Summary

A hotel company with 120 properties across the country went from 20% open enrollment engagement to over 85% in a single year—and 21 properties hit 100%. The trick wasn't a new platform or a bigger budget. It was handing ownership to local leaders and a little friendly competition. In this episode, Kelsey Willock sits down with Brian Sosa, Director of Benefits at Crestline Hotels and Resorts, to talk about what actually moves the needle on benefits engagement when your workforce is scattered, multilingual, and rarely sitting at a desk. Brian brings a refreshingly analytical but human perspective to the work. He shares the story of buying a toy Hummer as a kid that taught him it's okay to spend money, how he invoiced his dad in dessert for his first "real" job, and how those early lessons shaped the way he designs tools and communications today. Kelsey and Brian get into why benefits break down most often (hint: it's not just communication), how to translate retirement contributions into "gallons of gas" so employees actually understand them, why sometimes launching the wrong thing is faster than running another survey, and where AI and care navigation tools may genuinely reshape the employee experience in the year ahead. If you lead a distributed workforce or just want sharper ideas for making benefits land, Brian's perspective is worth an hour.

Timestamps

• 00:48 The toy Hummer and the lesson that it's okay to spend
• 04:00 Brian's first "paycheck" paid in dessert by his dad
• 08:18 Where benefits break down: complication, not just communication
• 10:19 Translating retirement contributions into gallons of gas
• 12:37 The 120-property competition that drove 85%+ open enrollment engagement
• 16:31 Why the right benefits admin platform is really a data strategy
• 19:14 Launching things intentionally instead of waiting for survey results
• 21:24 Care navigation, AI, and what may actually shift the employee experience

Takeaways

• Make benefits language relatable — translate percentages into real-world dollars or something people already spend money on
• Hand ownership of engagement down to local leaders and add a little friendly competition
• Don't let survey fatigue stall you; sometimes launching the wrong thing surfaces what people actually need faster than asking
• Invest in data infrastructure, not just benefits programs — the insights shape next year's strategy
• Watch care navigation tools and AI closely; the real employee impact may be less about features and more about cost and access

Guest LinkedIn: https://www.linkedin.com/in/brian-sosa/

Company website: https://www.crestlinehotels.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 AI-powered 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/

• (00:48) - The toy Hummer and the lesson that it's okay to spend