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She went from treating eating disorders to running a $5M enterprise book at the biggest name in Customer Success and she didn't take no for an answer. Katy Bone, Enterprise CSM at Gainsight joins Josh to share the bathroom-humor pitch email that got her noticed, why vulnerability beats polish on LinkedIn, and the nonprofit born from unimaginable loss that's now reached families in 45 states.
Learn more or support the mission: https://www.blessingsforbarrett.com/
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What You'll Learn
- How a therapy background translates directly into churn prevention and relationship-building
- The exact outreach tactics Katy used to break into a competitive CS hiring process with a non CS background
- Why vulnerable, human LinkedIn content builds deeper trust with enterprise stakeholders than polished thought-leadership
- How cross-functional collaboration skills transfer from healthcare advocacy to CS
- The story behind Blessings for Barrett and how it's scaled using AI tools
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Timestamps
0:00 - Preview & Intro
0:48 - Meet Katy Bone, Enterprise CSM at Gainsight
1:27 - What an Enterprise CSM at GainSight actually does
2:15 - The Career Switch
5:02 - The parallel: fighting insurance denials vs. fighting churn
6:28 - Standing out against experienced CS candidates
7:47 - Sending a mock EBR prep before the interview
9:00 - The bathroom reading pitch email
10:28 - The LinkedIn banner that gets replies
12:02 - Learning it's okay to be vulnerable online
14:02 - What vulnerability has taught her about business
15:15 - Barrett's story & Blessings for Barrett
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Josh is writing a book on building customer relationships. Follow his journey and insights at www.joshschachter.com
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Where to Find the Guest
Katy Bone: https://www.linkedin.com/in/katy-bone-3b6334233/
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Where to Find the Hosts:
Josh's LinkedIn: https://www.linkedin.com/in/jschachter/
Unchurned Substack: https://unchurned.substack.com/