Selling the Cloud delves into the stories of C-suite veterans in Sales, Marketing, Customer Success, and RevOps, revealing the secrets behind building successful SaaS empires. Each episode features seasoned leaders who walk through their career journeys, sharing the wins and lessons learned along the way. From mastering customer acquisition to leveraging AI-powered marketing and sales strategies, our guests provide actionable insights for driving growth and business success in the B2B SaaS space.
Guided by a powerhouse team of co-hosts, including Mark Petruzzi, Paul Melchiorre, and Kristin "KK" Anderson, Selling the Cloud offers a front-row seat to the evolving world of Go-To-Market strategies. This podcast extends the insights from the best-selling books "Selling the Cloud" and "Data and Diagnosis-driven Selling", co-authored by Mark Petruzzi and Paul Melchiorre, making it your go-to source for the latest trends and practical tips in SaaS excellence.
In this Part 2 episode, co-host Mark Petruzzi continues the conversation with Jack Zimnavoda, Head of Customer Success at Insightful. This time, they explore how Jack’s team is scaling Customer Success by embedding AI, aligning post-sale marketing, and applying smart segmentation strategies.
Jack shares how predictive tools, data-informed health scores, and hybrid touch models enable CS teams to identify churn risks, streamline workflows, and drive expansion; all while maintaining a personal touch.
What You’ll Learn
- Predictive CS in Action: Jack explains how his team uses AI within their CS platform to surface risk, recommend proactive next steps, and highlight expansion-ready accounts.
- Marketing + CS = Growth: How Insightful brings CS and marketing together to educate customers, promote feature adoption, and scale communication—without losing personalization.
- Segmentation for Scale: Why Insightful uses a hybrid touch model to support over 5,000 customers across different industries and sizes—without compromising value delivery.
- Retention Forecasting: Discover how qualitative inputs, usage data, and AI models combine to anticipate churn and improve long-term customer outcomes.
Key Topics
- Building a predictive, AI-supported CS platform
- Aligning CS, product, and marketing post-sale
- Hybrid-touch models for scale
- Customer health scoring and churn prediction
- Operationalizing expansion strategy
- Creating scalable CS motions with a human touch
Guest Spotlight: Jack Zimnavoda
Jack is Head of Customer Success at Insightful, where he leads global efforts in retention, adoption, and expansion. With over 10 years of experience in B2B SaaS, Jack has developed practical, scalable strategies that connect Customer Success with revenue growth.
Resources & Mentions
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