Fire bad customers save great ones | Cassie Young episode artwork

EPISODE · Dec 8, 2025 · 1H 11M

Fire bad customers save great ones | Cassie Young

from Run the Numbers · host CJ Gustafson

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.—SPONSORS:Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Sage Intacct is the cloud financial management platform that replaces spreadsheets, eliminates manual work, and keeps your books audit-ready—so you can scale without slowing down. It combines accounting, ERP, and real-time reporting for retail, financial services, logistics, tech, professional services, and more. Sage Intacct delivers fast ROI, with payback in under six months and up to 250% return. Rated #1 in customer satisfaction for eight straight years. Visit Sage Intacct and take control of your growth: https://bit.ly/3Kn4YHtMercury 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.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.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.—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—RELATED EPISODES:Getting fired 4 times made me a founder | Sam Jacobs of Pavilionhttps://youtu.be/8X-JVOF-1A0—TIMESTAMPS:00:00:00 Preview and Intro00:02:30 Sponsors Aleph | Fidelity Private Shares | Sage Intacct00:05:21 Returning From Pavilion & GTM Summit Takeaways00:06:49 What Makes a Great Executive00:11:07 The Importance of True P&L Fluency00:12:17 First Team Leadership vs Functional Loyalty00:13:33 Reading the Macro Environment and Market Forces00:14:29 Sponsors Mercury | RightRev | Tipalti00:18:26 Applying First Team Leadership in Practice00:22:24 Churn as a Lagging Indicator00:24:23 Finding Real Leading Indicators of Renewal00:25:30 Customer Value as the Only Path to Enterprise Value00:26:52 Product Adoption Perception and Retention00:29:16 Price to Value Ratio as a Predictor of Guaranteed Churn00:30:37 The Ultimate Question What Gets Your Customer Promoted00:32:33 How NPS Is Actually Calculated00:34:56 Sailthru’s Minus 26 NPS and What It Signaled00:37:31 Rebuilding Customer Trust Through Transparency00:40:24 Why Net and Gross Retention Must Be Paired00:42:51 Aligning the Executive Team Through a Unified Bonus Plan00:45:18 Firing Customers When Misaligned Segments Drain the Org00:49:35 Carrot vs Stick How to Motivate a Modern GTM Org00:52:31 Why MBO Plans Fail CSMs01:03:51 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

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.—SPONSORS:Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at https://www.getaleph.com/runFidelity Private Shares is the all-in-one equity management platform that keeps your cap table clean, your data room organized, and your equity story clear—so you never risk losing a fundraising round over messy records. Schedule a demo at https://www.fidelityprivateshares.com and mention Mostly Metrics to get 20% off.Sage Intacct is the cloud financial management platform that replaces spreadsheets, eliminates manual work, and keeps your books audit-ready—so you can scale without slowing down. It combines accounting, ERP, and real-time reporting for retail, financial services, logistics, tech, professional services, and more. Sage Intacct delivers fast ROI, with payback in under six months and up to 250% return. Rated #1 in customer satisfaction for eight straight years. Visit Sage Intacct and take control of your growth: https://bit.ly/3Kn4YHtMercury 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.comRightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit https://www.rightrev.com and schedule a demo.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.—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—RELATED EPISODES:Getting fired 4 times made me a founder | Sam Jacobs of Pavilionhttps://youtu.be/8X-JVOF-1A0—TIMESTAMPS:00:00:00 Preview and Intro00:02:30 Sponsors Aleph | Fidelity Private Shares | Sage Intacct00:05:21 Returning From Pavilion & GTM Summit Takeaways00:06:49 What Makes a Great Executive00:11:07 The Importance of True P&L Fluency00:12:17 First Team Leadership vs Functional Loyalty00:13:33 Reading the Macro Environment and Market Forces00:14:29 Sponsors Mercury | RightRev | Tipalti00:18:26 Applying First Team Leadership in Practice00:22:24 Churn as a Lagging Indicator00:24:23 Finding Real Leading Indicators of Renewal00:25:30 Customer Value as the Only Path to Enterprise Value00:26:52 Product Adoption Perception and Retention00:29:16 Price to Value Ratio as a Predictor of Guaranteed Churn00:30:37 The Ultimate Question What Gets Your Customer Promoted00:32:33 How NPS Is Actually Calculated00:34:56 Sailthru’s Minus 26 NPS and What It Signaled00:37:31 Rebuilding Customer Trust Through Transparency00:40:24 Why Net and Gross Retention Must Be Paired00:42:51 Aligning the Executive Team Through a Unified Bonus Plan00:45:18 Firing Customers When Misaligned Segments Drain the Org00:49:35 Carrot vs Stick How to Motivate a Modern GTM Org00:52:31 Why MBO Plans Fail CSMs01:03:51 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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Fire bad customers save great ones | Cassie Young

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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...

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