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...
Dear SaaStr: Should I Fire a Sales Rep That Lied To Several Customers?
Dear SaaStr: Should I Fire a Sales Rep That Lied To Several Customers? Earlier in my career, I would have said Yes. Of Course. Fire any sales rep that lies to customers. Especially more than once. Especially in my first start-up, we worked in a heavily regulated,...
Your #1 Job For January? Deploy An AI Agent — Yourself. Hands On Keyboard
We just did a deep dive with Lenny Rachitsky on what we’ve learned deploying 20 AI agents at SaaStr. And I want to share what I think is the single most important piece of advice for any sales, marketing, or GTM leader heading into 2025: Pick one AI agent....
Your Job In AI + B2B in 2026: Grab The Tailwinds, For Real. It’s Not Too Late. But It’s Different. (Updated with Video)
The B2B market in 2025/2026 is experiencing a paradox that every founder, CEO, and investor needs to understand: there’s more capital, more budget, and more opportunity than ever before. But the thing is .. that incremental B2B budget it’s not evenly...
Dear SaaStr: As a Co-Founder, How Do I Tell the Team I’m Leaving?
Dear SaaStr: As a startup founder, what’s the best way to announce your departure to the team and leave on good terms? The startup is series A/B, with 30+ employees. I have no magic insights, but I have transitioned post-acquisition out of 2 companies that...
Right Now, Managing AI Agents is About as Much Work as Managing Humans. Just Different Work.
Here’s something almost nobody tells you when you deploy your first AI agent: you’re not eliminating management overhead. You’re trading one type of work for another. It’s different work. But it requires about as much time for oversight,...
SVB’s State of the Markets Report: AI Isn’t More Efficient, VC Dollars Are Even More Concentrated, and M&A is Picking Up But Fewer Deals Make Money
The latest SVB State of the Markets report just came out, summarizing all their venture and startup activity through 12/31/25 or so. This is their 30th edition, and buried in these 34 pages are some hard truths that every founder, operator, and investor in B2B needs...
CROs at Slow-Growth Companies Often Aren’t Really CROs. They’re Chief Price Raising Officers.
Here’s a pattern I’ve seen play out dozens of times now, and it’s worth talking about honestly. When a B2B company’s growth slows — say, drops from 50% to 20% or even 15% — the CRO role fundamentally changes. Not officially, of course. The...
Hooray, You Got Profitable. That’s Great, But It’s Not Enough. It’s Time To Reaccelerate Growth.
You did the easiest hard thing. You cut the burn the last 6, 12, 24 months. You right-sized the team. You got to profitability—or at least cash-flow positive. You survived when so many others didn’t. And that matters. A lot. But here’s the uncomfortable...
How Much Equity to Give Your First Employees: The Real Data from 50,000 Startups
One of the most common questions I get from seed-stage founders: “How much equity should I give my first hires?” It’s a high-stakes decision. Give too little and you can’t attract talent. Give too much and you’ll regret it by Series B...
Jason + Lenny are Back!! “The Real Future of AI in Sales”
So in early 2024, Lenny Rachitsky invited us on to Lenny’s podcast for what became an iconic deep dive on sales and GTM. How and who to hire, the classic GTM and sales mistakes we all make, and more. It was great. It was also … an entire era ago. The end of the...
We’re Literally Just Getting Started in AI + B2B. Here’s Why 2026 Is When It Gets Real.
I know, I know. You’ve been hearing about “AI transforming B2B” for two years now. Your LinkedIn feed is drowning in it. Every vendor has slapped “AI-powered” on their homepage. But here’s the thing: we’re actually just now...
The Navan IPO Reminds Us: AI is On Fire. Everything Else in B2B? Still Really, Really Hard.
So Navan finally went public in Q4’25. After years of confidential filings, pushed timelines, and a rebrand from TripActions, they rang the bell on October 30th, 2025. And then the stock dropped 20% on Day One. Today? It’s trading around $17. That’s 32%...
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