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 episode, co-host Mark Petruzzi welcomes Jack Zimnavoda, Head of Customer Success at Insightful. Jack shares how modern B2B SaaS organizations can turn customer success from a support function into a true driver of revenue and retention.
Together, they explore what it takes to align CS with sales, marketing, and product—without creating channel conflict. Jack reveals how predictive AI, smart segmentation, and aligned incentives can turn expansion into a scalable and proactive motion.
What You’ll Learn
- Customer Success as a Revenue Driver: Jack explains how to reframe CS from a cost center to a growth engine—through structure, ownership, and incentives.
- Avoiding Channel Conflict: Learn how clearly defined swim lanes, compensation clarity, and collaboration between CS and Sales create harmony and momentum.
- Building a Scalable CS Model: From white-glove enterprise accounts to hybrid-touch models, Jack outlines how to maintain personalized value delivery at scale.
- Metrics That Matter: Understand the importance of net retention, lifetime value, and how CS teams can build pipelines and forecast revenue just like Sales.
- AI + Customer Health: Hear how Jack uses predictive AI to monitor product usage, signal risk, and surface expansion opportunities at scale.
Key Topics
- Structuring CS to own post-sale revenue
- Aligning CS, Sales, Marketing, and Product
- Channel conflict: where it happens and how to prevent it
- Using AI in CS forecasting and health scoring
- Segmenting your customer base to drive upsell plays
- Scaling without losing the human touch
- How to hire for commercial CSMs (hint: curiosity and creativity)
Guest Spotlight: Jack Zimnavoda
Jack is Head of Customer Success at Insightful, where he leads a global team focused on retention, adoption, and expansion. With over a decade of experience in B2B SaaS, Jack has helped transform CS into a proactive, commercial function that partners across the go-to-market org to drive real business outcomes.
Resources & Mentions:
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