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What Would an Independent Slack Look Like If It Hadn’t Sold to Salesforce? And Would It Still Be Worth $27 Billion?
Julian Lehr asked a good question the other day on X: what if Slack had never sold to Salesforce, stayed in founder mode, and went hard at AI? What would the product look like, and what would it be trading at? What would an independent Slack look like today? Probably $2.5B ARR growing 25%, trading…
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Blog Posts, Sales
The First Week of a Great VP of Sales. And The First Month of a Mediocre One.
Great VP of Sales, first week: – brings 2-4 great sales execs in ASAP. often week 1– identifies top existing talent, does what it takes to keep them– begins to move out underperformers– jumps into all critical deals Mediocre VP of Sales, first month: – has no one to bring… — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk)…
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Blog Posts, Career Growth & Advice, Growth, Q&A, Sales, Sales
The CEO Never Gets to Step Away From Sales
"The #1 mistake founders make when they hire their first VP of Sales? Or even just their first sales rep? They step back from sales. No. You don't get that time back. It's just what you do in sales, changes." pic.twitter.com/wwUzRvrbt0 — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) July 29, 2026 Dear SaaStr: When Should The CEO…
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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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