Why Financial Wellness Programs Fail—and How to Fix Them

Why is financial wellness such a universally agreed-upon priority yet so painfully hard to deliver in practice? In this episode, I sit down with Jason Lee—founder of DailyPay, Salt Labs, and now Chief of Chime Enterprise—to break down why employees don’t engage with financial programs, why saving feels like the world’s most boring habit, and what it takes to design benefits that people actually use. Jason lays out why most employer programs are stuck in the 1980s, why rewards points sometimes function better than savings accounts, and why the best financial wellness programs should look less like coupon clubs and more like full-service hospitals—ER, diagnostics, and rehab floors included. We also explore how brand trust, design simplicity, and modern tech will shape the next generation of employee financial benefits. Related Links:Join the People Managing People community forumSubscribe to the newsletter to get our latest articles and podcastsConnect with Jason on LinkedInCheck out Chime Enterprise Support the show