On the latest installment of Broken Benefits, Lee Lewis sits down with Jason Dinerman, VP of Product Development & Global Benefits at Mastercard, to explore what it really takes to create value — and just as importantly, visibility — inside a modern benefits operation.

Jason brings a rare blend of product thinking and global benefits leadership to the conversation. Drawing from his career journey, he shares how benefits leaders can move beyond administration and into strategic influence by clearly articulating impact, aligning with business priorities, and designing programs that are measurable, scalable, and understood.

The discussion dives into how benefits teams can reposition themselves internally — not as cost centers, but as value creators. Jason explains how applying product development principles to benefits strategy can unlock stronger engagement, clearer outcomes, and greater executive buy-in.

If you’re a CHRO, total rewards leader, or HR executive looking to elevate the strategic role of benefits within your organization, this episode offers a practical and forward-looking perspective on how to do it.

Chapters:

0:00 - Introduction

1:37 - Leading US Health & Well-Being at Mastercard

9:38 - The talent overlap between product development and benefits

17:14 - Designing benefits that people ultimately value

25:08 - Advice for today's benefits leaders

33:32 - Look inward for the most valuable data

39:00 - The future of transactions within healthcare

44:44 - How to connect with Jason

45:00 - Closing remarks