5 Interesting Learnings from Stripe at $6.8 Billion in Revenue: 33% Growth, 47% Free Cash Flow Margins, and a $53B Bid for PayPal
Stripe is still private, so we mostly get data when the company chooses to give it to us. This week we got more than usual. The Information reported Stripe’s 2025 revenue hit $6.8 billion, up roughly a third year-over-year, its fastest growth since 2021. Free...
The Sub-5% Club: The Terminal State of Software
For twenty years, the slow lane in B2B wasn’t great. But it was an OK place to be. Growth faded, but the annuity was forever. High NRR, high margins, sticky contracts, structured data that was stuck in an app and couldn’t leave, predictable cash. You...
5 Interesting Learnings from Zoom at ~$5 Billion in ARR: Modestly Re-Accelerating Growth, Real AI Monetization, a $27B Market Cap, and a 25x Anthropic Windfall
Almost everyone wrote Zoom off a few years back. The innovative app everyone loved before 2020, but then almost a COVID one-hit-wonder that peaked in 2021 after going from $1B to $4B in ARR in one year. That would slowly bleed out as people went back to the office...
Three $3B B2B Acquisitions in 30 Days: Intercom/Fin, Cognite, and MaintainX. They All Bought the Same Thing: Data for AI
Three $3B B2B Acquisitions in 30 Days: Intercom/Fin, Cognite, and MaintainX In about a month, three B2B companies recently were acquired for right around $3 billion each. On the surface they have nothing to do with each other: Salesforce bought Fin (the company...
5 Interesting Learnings from Vertical B2B Leader ServiceTitan at $1B+ in ARR. Not Slowing Down, Growing 25%, Fintech Growing Fastest, 110% NRR
ServiceTitan has somewhat quietly become one of the most important vertical software stories of the past decade. It sells an end-to-end operating system to the trades: HVAC, plumbing, electrical, roofing, garage doors. And it just crossed a $1B revenue run rate the...
By Year-End, Anthropic Will Out-Earn Every Public Software Company Except Microsoft
Our jaws drop at Anthropic’s growth rate, and its valuation. But sometimes we can lose sight of just how big it already is … versus everyone else in software. Anthropic exited 2025 at roughly $9 billion in run-rate revenue. By February 2026 it was $14...
5 Interesting Learnings from Toast at $6.5 Billion Run-Rate: 22%+ Growth, Profitable, No Deceleration. But AI Is Just Getting Started
AI Vertical SaaS is hot now. Toast is … a dominant vertical SaaS leader becoming AI-first. Toast is running at a ~$6.5 billion revenue run-rate. At its core Toast is a payments business, with a high-margin software business as a subset inside it, a fintech...
Figma Grows 46% and Trades at 6x. Everyone Else Growing 30%+ Trades at 15-36x.
Figma went public on July 31, 2025 at $33 a share, popped 250% on day one to close at $115.50, and got valued near $68 billion. It peaked at $142.92. This week it trades around $19, with a market cap near $10 billion. That is down roughly 87% from the high. Down about...
Why Navan Is Up +30% in 2026. When So Many Other Public Software Leaders Are Down.
Pull up a chart of public B2B software in 2026 and it is a sea of red. IGV, the iShares software ETF, is down more -15% year-to-date and off roughly 30% from its September 2025 peak. For the first time in history, software forward multiples dropped below the S&P...
Adobe Just Deferred a Big Annual Price Increase. It’s the First Big Crack in B2B Pricing Power Since 2022.
For four years straight, the B2B playbook has been the same. Raise prices every 12 to 18 months. Add an AI SKU you have to pay extra for (another price increases, really). Customers grumbled and paid, because where else were they going to go. They were locked in. It...
Salesforce at 2.8x ARR, HubSpot Down 56%, Adobe at 11x Earnings: Are They Just Too Oversold Now?
Four months ago the markets decided B2B software was dead. In a 48-hour stretch in February, roughly $285 billion in software market cap evaporated. The trigger was the fear that AI agents would make per-seat licensing obsolete, that the entire model of charging...
Snowflake’s CMO Runs Marketing for 700 People. She Starts Her Day By Talking to Her Data, Not a Dashboard.
Denise Persson runs marketing for Snowflake. That’s a 700-person org, new-business pipeline she’s personally accountable for, and a level of compliance and data risk most of us never have to think about. She came back to SaaStr AI 2026 to talk about what...
Shopify Turns 20! 5 Interesting Learnings from Shopify at $13B+ in ARR. And Accelerating
hopify just turned 20. The company Tobi Lütke spun out of a snowboard shop called Snowdevil in 2006 is now processing more than $100 billion of merchant sales in a single quarter and running at a $13B+ revenue run rate. Most software companies that old are coasting on...
Don’t Let Them (Your Best Employees) Go
When you see Founder Mode from a non-founder When you find a VP, an exec, that actually cares as much as a founder, or almost as much … Promote them fast. ASAP. Double their equity. And … never let them go. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) May 29, 2026 It...
Founder SaaStr
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