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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
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 differences are becoming stark—not just in product, but in how they operate,…
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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
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 AgentForce, an inbound meetings booker in Qualified, a content…
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5 Interesting Things, Blog Posts, Scale
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 you’re building a B2B or B2B + AI company right now. 1….
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Lew Cirne, CEO of NewRelic
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Aaron Levie, CEO and Co-Founder of Box
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Dear SaaStr: What Was the Toughest Rejection You Ever Had in Sales?
Dear SaaStr: What Was the Toughest Rejection You Ever Had in Sales? The hardest rejection I’ve had in sales was around renewals. Especially ones I thought we really had earned. But still lost. In particular, in the early days of EchoSign / Adobe Sign, we had a...
Dear SaaStr: What Is the Playbook for a Successful Customer Success Team?
Dear SaaStr: What Is the Playbook for a Successful Customer Success Team? A good playbook for customer success is all about driving retention, expansion, and customer happiness while making it scalable: Hire Truly Product-Savvy Customer Success Managers at First Focus...
AI at Scale: 8 Learnings from monday.com Co-Founder and Co-Ceo Eran Zinman
monday.com Co-CEO and Co-Founder Eran Zinman recently sat down with SaaStr CEO and Founder Jason Lemkin to share his insights on their journey, including how they’ve leveraged AI, maintained growth, and expanded into multiple product lines.
The 2025 SaaS Vibe Check: What Founders Need to Know Right Now with SaaStr CEO and Founder Jason Lemkin
SaaStr CEO and Founder Jason Lemkin did a vibe check into the state of SaaS, AI, venture funding, and the rollercoaster of building a business in 2025.
Dear SaaStr: Can an Entrepreneur Back Out of a Signed Term Sheet Without Damaging Their Reputation?
Dear SaaStr: Can an entrepreneur back out of a signed term sheet without damaging their reputation? In my experience — Yes, probably. As a founder, you can back out of a term sheet if something is off, or even if you just get another offer you prefer. There is a lot...
How To Reverse-Engineer a $100M Exit: SaaStr on My First Million Pod
How do you reverse-engineer your first million as a SaaS startup founder? SaaStr founder and CEO Jason Lemkin chats with Sam Parr on the popular YouTube channel and podcast My First Million about what’s required to make it on the map for a $100M exit and then reverse engineers the steps to get there.
Rule 1: New minimum is $400K per employee
Rule 2: Go multi-product
Rule 3: Your second product must be bigger than your first product
Cheat code: Double your prices
Rule 4: 30% of your revenue is international
Rule 5: Localize your product
Cheat code: Remove friction
Rule 6: 100% net revenue retention
Rule 7: Don’t raise double digit millions
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