Why $100M AI Companies Are Failing at Renewals? ft. Cassie Young & Kyle Poyar

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Two of SaaS's most influential voices just sounded the same alarm: Cassie Young, General Partner at Primary Ventures, and Kyle Poyar, founder of Growth Unhinged, both published viral articles warning of a "gross retention apocalypse" in AI-powered SaaS.

Cassie's investigation revealed a shocking truth: when she called customer logos cited in AI fundraising decks, nine out of ten had already stopped using the product. Kyle's data showed founders bragging about hitting $10M ARR in a month with zero cohorts up for renewal.

In this conversation, they unpack why explosive growth often masks catastrophic churn, distinguishing between Annual Recurring Revenue and what Cassie calls "Experimental Recurring Revenue" - revenue that evaporates when customers realize the product doesn't deliver.

The discussion moves beyond diagnosis into what actually works. Kyle introduces forward-deployed engineering as a sales motion—getting customers live in production before they pay prevents churn better than any post-sales fix. Cassie argues we're entering a Customer Success Renaissance where the discipline evolves from reactive firefighting to strategic value delivery.

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Timestamps

0:00 - Preview & Introduction

1:36 - Meet Cassie Young & Kyle Poyar

3:00 - The Gross Retention Apocalypse & AI Churn Wave

7:25 - ERR vs ARR: The Red Herring - 9 out of 10 Customers Stopped Using

10:00 - Series A's Done on "Vibes"

11:05 - What Investors Are Looking For

14:40 - The Cluely Controversy: Distribution vs Product Quality

16:15 - Why Fast Growth Means Nothing Without Retention Data

21:15 - Customer Success as a Core Operating Philosophy

29:30 Forward Deployed Engineers as Part of Sales Motion

31:40 - Most Overrated Metric

32:08 - Most Underrated Metric

33:10 - SaaS Principles That Will Last 10 Years

35:30 - The Way Forward

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What You’ll Learn

* Why 9 out of 10 AI customers cited in fundraising decks have already churned

* The critical difference between ARR and ERR (Experimental Recurring Revenue)

* The "automatic pass test" top VCs use to evaluate startups in 60 seconds

* How to identify your north star usage metric for predicting churn

* Why distribution alone isn't enough (lessons from the Cluely phenomenon)

* How the Customer Success TAM could 10X if companies focus on the right things

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Where to Find Kyle Poyar:

LinkedIn: https://www.linkedin.com/in/kyle-poyar/

Substack: https://www.growthunhinged.com/

Podcast: https://podcasts.apple.com/us/podcast/mostly-growth/id1842238102

Where to Find Cassie Young

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

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Where to Find Josh:

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

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Resources:

Cassie's article: https://topline.beehiiv.com/p/tech-is-on-the-brink-of-a-gross-retention-apocalypse-a-customer-success-renaissance

Kyle's article: https://www.growthunhinged.com/p/the-ai-churn-wave