Cassie's Monday journey and rise to RVP

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CS is going through an identity crisis.

Is it product? Is it relationships? Is it revenue?

According to Cassie Vaughn (RVP of CS at monday.com)… it’s now all three, and AI is forcing it to be so.

In this episode of Unchurned, Cassie breaks down what’s actually changing inside modern CS orgs after scaling from CSM to leading a 100+ person team—and why most companies are still getting it wrong.

You’ll hear why “value” is still more storytelling than science, why health scores can’t be trusted, and why the future CSM won’t just manage customers… they’ll manage agents.

But here’s the twist: as AI automates more of the work, the human side of Customer Success is becoming even more critical. Monday.com is literally doubling down on time spent with customers—while everyone else is trying to scale it away.

Cassie also shares the bold bet they made: turning CSMs into revenue owners with variable comp—and why, in a consumption world, CS might actually be more commercial than sales.

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Timestamps

0:00 - Preview & Introduction

1:10 - Cassie’s journey from being a CSM to RVP

4:15 - What’s changed in CS over the last 6 years

6:13 - Why measuring customer value is still broken

9:35 - Why monday.com doubled time with customers

12:37 - The rise of the “agent manager” CSM

14:07 - Scaling CS with AI vs human touch

16:47 - Why CSMs are more commercial than sales

18:10 - Challenges of shifting to revenue ownership

19:30 - Why CSMs should think commercially & not trust health scores

21:50 - Stop being a generalist: career advice

23:26 - AI fluency as the #1 priority for 2026

25:25 - Lightning round: F1, food, and fun

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What You’ll Learn

* Why has no one cracked customer value measurement

* How to build value narratives that actually land with executives

* What AI should automate—and what should stay human

* Why the future CSM is an “agent manager”

* How monday.com is doubling customer time in an AI era

* Why CSMs should be more commercial than sales

* How to introduce variable comp for Customer Success

* Why health scores are not enough (and what to do instead)

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Want the playbook, not just the conversation? Subscribe for deep-dive, actionable breakdowns from every episode at unchurned.substack.com.

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Where to Find Cassie Vaughn

LinkedIn: https://www.linkedin.com/in/cassiebrown/

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Where to Find Josh:

LinkedIn: https://www.linkedin.com/in/jschachter/

Unchurned Substack: https://unchurned.substack.com/