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We Haven’t Had a Great CS Experience in Years. But Our FDEs Have Been Incredible.
May 14, 2026
In some ways, we helped build the Customer Success category at SaaStr a generation or so ago. Some of the earliest writing here on Second Order Revenueand the power of a funded, dedicated CS organization informed a generation of B2B founders. We believed in it deeply....
Dear SaaStr: Should a Startup Founder Handle Sales Themself When First Getting Started?
May 14, 2026
Dear SaaStr: Should a Startup Founder Handle Sales Themself When First Getting Started? The answer is yes - 95% of the time. The “best” sequence for building a repeatable sales engine is roughly: The CEO/founder should close at least the first 10 (or 20 or whatever)...
Don’t Be a “Woe is Me” Founder. That’s Always a Recipe for Failure. Especially Now, In The Age of AI
May 14, 2026
The frenetic pace, competition ans cale in the Age of AI is leading to a lot of folks to say ... Woe is Me: "It's so hard." "It's not our fault." "Well, we'll try." "No one wants our product." "The market changed on us." "AI killed our category." "Our biggest...
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Blog Posts, Customer Success
We Haven’t Had a Great CS Experience in Years. But Our FDEs Have Been Incredible.
By Jason Lemkin | May 14, 2026
In some ways, we helped build the Customer Success category at SaaStr a generation or so ago. Some of the earliest writing here on Second Order Revenueand the power of a funded, dedicated CS organization informed a generation of B2B founders. We believed in it deeply. So it’s not without some sadness that I say…
Continue Reading
Blog Posts, Early, Leadership, Q&A, Sales
Dear SaaStr: Should a Startup Founder Handle Sales Themself When First Getting Started?
By Jason Lemkin | May 14, 2026
Dear SaaStr: Should a Startup Founder Handle Sales Themself When First Getting Started? The answer is yes – 95% of the time. The “best” sequence for building a repeatable sales engine is roughly: The CEO/founder should close at least the first 10 (or 20 or whatever) customers. That way, she knows. She knows the process,…
Continue Reading
Blog Posts, Early
Don’t Be a “Woe is Me” Founder. That’s Always a Recipe for Failure. Especially Now, In The Age of AI
By Jason Lemkin | May 14, 2026
The frenetic pace, competition ans cale in the Age of AI is leading to a lot of folks to say … Woe is Me: “It’s so hard.” “It’s not our fault.” “Well, we’ll try.” “No one wants our product.” “The market changed on us.” “AI killed our category.” “Our biggest customer churned and there’s…
Continue Reading
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Aaron Levie, CEO and Co-Founder of Box

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Lew Cirne, CEO of NewRelic

"SaaStr is the undisputed thought leader in how to build SaaS businesses. Jason is legendary."
Lew Cirne, CEO of NewRelic

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Scott Dorsey, CEO of ExactTarget

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Popular Q&A
Dear SaaStr: What Was the Toughest Rejection You Ever Had in Sales?
Oct 26, 2025
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?
May 10, 2025
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
Feb 28, 2025
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
Feb 19, 2025
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?
Dec 9, 2024
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
Apr 19, 2024
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


