How to Make Sure Your AI SDR is Actually Any Good? You Have to First Copy Your Best Human
Most folks deploying AI SDRs and similar tools are doing it all wrong. They think the tool can magically on its own figure out how to sell for you. It can’t. At least not today. None of them can. Here’s what nobody tells you when you’re shopping...
When the Most Expensive LLM Isn’t Worth It: What We Learned Analyzing 3,000+ VC Pitch Decks and 850,000+ Startup Valuations
There’s a temptation in AI to always reach for the biggest, most powerful model. The latest release. The premium tier. The one with the best benchmarks. Especially given the incredible pace of competition and innovation in AI + B2B today. And sometimes...
Dear SaaStr: We Lost an Enormous RFP Because We are Too Small. Any Advice?
Dear SaaStr: We lost an enormous RFP because we are too small. Any advice? This is indeed a big bummer. But it truly does make you stronger — if you commit to winning the next one. Six thoughts on how to do better next time: First, move them into your Lost Now...
If You’re Going to Stick with a Mediocre VP for Now, You At Least Have to Micromanage Them
I know this is advice you probably don’t want to hear. We’ve all been told that micromanagement is bad. That great leaders hire great people and get out of their way. That autonomy is the secret to building high-performing teams. And that’s 100% true. For...
Yes, M&A is Back. But Confirmed 3x+ Returns Have Collapsed to Just 7% of Deals. Here’s What That Means for Your Exit.
There’s been some epic M&A in the past 12 months. Nvidia paid $20 billion for Groq. Google closed its $32 billion acquisition of Wiz. Google paid $2.4 billion just to hire Windsurf’s CEO and license their tech. Palo Alto Networks is buying CyberArk for...
How Long It Really Takes to “One-Shot” an App: 47,000 Lines of Code Later
The vibe coding hype cycle has a narrative problem. Every week, someone posts “I built a SaaS in 4 hours!” And technically, they’re not lying. You can absolutely scaffold something that looks like a product in an afternoon. But there’s a...
The Change You Need Is the Change You Make. SaaStr AI Annual 2026 Will Help You Get There.
Here’s what I’ve learned after 13 years of building SaaStr, investing in 50+ leading B2B companies, and watching thousands of founders navigate moments of massive disruption: The founders who win aren’t the ones who figure it out alone. They’re...
Dear SaaStr: How Do I Deal With Investors That are Unhappy With The Company?
Dear SaaStr: How Do I Deal With Investors That are Unhappy With The Company? Be transparent. And show them an honest, data-driven path to a better future. First, investors get most upset when founders hide things. And founders tend to hide things more when times are...
20VC x SaaStr Is Back!!: Nvidia’s $20B Groq Grab, Meta’s $2.5B Manus Play, and Why “Invisible Unemployment” Will Define 2026
The latest from the 20VC x SaaStr collaboration with Harry Stebbings, Jason Lemkin, and Rory O’Driscoll Jensen Huang wanted the deal done before Christmas. He got it in two weeks. Nvidia just dropped $20 billion on Groq—a company doing sub-$50 million in...
OneStream Goes Private, Navan at 4x ARR: Are The IPO Markets Really That Open?
So this week, OneStream announced it’s going private. Just 17 months after its IPO. Let that sink in. KKR took OneStream public in July 2024 at a $6 billion valuation. The stock opened 29% above its $20 listing price. Everyone celebrated. The IPO window was...
How Personio’s CRO Built an AI-Powered Go-To-Market in Just 6 Months: 5 Lessons and 5 Mistakes
Philip Lacor is the CRO of Personio, a $3B+ HR and payroll platform with 1,500 employees, 15,000 customers, and a 400-person sales team. He shared their AI transformation journey at SaaStr AI London — and the learnings are a masterclass for any revenue leader trying...
Dear SaaStr: How Can a SaaS CEO Tell Which Customers are 10+ Year Customers?
Dear SaaStr: How Can a SaaS CEO Tell Which Customers are 10+ Year Customers? I think it’s fairly easy. Look for: Are they running an entire division or group (or more) on your product? Is the use case mission critical — even if niche? I.e., would the business be at...
The Rise of Invisible Unemployment in Tech: 2026 Will Be The Year When Everything Really Changes
Invisible Unemployment is going to really pick up in tech in 2026.  It’s already here. It just doesn’t show up in the numbers yet. And yes, it’s fueled by AI—but not in the way most people think. The unemployment rate in tech looks fine on paper....
5 Interesting Learnings From Motive at $500,000,000 ARR. And The Match Up With Samsara.
Motive filed its S-1 to IPO, and now we can finally see the real numbers behind one of the fastest-growing fleet management companies ever built. And with somewhat direct competitor Samsara trading at a ~$20B market cap and just hitting GAAP profitability for the...
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