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Blog Posts, Early, Q&A, Sales
Should You Hire a Sales Rep First, Or a Sales Manager?
Dear SaaStr: Should I Hire a Sales Rep First, Or a Sales Manager First? The ideal flow is: You (founder-CEO) close the first batch of customers, say the first 10 or 20. If you don’t, you’ll never really know how it’s done. Or be able to help anyone else, really. Then, once you know how to…
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Blog Posts
Jason’s Takes on This Week’s 20VC: Meet 100 VCs, None-and-Done Beats One-and-Done, and Build-to-Prod Is Where I’d Make 10 Bets
The deeper cut on a week where capital concentrated harder than I’ve ever seen, and what founders should actually do about it Harry, Rory and I covered a lot this week: a $20M ARR profitable company that can’t get a meeting, Anthropic’s $16.8B quarter, CoreWeave’s 25% drop, Modal at $15.75B, and Berkshire doubling down on…
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Blog Posts
Your Top Job For 2027: Hire 1-2 Execs Who Can Take the Load, Not Just Do the Work
I was with a great agentic B2B CEO this week, $100M+ ARR and still growing fast, and we got into hiring ex-founders. I’m a huge proponent. Every B2B company at scale should have 1 to 3 ex-founder CEOs on the team. They have superpowers you can’t train into an operator who has never been a…
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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
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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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