DigitalOcean? It’s Up 12% in 2026. While The Rest of Software Is Down 24%. Here’s Why.
The IGV software ETF just entered a bear market. ServiceNow is down 50% from its highs. Salesforce and Workday have been crushed. And somehow, the little developer cloud that everyone wrote off is one of the only winners left standing. Let’s set the scene. It is...
The Boomerang Founders: Why UiPath and Workday’s Creators Had to Come Back — And Who’s Next
When AI threatens to eat your company, only the founder can rewrite the menu. There’s a moment in the life of every successful B2B company where the founder steps back and says: “I built this thing. It works. Let the professional operators take it from...
SaaStr AI App of the Week: Lightfield — The AI-Native CRM That Updates Itself, Preps Your Meetings, and Actually Knows Your Customers Cold
The Bottom Line: Lightfield is the AI-native CRM built by the founders of Tome — the presentation tool that hit 25 million users and raised $81M from Coatue, Greylock, Lightspeed, 8VC, and GV at a $300M valuation. CEO Keith Peiris and CPO Henri Liriani (both ex-Meta,...
The Painful Gaps Between AI-Native and Traditional B2B Startups Today. Here’s a Checklist To Help. Which Are You … Really?
Anyone investing (including me) has been spending a lot of time with both AI-native startups and traditional B2B companies lately. We see what the newcomers are doing, what the hypergrowth players are doing, and how the incumbents are handling the AI Age. The...
The Agent Orchestration Problem: How We Wire 20+ AI Agents Together Without Losing Our Minds
Most of the AI agent content out there follows the same script: we deployed an AI SDR, here are the results, wasn’t that amazing. Nobody talks about what happens when you have multiple agents. When you have an AI SDR in Artisan, another one in Salesforce...
Stripe’s Latest Data: Startups Are Growing 50% Faster, Compute Demand Drove ~50% of GDP Growth, 60% More Apps YoY, and More
Stripe just released its 2026 annual letter, and as always, it’s packed with data. But a lot of the letter covers stablecoins, agentic commerce protocols, and macro-economic commentary. All interesting — but let me pull out the 5 metrics that matter most if...
The Wave of AI Agent Churn To Come: Prompts Are Portable
I was in a board meeting last week for a breakout AI B2B leader at $100m+ ARR and the team was excited … but stressed. Why? So many of their largest customers were happy to sign relatively large checks for their AI Agent. Six figures. Some even seven. The product was...
The 2025 IPO Class, Graded. Only 3 of 13 Are Above Water
Everyone said 2025 was the year the IPO window reopened. And technically, it did. 174 companies raised over $31 billion in the first half alone — the highest since 2021. But here’s what nobody wants to talk about: most of the B2B and tech IPOs from 2025 are now...
What’s It Really Like to Be CEO of a Startup
Dear SaaStr: What’s It Really Like to Be CEO of a Startup? Let me just throw out a few things I’ve learned that being a CEO of start-up isn’t, or isn’t as you’d expect: It isn’t glamorous until you are At Scale and Hot, at the very minimum. At...
Don’t Love Your Job? I Hear You. But Don’t Quit. At Least, 99% of You Shouldn’t.
I get it. A lot of jobs in tech just aren’t that rewarding anymore. If they ever were. At least in 2021, they were kind of easy, and you got to work from home, often < 30 hours a week. These six figure jobs honestly aren’t all that great, in many...
AI Agents in Sales and Finance Aren’t Behind. They’re Just Next. The Latest Data from Anthropic and ~1,000,000 Tool Calls.
Anthropic just published a breakdown this week of where AI agents are actually deployed across nearly 1 million real production tool calls. Software engineering sits at 49.7%. Sales and CRM is at 4.3%. Finance at 4.0%. Legal at 0.9%. At first it might seem to say AI...
SaaS Isn’t Dead. But the Way You Used to Win in B2B? That’s Gone.
There’s been a massive SaaS sell-off since mid-2025. Multiples compressed. Growth stocks punished. The “SaaS is dead” takes are everywhere again. B2B isn’t dead. Software is still eating the world. Businesses still need tools. Enterprise...
Canva Crosses a Stunning $4B ARR, Growing 35% (!). But What Would It Be Worth Today?
Canva just reported $4 billion in ARR per TechCrunch. And per COO Cliff Obrecht, it’s growing a stunning 35% $23M in 2018. $4,000M in 2025. 173x in seven years. It’s one of the most extraordinary B2B growth stories ever built — and it barely gets the...
Is SaaS Dead? No. But One Thing Is Clear: It’s Unstable.
For most of the past decade-plus, B2B software had a beautiful, almost boring stability to it. You’d build a product. You’d get it to $1M ARR. Then $10M. Then $100M. And the product you were selling at $100M ARR looked … pretty much the same as what you...
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