SaaStrAI
B2B + AI Community, Events, Leads
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Latest posts
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Jason’s Takes on This Week’s 20VC: Anthropic’s S-1, Microsoft’s 27% Buyout, and My 100-Day Rule
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…
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Our Core Vendor Was Down for 24 Hours. Our AI Agent Replaced Them Before They Came Back Up.
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…
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SaaS Isn’t Dead. Old SaaS Is Dead: Sierra Adds $150M ARR in One Quarter While ServiceNow Drops 27% in a Day
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…
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The B2B Category the Markets “Hate” the Most Today: GTM
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…
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Annual Contracts: Maybe Not All They Are Cracked Up To Be
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…
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20VC x SaaStr: Anthropic’s S-1 Shows $16.3B in First-Half Revenue, Microsoft Offers Buyouts to 27% of Its Staff, and Chinese Open-Weight Models May Be Done in the US
Plus Broadcom backstopping Anthropic’s chip debt, Meta’s $95B equity raise, the PHP2Shell flaws, and an IC fight over Instinct at $30B and OpenAI at $1.25T This week had one story that mattered more than everything else combined: Anthropic finally filed its S-1. Harry Stebbings,…
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5 Interesting Learnings from Guidewire at $1.24 Billion in ARR: A $1.7 Billion AI Acquisition, Its Lowest Churn Ever, and 10x ARR for a 25-Year-Old System of Record
Guidewire sells core systems to property and casualty insurers: policy, billing, and claims. It was founded in 2001. Its buyers are some of the slowest-moving in B2B. In a year when the market repriced anything that looked like legacy software, it still trades at roughly 10x…
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Sponsor SaaStr AI Annual 2027. Walk Out With 85+ Customer Meetings Set.
A few months after SaaStr AI Annual 2026, someone asked on LinkedIn how many leads sponsors got from the event. Steve Burton, CMO of Aurasell, answered in one line: “Don’t count leads, but we booked 85 meetings on the calendar.” Aurasell’s CMO That’s the right way to measure an…
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If Your CRO, CCO or CPO Doesn’t Meet With Customers Their First Week On The Job … Move On. Apologize, But Let Them Go.
"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……
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Dear SaaStr: How Do I Find Product Market Fit In the Early Days?
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…
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Dear SaaStr: Do VCs Want To Talk To Senior Execs That Quit a Portfolio Company?
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,…
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7+ Tips On How To Build Your First Sales Team. When You Have Zero Experience Building One.
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…
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The #1 Mistake I See Founders Make When They Hire Their First VP of Sales
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…