Building AI fluency internally and for customers

Cassie explains bringing AI into CS internally first, using monday.com's own agent tools and Vibe tooling.

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Heading to Vegas this May?

Join Josh at Pulse 2026 and come say hi—your oversized fluorescent daiquiri is on him. No catch.

Grab your ticket at gainsightpulse.com and use code UNCHURNED for a special rate.

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