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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
Rippling Ran 2,100 Scored Agent Runs Per Model on Real Payroll Data. The Cheapest Model Tied the Most Expensive One.
Rippling Tested 15 AI Models on Real Payroll Data. The Cheapest One Tied the Most Expensive One. Rippling’s President and CPO Matt MacInnis published something most B2B companies have and almost none share: a real test of AI models doing real work inside a real production system. Not a leaderboard. Not made-up tasks. About 2,100…
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Blog Posts, Growth, Product, SaaS Product Pricing
On Your Next Big Deal? Double Your Pricing.
"Want to go upmarket? Then double your pricing on your next deal. Not on your existing customers. They bet on you. But if your biggest customer is $10k today, try charing $20k to the next one. You'll learn. Fast." pic.twitter.com/bVTHLO5pkM — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) August 18, 2026 There’s a fun — and very lucrative…
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Blog Posts, Q&A
Dear SaaStr: I Was Fired Without Cause. Should I Tell My Story Publicly?
Dear SaaStr: I Was Fired Without Cause. Should I Tell My Story Publicly? I get it. In a sense, it happened to me — once. But I’ve learned a few things: No one cares. They really don’t. It can make you look a bit petty or weak (fair or not). No one wants to work with, or…
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Aaron Levie, CEO and Co-Founder of Box
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Eric Yuan, CEO & Co-Founder of Zoom
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Lew Cirne, CEO of NewRelic
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Schmoozing Is Dead, Agents Are Hitting 120% of Humans, and Growth Is the Only Thing That Matters: 10 Things From the Closing Q&A at SaaStr AI Annual 2026
We just wrapped SaaStr AI Annual 2026, and the closing Q&A on Day 3 ended up being one of the most engaged of the whole gathering. No script, no prepared deck, just an hour-and-a-half of questions from the audience on the topics most on their mind....
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...
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