Summary
What do you do when the best benefits can't be justified by a spreadsheet? In this episode of Beyond the Paycheck, host Kelsey Willock Jones talks with Ann Meyers Piccirillo, CHRO of JDA TSG, about growing a company from 100 to 13,000 employees and building benefits for a workforce most benefits systems forget. Ann shares her case for strategic ROI alongside quantitative ROI, told through the surprise success of grandparent leave; the concierge healthcare experiment that went unused for two years and what its failure revealed about what employees really want; and the cafeteria-style healthcare plan she's building for seasonal workers, anchored in telehealth. A conversation for HR and benefits leaders who want to design for the people they actually employ.

Chapters

00:00 Introduction and meet Ann Meyers Piccirillo

01:45 A paper route and a first paycheck spent on candy

03:30 Opening doors for a seasonal workforce

06:45 Telehealth and building a cafeteria plan

09:45 Grandparent leave and meeting people where they are

12:00 Strategic ROI vs the spreadsheet

14:45 The benefits experiment nobody used

18:15 Positioning back office teams as revenue drivers

21:45 AI as a coworker, people as the differentiator

25:15 Tap yourself: don't wait for permission

Takeaways

-Strategic ROI belongs alongside quantitative ROI: benefits like grandparent leave cost money and return nothing measurable, yet convert into productivity, loyalty, and referrals over time.

-Fight for the benefits you believe in before the financial return shows up, because strategic return translates into financial return.

-A concierge discount healthcare package went essentially unused for two years because employees didn't want to be their own benefits broker; they wanted a traditional, trusted network model.

-Negative feedback is the clearest signal you'll get: people speak up loudly about what they don't like, and that clarity is shaping the next iteration of the benefits plan.

-For seasonal and hourly workers locked out of traditional coverage, a cafeteria-style plan anchored in telehealth plus validated point solutions can close the healthcare gap.

Connect with the Guest
LinkedIn: https://www.linkedin.com/in/annpiccirillo/
Website: https://www.jdatsg.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/