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Their own customer research said restaurant owners feared AI. It was three months old and completely wrong Adam Guild CEO of Owner.com gave one of the more useful operator talks at SaaStr AI 2026 this year: three years of rebuilding Owner.com around AI, from a website and online ordering product for independent restaur
Every company cuts the same corner on renewals. You go top down. Your biggest accounts get a real custom deck with their actual results in it. Everyone else gets a templated follow-up email. Not because you don’t care about them. Because nobody has a week to build 25 custom decks, and the week you’d spend... Continue R
Linear published its tender offer news this week: $99 million of secondary at a $2.5 billion valuation, up from $1.25 billion at the Series C last year. Accel and 01A participated, with Salesforce Ventures and S32 coming in new. No primary capital raised. They’re cashflow positive with more cash in the bank than they’v
For about ten years, chief product officer was the best job in B2B. You brought your mug to the office, told the team what you were shipping this year, moved a few things to next quarter, and when an investor asked for a feature you said it was coming. And sometime, later, it was coming.... Continue Reading
New ICONIQ data (as of 08/04/2026, covering 2022 through Q2 2026) on median headcount change by revenue growth band. ICONIQ’s own framing was that AI isn’t freezing headcount at hypergrowth companies, and that part is right. The more useful story is in the other three rows of the chart. N-size: 390 (2022-2023), 200 (20
For the past six-plus months, almost no one at SaaStr has logged into Salesforce. The data is all still there. We still pay for it. We still depend on it. We just stopped using the UI as the primary way to get at any of it. Some context on why we did this. SaaStr runs... Continue Reading
Episode #013 of The Agents is here! Same setup as always: three humans, 20+ agents in production, an 8-figure B2B + AI business. This week was about what happens when agents take over the system of record. ServiceTitan just cut off Podium over exactly this question. Our own agents have written about 40GB into Salesforc
The CEOs I have the most respect for today? The ones truly rebuilding their companies for the Age of AI. Not just sort of, kind of, doing so. Not the ones who shipped AI features and put them on the pricing page. I mean the ones tearing up how the product works, how it’s priced,... Continue Reading
Kroll published its Summer 2026 Global Software Sector Update, covering software M&A and public comps through June 30, 2026. It’s 20 pages of deal data with a lot of detail on what the market currently pays for B2B software. The headline numbers read like a big M&A recovery. Deal volume is on track for the... Continue
Harry Stebbings, Rory O’Driscoll and I went through Nvidia’s ecosystem spending spree, OpenAI’s move from number one to number two, and what happens to CFO budgets when your best people are addicted to tokens. #1. Nvidia paid $6B for Poolside’s Model Factory, and the trigger was a $2B round that didn’t close Nvidia is.
Box reported Q2 FY27 and saw real if modest acceleration: Revenue of $321.1 million, up 9% and up 11% in constant currency. Non-GAAP operating margin of 29.4%. Non-GAAP EPS of $0.40 against a $0.39 guide. Free cash flow of $59.7 million, up 67%. Box is one of the cleanest live tests in public B2B of... Continue Reading
Dear SaaStr: My Sales Rep is Grossly Underperforming but is Involved in a Key Deal. Should I Fire Him or Wait for The Deal to Close? This is pretty common and most founders make the same mistake. Move on from the rep now. There is almost no chance he is adding value to the prospect... Continue Reading
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