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...
What To Do When A Customer Wants to Cancel A Contract
Hopefully, 100% of your customers love you. But as time goes on, you’ll oversell a few deals. Or not quite deliver in some fashion. Or fail to deploy in others. And some customers will ask for their money back. When they e-signed binding, good old-fashioned...
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...
Dear SaaStr: What Were Aspects of Your Startup That Were Easier Than Anticipated?
Dear SaaStr: What Were Aspects of Your Startup That Were Easier Than Anticipated? The part I didn’t originally get as a first-time B2B founder was how relatively easy it is to grow exising accounts and account size if your customers are happy. 120% NRR: Your revenue...
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...
Dear SaaStr: What Do You Do With Churned Customers?
Dear SaaStr: What Do You Do With Churned Customers? You put them into a Get Them Back bucket and re-market to them with a dedicated program. And you have sales especially follow-up twice. Once in about 90 days, to see if they might want to come back —...
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...
Dear SaaStr: Should We Drop Customers That Complain Too Much?
Dear SaaStr: Should We Drop Customers That Complain Too Much? Sometimes, yes. But just as often, the ones that complain are the ones that care. And oftentimes, their complaints help focus you on the gaps you really do need to fix. One thing most SaaS companies get...
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...
Dear SaaStr: What’s The Best Way to Get Traction After We Have Our First Few Paying Customers?
Dear SaaStr: What’s The Best Way to Get Traction After We Have A Few Paying Customers? Answer: try everything that just might work, even a little bit. Then: double down on anything that works even a little. That may sound obvious, but what I mean is, most start-ups...
Founder SaaStr
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