Summary

Most employees don't think about their benefits until something goes wrong—and by then, they've already forgotten the open enrollment presentation, the brainshark, and the guide they skimmed in October. 

In this episode, Kelsey Willock sits down with Chloe Jones, Executive Director of Global Benefits at CACI International, for an honest conversation about where benefits delivery actually breaks down and what it takes to reach people when it matters. 

Chloe's path into benefits started with a serendipitous lunchroom friendship at a small insurance brokerage—a colleague she'd chatted with for a year wrote her an unsolicited recommendation on the way out the door, and Chloe got the job that launched everything. That story tells you a lot about how she thinks: relatable, generous, and grounded in the reality that most people don't grow up learning how money works.

 She and Kelsey get into why benefits communication has to happen everywhere all year (not just at enrollment), why employees won't tell you they don't understand the information, how AI is about to reshape benefits navigation while raising serious data privacy questions, and what at-home diagnostic kits could mean for the future of preventative care. If you design, deliver, or communicate benefits programs, Chloe's perspective on meeting employees where they actually are—not where you assume they are—will sharpen how you think about the work.

Timestamps

• 00:16 – Chloe's winding path from history degree to global benefits leadership
• 06:17 – First job at Limited Too and the first paycheck that went straight to a manicure
• 07:16 – Why Chloe has no earliest memory of money—and what that says about financial education
• 10:26 – How humble beginnings shaped her approach to employee communication
• 14:22 – Where benefits break down: the delivery gap between enrollment and real life
• 18:23 – AI, PII, and the tension between personalization and data privacy
• 21:00 – At-home diagnostic kits and what's coming next for the employee experience

Takeaways

• Open enrollment gets people enrolled—it doesn't teach them how to use what they have; the real work happens all year long
• Employees wear work masks and won't tell you they don't understand the information; you have to communicate across every channel, not just the one that fits your company's "look and feel"
• Frame benefits so people can find what they need in the moment they need it, not just when you're ready to present it
• Financial education is missing from most people's upbringing; staying relatable in how you communicate isn't optional, it's the job
• Watch the intersection of AI-powered benefits navigation and data privacy closely—legislation is coming, and your contracts need to be ready

Guest LinkedIn: https://www.linkedin.com/in/chloe-jones-5a60556b/

Company website: https://www.caci.com

Sponsor

Aura Finance helps you simplify compensation and benefits planning by bringing everything into one streamlined platform. No more juggling spreadsheets, disconnected tools, or manual calculations

Aura gives you a single place to design, compare, and communicate total rewards packages with confidence.

With AIpowered insights, it takes the guesswork and busywork out of comp decisions, helps you spot pay equity gaps early, and makes it easy to model scenarios that keep your teams engaged and your budgets on track.

See a demo at https://www.aurafinance.com/

• (00:16) - Chloe's winding path from history degree to global benefits leadership