Anthropic filed its amended S-1 this week, with audited Q3 numbers that replace what leaked from October’s investor day. Revenue rose to $16.96 billion from $11.56 billion in the second quarter. That is up 1,127% from $1.38 billion a year earlier and 47% from the second quarter. The cost side, the customer base, and the…
Continue Reading

In B2B, #1 most common mishire, with a bullet, is the CRO/VP/head of sales. In fact, there’s a VC saying that I used to really hate. It goes something like “You’ve Got to Get Past the Carcass of Your First VP of Sales” or “It’s The Second VP of Sales When You Really Start Selling”…
Continue Reading

Dear SaaStr: Should You Hire Someone That Seems Good … But Always Job Hops? I know there are a lot of views on this question, and job hopping has certainly accelerated in the Age of AI. But I’ve reflected on many years of hiring here, and for me at least, here’s what I’ve learned: #1….
Continue Reading

Last week a sales rep at one of the leading public B2B software companies emailed me twice in 48 hours. The first email offered “insights” on buyer intent and AI efficiency … and shared none. It just listed their three product lines, and asked if I wanted to “benchmark” their software. The second email, sent…
Continue Reading

So when growth slows, the conversations change. Especially from your CRO. When growth slows, the conversations change. Especially from your CRO. You start to hear: A ton of talk about raising prices. A lot. There are good reasons to raise prices. You added a lot of value, the market moved, you were underpriced from day…
Continue Reading

Dear SaaStr: Do VCs Want To Talk To Senior Execs That Quit a Portfolio Company? Sort of. Maybe. Generally, if the issues are around: harassment or any inappropriate conduct, or fraud or misleading financials, etc, or something else that is wrong legally, ethically, morally, financially, etc. then I definitely need and want to have the…
Continue Reading

What founders should do differently after Anthropic’s S-1, Microsoft’s buyout offer, Cloudflare’s 20% cut, and a Qwen model trying to reach a server in Beijing Every Thursday, Harry, Rory and I go through the week’s news on 20VC x SaaStr. Here are the 10 things from this week’s episode I’d want a founder to act…
Continue Reading

The other day one of the core products we run SaaStr AI on went down the entire day. Not degraded. Down. For the entire day. Every screen in the app showed a large “INTERNAL ERROR.” The API returned the same thing, which meant every agent workflow that touched this product stopped cold. And we run…
Continue Reading

"A VP Sales, Product, Customer Success, all of them … have to meet customers their first week. They have to. Or don't hire them. You'll be surprised how many folks want to be managers, but not meet customers or do a lot of the work themselves. So ask them. Ask them what… pic.twitter.com/QyicrUVmks — Jason…
Continue Reading

Dear SaaStr: How Do I Find Product Market Fit In the Early Days? Find a little bit of it first ;). Just a little bit. And then relentless build on top of that. Finding product-market fit is the single most important milestone for any startup. Without it, nothing else really matters. Product-market fit, definition: When…
Continue Reading

Two things happened within 24 hours this week. Together they say more about where B2B is going than most of the “SaaS is dead” takes from the past 18 months. On Thursday, shares of ServiceNow fell 26.9%, while the S&P 500 slipped 0.3%, after its October 28 Q3 report. On Friday morning, Bret Taylor and…
Continue Reading

I'd say about 66% of founders step back from sales when they hire a VP of Sales 95% of the time, it backfires You don't get that time back. You just use it in different parts of the sales process. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) May 27, 2026 So much of classic SaaStr content is…
Continue Reading

Dear SaaStr: How do you structure a sales team … when you’ve got zero experience doing sales? Well, first go get some experience with sales. 🙂 At least, close the first 10 customers yourself. If you don’t, you’ll never have any idea how to do it. And the odds your first rep succeeds goes way,…
Continue Reading

Salesforce agreed the other day to buy Braze for $5.66 billion, 6.8x trailing revenue. In most of B2B that price would be unremarkable. In go-to-market software it’s a 58% premium, because Braze traded at 3.7x on Monday. I pulled the multiples for the public GTM and front-office apps and compared them with infrastructure and security….
Continue Reading

Annual contracts seem so great. VCs love them, and they do seem to reduce churn. Seem to. In fact, when CROs struggle to hit a plan, they often want to push customers onto annual contracts. That and pricing increases are classic go-to moves. I’ve long been a vocal proponent of annual contracts. I felt like…
Continue Reading