Brex’s $12.3 billion...
AI App of the Week: Vivun — The AI Sales Engineer That Actually Does the Work
The Bottom Line: Ava by Vivun is an AI sales teammate built by founders with 25+ years in technical sales. It’s not a call summarizer—it preps you before meetings, answers complex questions in real-time during calls, and generates the follow-up materials after....
Dear SaaStr: What’s The Typical Enterprise SaaS Cancellation Policy For $100k ACV/Bigger Deals? Should The Contract Have a Fine?
Dear SaaStr: What’s The Typical Enterprise SaaS Cancellation Policy For $100k ACV/Bigger Deals? Should The Contract Have a Fine? Generally, just track to the cash. Anything more than that isn’t worth the energy and effort: If a customer has signed a pre-paid...
If AI GTM Tools Were Half as Good As Cursor or Replit, It Would Be a Different World Today. They Will Get There.
We’ve been running AI GTM agents for almost a year now. We use Artisan for outbound, Qualified (now Salesforce) for inbound, Agentforce for Salesforce-native outreach, Delphi for Digital Jason. We’ve sent 20,000+ AI messages and generated over $2M in...
a16z’s State of Markets: $5.5T in Private Unicorns, <5 Public Companies Growing 30%, and 8 Other Data Points You Need to See
a16z released their inaugural “State of Markets” deck this week. Here are the 10 top takeaways for B2B founders and execs: #1. $5.5 Trillion in Private Unicorns — 10x Growth in 10 Years Private tech companies valued above $1B now represent ~$5.5T in...
20VC x SaaStr Are Back: If Figma Isn’t Good Enough, What Hope Is There? Plus OpenAI Ads, Elon vs. Sam, and the $9B Replit Bet
With Harry Stebbings, Jason Lemkin, and Rory O’Driscoll If Figma—one of the best products in SaaS history—can’t sustain its IPO price, what does that mean for the rest of us? That’s the question that kicked off this week’s episode, and it led...
We Built Our Own AI VP of Marketing. Here’s What It Actually Does.
We didn’t want to build it. Let’s be clear about that upfront. We wanted to buy an AI agentic solution that does what we need in marketing. We looked. We demoed. We really, really tried. But we just couldn’t find one that does what we actually need....
Wing Ventures’ State of the AI in the Enterprise: 50% of Pilots Succeed, 53% See Positive ROI, and 70% See AI Replacing Even More Humans
Wing Ventures interviewed 180+ C-level execs on AI for its new State of the AI in the Enterprise report here. The learnings weren’t radical, but they did quantify a number of interesting observations in AI: #1. 50% of AI Pilots Proceed Into Production A great...
By Late 2025, Replit Got Really Good. Now Imagine If Your Agents Really Could Run 24×7.
When we started on Replit in mid-2025, the idea you could build a commercial-grade B2B app on it was … a fiction. With very short context windows and limited capabilities, thinking you could vibe code a “Salesforce” was borderline ridiculous. Maybe it still is, But …...
Should You Pay Reps More For Deals They Hunt Themselves? Sometimes. Here’s When.
Dear SaaStr: Should sales reps be compensated differently based on how much prospecting they do? For example, if all of their leads come inbound (without effort on their part) should they receive a lesser % per deal vs a rep that prospects for their own leads? It...
Strange World Indeed, January 2026 Edition: The Massive, Unprecedented Divergence Between Public B2B and Private AI B2B
We’re living through something we’ve never quite seen before in B2B software and SaaS. It’s arguably the worst time in our history to be invested in public software stocks. Multiples at all time lows, and crashing hard in 2026. And simultaneously,...
Dear SaaStr: How Do I Pay My Sales Reps on Monthly Deals?
Dear SaaStr: What is the better SaaS sales compensation plan: paying reps the 12 months up front for the contract value or paying them pro-rated 12 monthly payments? You may be tempted to pay reps monthly for monthly deals. While that’s not uncommon (see the...
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