Cassie Young brings hard earned lessons from a career spanning CRO roles, customer success leadership, turnarounds, and now investing as a General Partner at Primary Venture Partners. She talks about building and rebuilding go to market teams, why sometimes you should fire customers on purpose, and how churn is a lagging indicator that hides deeper retention issues. Cassie shares strong views on overrated metrics like NPS, the incentives that actually drive behavior inside a business, and the myth of finding one perfect KPI. She also brings signature Cassie isms like sunlight is the best disinfectant and the reminder that leaders often get stuck working in the business instead of on it offering practical insights for anyone trying to keep their SaaS metrics from going sideways.

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SPONSORS:

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Mercury is business banking built for builders, giving founders and finance pros a financial stack that actually works together. From sending wires to tracking balances and approving payments, Mercury makes it simple to scale without friction. Join the 200,000+ entrepreneurs who trust Mercury and apply online in minutes at https://www.mercury.com

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Tipalti automates the entire payables process—from onboarding suppliers to executing global payouts—helping finance teams save time, eliminate costly errors, and scale confidently across 200+ countries and 120 currencies. More than 5,000 businesses already trust Tipalti to manage payments with built-in security and tax compliance. Visit https://www.tipalti.com/runthenumbers to learn more.

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LINKS:

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

Primary Venture Partners: https://www.primary.vc/

CJ on LinkedIn: https://www.linkedin.com/in/cj-gustafson-13140948/

Mostly metrics: https://www.mostlymetrics.com

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RELATED EPISODES:

Getting fired 4 times made me a founder | Sam Jacobs of Pavilion

https://youtu.be/8X-JVOF-1A0

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TIMESTAMPS:

00:00:00 Preview and Intro

00:02:30 Sponsors Aleph | Fidelity Private Shares | Sage Intacct

00:05:21 Returning From Pavilion & GTM Summit Takeaways

00:06:49 What Makes a Great Executive

00:11:07 The Importance of True P&L Fluency

00:12:17 First Team Leadership vs Functional Loyalty

00:13:33 Reading the Macro Environment and Market Forces

00:14:29 Sponsors Mercury | RightRev | Tipalti

00:18:26 Applying First Team Leadership in Practice

00:22:24 Churn as a Lagging Indicator

00:24:23 Finding Real Leading Indicators of Renewal

00:25:30 Customer Value as the Only Path to Enterprise Value

00:26:52 Product Adoption Perception and Retention

00:29:16 Price to Value Ratio as a Predictor of Guaranteed Churn

00:30:37 The Ultimate Question What Gets Your Customer Promoted

00:32:33 How NPS Is Actually Calculated

00:34:56 Sailthru’s Minus 26 NPS and What It Signaled

00:37:31 Rebuilding Customer Trust Through Transparency

00:40:24 Why Net and Gross Retention Must Be Paired

00:42:51 Aligning the Executive Team Through a Unified Bonus Plan

00:45:18 Firing Customers When Misaligned Segments Drain the Org

00:49:35 Carrot vs Stick How to Motivate a Modern GTM Org

00:52:31 Why MBO Plans Fail CSMs

01:03:51 Why Time to Value Matters More Than Ever

#RunTheNumbersPodcast #CustomerSuccess #ChurnPrevention #GoToMarket #VentureCapital

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit cjgustafson.substack.com

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