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Artificial Intelligence (AI), Blog Posts, Growth, SaaStr.Ai, Scale
ICONIQ: The 100%+ Growers Added 133% More Headcount in H1 2026. But The 50%-100% Growers Cut Hiring Almost in Half.
New ICONIQ data (as of 08/04/2026, covering 2022 through Q2 2026) on median headcount change by revenue growth band. ICONIQ’s own framing was that AI isn’t freezing headcount at hypergrowth companies, and that part is right. The more useful story is in the other three rows of the chart. N-size: 390 (2022-2023), 200 (2024), 195…
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Blog Posts, Career Growth & Advice, Growth, Q&A, Sales, Sales
To Really Scale, You Need $1M on Your Balance Sheet for Every $2M in ARR
"To really invest in your team, product, etc. you need at least $1 on the balance sheet for each $2 in ARR. At $20m ARR? You need $10m in the bank to make the hires, burn the tokens, etc. to really get to the next level. Below that … you hesitate." pic.twitter.com/Vdgzq0uKxC — Jason ✨👾SaaStr.Ai✨…
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Blog Posts, Q&A
Dear SaaStr: What’s the #1 Reason You See Sales Reps Fail These Days?
Dear SaaStr: What’s the #1 Reason You See Sales Reps Fail These Days? The #1 reason I see sales execs struggling today in new roles: they are convinced their playbook is better. And refuse to run the one that is already working. They are convinced they know better. That the founders are wrong, or whomever…
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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
"If you really want to be good at building up your company, read SaaStr."
Eric Yuan, CEO & Co-Founder of Zoom
"SaaStr is the undisputed thought leader in how to build SaaS businesses. Jason is legendary."
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
"SaaStr has pulled the entire SaaS community together in a powerful way."
Scott Dorsey, CEO of ExactTarget
"SaaStr is definitely the largest collection of people who like enterprise software — on the planet."
Aaron Levie, CEO and Co-Founder of Box
"SaaStr’s all about helping the younger founders be successful."
Phil Fernandez, CEO & Co-Founder of Marketo
"SaaStr is my peeps."
Dharmesh Shah, CTO of Hubspot
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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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