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...
Entrata at $575m ARR Growing 23% Is First of the Next Wave of PE-Backed Software IPOs. The Catch: Almost None of Them Are Accelerating.
Entrata filed its S-1 on May 28 to list on the NYSE under the ticker “ENT.” It’s the multifamily property management Operating System out of Lehi, Utah, founded way back in 2003, with Silver Lake holding majority control since 2022. The numbers are...
Salesforce Just Reaccelerated Growth at $45B+ ARR. It Took the Entire Kitchen Sink. 5 Learnings.
Reaccelerating growth at scale is the hardest thing in B2B. Almost no one does it. The law of large numbers is tough to defeat: the bigger you get, the more new revenue you need just to hold the same growth rate, and eventually the math wins. HubSpot, Workday, even...
Datadog Stock Is Up +66%. Here Are 5 Reasons Why, And Why It’s the Cleanest AI Beneficiary in B2B
Guess whose stock Is up +66% year-to-date? And trades at 20x ARR? In the midst of the most challenging run for software stocks … ever? Datadog. As of May 22, 2026: $222.32 per share, +66.20% year-to-date. Market cap: $79B. 52-week low was $98.01 just months...
Dropbox Hit $1B Faster Than Any B2B Company Ever. But Now, It’s The End of an Era
An end of an era Of my generation of SaaS CEOs, no star burned brighter than Dropbox It grew to $1B ARR faster than any before, and burning almost nothing, perfecting the PLG motion. The startup we all wished we founded. But in the end, there was no second act even...
5 Interesting Learnings from HubSpot at $3.5B in ARR: 23% Reported Growth, $211M in Buybacks, and a 16% Stock Drop
On paper, this was a strong quarter for HubSpot. Maybe not epic, but strong. HubSpot reported Q1 ’26 with revenue of $881M, up 23% … as reported. Subscription revenue alone hit $862.3M, putting ARR run-rate around $3.45B. They beat consensus by $18M....
Figma Beats, Raises and Accelerates! Boom! Stock Rockets 12%! But … It Still Trades for Less than 10X ARR
Figma reported Q1, and the results were the cleanest “beat and raise and accelerate” you’ll see all earnings season in B2B + AI. Revenue accelerated for the second quarter in a row. NDR ripped to a 2+ year high. AI monetization, which everyone on the...
5 Interesting Learnings from Monday at $1.4 Billion in ARR: Guidance Raised, Stock Crushes, NDR Up to 116%, But Real AI Revenue Still Ahead
Monday.com (MNDY) reported Q1 2026 this morning. The stock popped 28%+ in pre-market trading. In the same week, HubSpot reported a clean beat, and the stock dropped 16%. Both companies are application-layer B2B incumbents. Both have 250K+ customers. Both have AI...
The B2B Reacceleration Is Real, But Uneven. Twilio, Atlassian, Datadog, Cloudflare, and Palantir Just Proved It. HubSpot and Shopify Still Have To.
Seven of the most-watched names in public B2B reported in the last few days. Growth is back for many: Twilio just hit its highest growth in three years, from single digits to 20%+, and accelerating. Atlassian jumped to 32% and the stock ripped 30% in a day. Datadog...
Palantir Q1 2026 Has Broken the Enterprise Software Mold. Again. Revenue Growth Accelerates to 85% at $6.5B+ ARR
Three months ago we asked if Palantir might be the greatest enterprise software company ever built. The data said the question was at least worth asking. Today the question got harder to dismiss (especially if we don’t deem Anthropic an enterprise software...
Atlassian and Twilio Crush the Quarter, Accelerate. Is the SaaSpocalypse Over?
So this week two of the more important bellwether names in B2B software reported earnings. And neither of them just “beat.” Both accelerated. Materially. At $7B and $5.6B+ run rates respectively. They crushed the quarter, in fact. This really matters...
Dear SaaStr: What Sales Comp Plan Should I Use For Our Very First Sales Rep?
Dear SaaStr: What Sales Comp Plan Should I Use For Our Very First Sales Rep? At the end of the day you have to solve for two things: A plan that gives the reps a living, fair wage; and A plan that you know and feel is accretive to the company. Sales reps have to be...
Medallia Is Just the Opening Act: 12+ PE SaaS Deals With $50B+ in Debt at Risk of Blowing Up
Thoma Bravo handed the keys to Medallia over to its lenders yesterday. Blackstone, KKR, Apollo, and Antares are taking control of a company Thoma Bravo bought for $6.4 billion in 2021, wiping out roughly $5.1 billion in equity held by the firm and its co-investors....
Founder SaaStr
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