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Outbound Always Works. If You Do It Right. And You Put In The Time.
Jun 21, 2025
https://twitter.com/jasonlk/status/1885289927555858504 These days, it can really feel like the Old Bag of Sales Tricks is starting to just not work anymore: With maybe 500x the SaaS vendors of 10 years ago, there's so much noise. Emails get blocked, spam filtered. AI...
Dear SaaStr: What Should I Know As a First-Time Customer Success Manager?
Jun 21, 2025
Dear SaaStr: What Should I Know As a First-Time Customer Success Manager? As a new Customer Success Manager (CSM), here’s what you need to know to hit the ground running and make an impact: Understand Your Role’s Revenue Impact -- Revenue vs Retention: Customer...
The $14.8B AI Deal That “Makes No Sense,” IPO Pops, and Why Legacy B2B is Stuggling: The Latest SaaStr + 20VC Breakdown
Jun 20, 2025
The State of AI Acquisitions, IPO Markets, and Venture Capital: Key Takeaways from the Latest 20VC + SaaStr Episode The latest 20VC podcast brought together venture veterans Rory O'Driscoll, Harry Stebbings, and Jason Lemkin for a wide-ranging discussion covering the...
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Outbound Always Works. If You Do It Right. And You Put In The Time.
By Jason Lemkin | June 21, 2025
"Crummy outbound may not work that well these days. But great outbound still works like magic." pic.twitter.com/DwjcgRLOVA — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) January 31, 2025 These days, it can really feel like the Old Bag of Sales Tricks is starting to just not work anymore: With maybe 500x the SaaS vendors…
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Blog Posts, Q&A
Dear SaaStr: What Should I Know As a First-Time Customer Success Manager?
By Jason Lemkin | June 21, 2025
Dear SaaStr: What Should I Know As a First-Time Customer Success Manager? As a new Customer Success Manager (CSM), here’s what you need to know to hit the ground running and make an impact: Understand Your Role’s Revenue Impact — Revenue vs Retention: Customer Success isn’t just about keeping customers happy anymore at most B2B…
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Blog Posts
The $14.8B AI Deal That “Makes No Sense,” IPO Pops, and Why Legacy B2B is Stuggling: The Latest SaaStr + 20VC Breakdown
By Jason Lemkin | June 20, 2025
The State of AI Acquisitions, IPO Markets, and Venture Capital: Key Takeaways from the Latest 20VC + SaaStr Episode The latest 20VC podcast brought together venture veterans Rory O’Driscoll, Harry Stebbings, and Jason Lemkin for a wide-ranging discussion covering the biggest stories shaping the enterprise software and AI landscape. Here are the essential insights every…
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Aaron Levie, CEO and Co-Founder of Box

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Lew Cirne, CEO of NewRelic

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