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Jason’s Takes on This Week’s 20VC x SaaStr: Pro Rata Fights, the First Real AI Price Drop, and Why $500M ARR Isn’t Safe Anymore
The SaaStr-side lessons from Valar, Jev, Haiku 5.5, Airtable and the Decacorn boom #1. Got cut out of a round? Say it once, then drop it. Years ago I was the only investor in a company for years. I bridged it when no one else would and helped wherever I could. Then a round came…
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Blog Posts
Just How Long Does The Average CMO and CRO Last? The Data From 14,000 Execs
49.7% of execs changed jobs in the last 16 months. 63% of CMOs turned over, says Jason Lemkin. "We have to constantly enrich our data because our buyers… turn over so fast that they're usually not there by the next." Your champion is already gone. pic.twitter.com/xYZiFyxPVN — SaaStr.ai (@saastr) October 12, 2026 Do your CMO…
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Blog Posts, Early, Growth, Hiring, Q&A
Dear SaaStr: What Role Do Founders Play Once They Hire an Outside CEO?
Dear SaaStr: What Role Do Founders Play Once They Hire an Outside CEO? Let me take a slightly different take on the question. Maybe you are really asking – “Am I still on the hook if we hire a ‘real’ CEO to run the company? ‘Cause I’m tired/stressed/don’t really enjoy running this thing. I’d rather…
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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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Popular Q&A
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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