Why the Markets Hate GTM the Most

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 apps and compared them with infrastructure and security. GTM software trades at a fraction of what infra and security trade at, and in several cases the growth rates are the same.

Multiples below are enterprise value over trailing twelve months revenue, at mid-October closing prices. Growth is year-over-year revenue growth in each company's most recent reported quarter.

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, Rory O'Driscoll and I went through what's actually in it, the one number Rory finds scary, and the number I think is worse that isn't in the filing at all.

From there we got into Microsoft offering exits to more than a quarter of its company,

The bill for AI capex coming due in 2027,

A Qwen model trying to reach a server in Beijing, and

A mock investment committee where Harry wanted Instinct at $30B and I wanted to put 20% of the fund into OpenAI.

How the best software platforms are keeping their customers for good

Most platforms leave 80% of their customers exposed. The best are reducing that number below 30% while also growing revenue. Here's how they do it.

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 annual contracts. I felt like when I was a B2B CEO and had to go profitable, they helped saved my rear. Close, say, a $125k contract, even after a healthy sales commission, that's $100k+ in the bank right now! And if your burn rate is low (ours was probably $100k-$150k at the time we started to close bigger annual deals), that's like a whole extra month of runway just on that deal. A multi-year pre-paid contract can be even more magical, and give you months of extra cash in a start-up.

This edition of the SaaStr Daily is sponsored in part by Fathom

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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 ARR.

Fiscal 2026 closed July 31. ARR was $1,237 million at current exchange rates, up 19% in constant currency, and fully ramped ARR was $1,573 million, up 22%. Total revenue was $1,475.4 million, up 23%. Subscription and support grew 33% and license revenue fell 7%. The CFO said ARR gross attrition was the lowest since Guidewire began measuring ARR, and operating cash flow margin was 26%.

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:

B2B & AI Markets · Close: 2026-10-30

The Latest on The Agents

Is AI Actually Recommending You? How to Get Picked by Agents | The Agents #17

Amelia and Jason delve into Agent-Led Growth, discussing how to ensure your business is recommended by AI agents. They cover the importance of first-party data, competitor tracking, and the new discipline of Agent Experience Optimization to enhance outbound strategies.

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