When Rebecca Liebman took the stage for a panel on personalized workplace well-being, she pointed out something the audience hadn’t yet noticed: unlike her fellow panelists, she was holding a handheld microphone instead of wearing a clip-on. The reason was simple: clip-ons don’t attach well to dresses, and she’d asked for an alternative that worked for her. It was a small moment, but it captured the panel’s larger message. For years, employee benefits have been designed for one default kind of worker, and everyone else has been left to make it work anyway.

The panel at From Day One’s Chicago half-day benefits conference, brought together five benefits leaders for a wide-ranging conversation moderated by Kim Quillen, business editor at the Chicago Tribune. The discussion covered why generic benefits packages fall short, how data and communication strategy can close that gap, and what it takes to actually move the needle on employee engagement.

Meeting Employees Where They Are

Lara Johnson, senior director of employee growth and well-being at Netskope, a global cybersecurity company, says personalization at her company starts with acknowledging how different employees’ lives look. With a workforce spread across roughly three dozen countries and a limited well-being budget, her team built a “growth labs” program offering workshops on psychological safety and burnout, paired with platforms like LinkedIn Learning for professional development. The goal is to treat well-being and career growth as connected rather than separate priorities. “We believe when our employees grow, NetSkope grows,” Johnson said.

Joe Park, director of benefits at The Aspen Group, parent company of Aspen Dental, shared a story from earlier in his career that reshaped how he thinks about communication. A leader once told him about a family member who didn’t learn he had stage-four lung cancer until it was too late, a moment that pushed her team to stop sending the same “vanilla” wellness message to everyone. Instead, they hired a communications specialist, studied workforce demographics, and tailored messaging and visuals by audience. 

According to Park, engagement rose significantly within a year. “It’s about meeting people where they are,” he said. “It’s important to really look at your data, look at your population demographics, and think about how you personalize that to meet your workforce.”

Rahul Rajvanshi, director of benefits and total rewards at Montefiore Health System, framed the stakes in plain terms: a nurse working overnight shifts, a physician balancing patient care with family obligations, and a remote scheduler all need different things from their benefits. “We need to deliver benefits, what our employees want versus what is easy for HR administrators to admin,” Rajvanshi said. When Montefiore noticed physicians missing summer appointments because of childcare conflicts, the health system added dependent care and elder care benefits, and saw utilization of related services jump by half.

Holistic Wellness, With Budgets in Mind

Jane Lyons, SVP of customer success at SmithRx, a pharmacy benefit manager built around price transparency, says pharmacy benefits are often the most frequent point of contact employees have with their health plan, sometimes a dozen times a year, compared with an annual doctor’s visit.

That frequency, she says, makes every interaction an opportunity to educate members about cost-saving options, copay assistance, and alternative medications. “It’s really understanding where they are on their health literacy journey,” said Lyons. “We want to maximize those moments that matter.”

The same principle applies beyond healthcare: employees often need guidance not just in accessing benefits, but in making complex decisions about how to use them. Personalization and timely support can be just as critical when workers are navigating their financial lives. “Financial planning is just life planning,” said Rebecca Liebman, co-founder and CEO of LearnLux. “Financial well-being is just how do I want to live my life, and how can I put a plan together that makes sense for me.”

Two employees with identical salaries and debt loads might want completely different approaches: one focused on aggressively paying down debt, another comfortable investing while paying it off slowly. LearnLux’s certified financial planners field everything from questions about employee stock plans to urgent situations, like someone facing repossession of their car within days, says Liebman. When her organization rolls out programs across dozens of countries at once, the priority is offering consistent access to services while adapting the messaging to fit local financial norms and attitudes toward money.

The conversation around financial well-being also extends to healthcare spending, where rising costs are forcing employers to rethink how they support employees and manage expenses. Lyons of SmithRx also addressed the rise of GLP-1 medications for diabetes and weight management, noting that in some cases these drugs now account for roughly 30% of a company’s pharmacy spend. Pairing access to the medications with nutrition support and other wraparound services, she says, is essential to sustaining results.

Letting Data Guide the Strategy

Several panelists pointed to data as the foundation for personalization. Johnson described noticing a sharp spike in mental health service usage among Netskope’s Taiwan-based employees and tracing it back to an HR manager who had actively promoted the program. This finding helped the company refine its broader approach to reducing stigma around mental health support. Rajvanshi says Montefiore expanded its employee assistance program to round-the-clock availability after recognizing that nurses working overnight shifts couldn’t access support during standard daytime hours.

On reaching employees who don’t open benefits emails, panelists emphasized simplicity and channel diversity. Johnson says her team relies heavily on Slack to share curated updates, while Park encouraged stripping benefits jargon entirely. Johnson also runs an annual “Benefits 101” session that breaks down basic terms like deductibles and health savings accounts in plain language, which she said resonates especially with younger employees and those new to the U.S. health system.

Asked for a final piece of advice, the panelists largely agreed: start with data, not vendor pitches; treat well-being as inseparable from performance; and remember that the goal isn’t to hand every employee the same microphone—it’s to make sure they all have one that works for them.

Grace Turney is a St. Louis-based writer, artist, and former librarian. See more of her work at graceturney17.wixsite.com/mysite.

(Photos by Josh Larson for From Day One)