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Artificial Intelligence (AI), Blog Posts, SaaStr.Ai
We’ve Deployed 20+ AI Agents. Here Are the 10 Mistakes Almost Everyone Makes
We’ve now deployed 20+ AI agents at SaaStr. We run an eight-figure business on 3 humans and a fleet of agents. We’ve sent 100,000+ hyper-personalized outbound emails, booked hundreds of meetings automatically, had 2.75 million conversations through our AI advisor, and generated real, closed-won millions of revenue from AI agents that work at 6:02pm on…
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5 Interesting Things, Blog Posts, Scale
5 Interesting Learnings from Samsara As It Reaccelerates at $1.9 Billion in ARR
So Samsara just closed out its fiscal year 2026, and while the vertical B2B leader has always been a rocketship, it’s now showing reacceleration to 30% growth as it crosses $2 Billion in ARR. There’s several reasons as we’ll dig into below, but AI is on the list. And in a time when the markets…
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Blog Posts, Early
3 Things That Are Hard to Recover From. And 3 Tough Things You Bounce Back From Stronger.
Things you think are hard to recover from: – Losing a top customer– Not getting VC funding– Competitor winning key deal Things that are actually hard to recover from: – Wrong co-founder– Wrong key VP hire– Wrong largest VC — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) April 22, 2021 As a founder in the early days, and…
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"SaaStr is the largest community of people who like enterprise software on the planet. It’s a great community of people trying to build companies and learn from one another. It’s pretty amazing to see."
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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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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