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What’s keeping HR leaders up at night in 2026? We asked four of them…

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Meet the Experts

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Kellie Whitehead

VP of People

Jellyvision

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Senior Manager, Compensation & Benefits

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Benefits Director, Total Benefits

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Trey Griffin

Associate Manager of Benefits

HR has never been a job for the faint of heart, but lately, it feels like the pressure has been dialed up a few notches.

Costs (across the board) continue to climb. Employees expect more personalized experiences. AI is changing the way people work (and apply for jobs). And somewhere in the middle of all of that, HR teams are still expected to recruit, retain, communicate, educate, and somehow make open enrollment feel a little less overwhelming.

That’s exactly why Jellyvision recently brought together HR leaders from Hershey, Catalyst Brands, ACCO Engineered Systems, and our own VP of People, Kellie Whitehead, for a candid Poolside Chat about what it actually feels like to be leading HR right now.

While Kellie hosted the conversation, she also brought her own perspective as an HR leader navigating many of the same challenges discussed throughout the hour. 

Want to watch the full conversation? Catch the on-demand recording here.

Or, if you’re more of the reading-by-the-pool type, here are a few of our favorite moments.

People change. Great benefits evolve with them.

One of the strongest themes throughout the conversation was that employees don’t just have different benefit preferences; they have different lives. (Seems like an obvious statement, but sometimes forgotten when looking at the big picture). 

Catalyst Brands’ Dewayne Smith shared a simple story that perfectly captured why personalization matters.

I'm a 43-year-old man with a 2-year-old. When I was a 40-year-old man without a 2-year-old, my priorities and what was important to me were very different... When I think about our associates, it's how do we meet you where you are in what you need today.

A new graduate, someone welcoming their first child, an employee caring for aging parents, and someone preparing for retirement aren’t looking for the same things from their employer. Yet too often, we communicate benefits as though every offering should matter equally to everyone.

Dewayne encouraged HR leaders to think beyond individual plans and instead consider the entire rewards experience, recognizing that every employee will prioritize different pieces of it depending on where they are in life.

Kellie built on that idea while discussing benefits like expanded parental leave and gender-affirming care. She pointed out something that resonated well beyond those specific offerings: employees often appreciate working for an organization that invests in benefits they may never personally use because it reflects the kind of company they want to be part of. A benefit doesn’t have to impact every employee directly to strengthen the overall employee experience.

The conversation served as an important reminder that personalization isn’t just about technology—it’s about recognizing that people change, and the benefits they value change with them.

How ALEX Home supports personalized benefits

Employees shouldn't have to sort through dozens of benefits to figure out what's relevant to them. ALEX Home delivers personalized guidance year-round, helping employees understand the benefits that matter most based on their questions, life events, and individual needs.

Technology should create more human moments, not fewer

It wouldn’t be an HR conversation in 2026 without talking about AI.

But one of the most thoughtful moments of the discussion wasn’t about what AI can do—it was about what it shouldn’t replace.

As ACCO Engineered Systems’ Mitch Riley put it:

I've always tried to keep the human in Human Resources.

For Mitch, embracing technology doesn’t mean removing people from the equation. It means making sure employees still know when they need another human.

We have to watch what technology is doing out there... [for example], employees who are not finding success through the benefits that we have, or where AI is answering things for them incorrectly and they still need to reach a live person.

That philosophy carried through to benefits education, too.

Instead of overwhelming employees with every possible program, Mitch shared one of the day’s most memorable analogies:

If you've got a family... let us help find the answers for you, instead of dropping the Cheesecake Factory menu of options in front of you and letting them have to sift through everything.

The audience clearly connected with the analogy (and yes, defended Cheesecake Factory in the chat).

But underneath the laughs was a serious point.

Employees don’t necessarily need more information. They need to understand which information actually matters to them.

Technology is at its best when it removes complexity so HR teams have more time for the conversations that truly require empathy, context, and human judgment.

Technology should make HR more human

ALEX Home helps answer routine benefits questions, guide employees through complex decisions, and knows when it's time to direct someone back to HR—giving your team more time for the conversations that matter most.

Bridging yesterday’s expectations with today’s realities

One of the most honest conversations of the afternoon centered around something nearly every HR leader has experienced: balancing employee expectations with business realities.

For Chantrey Griffin at Hershey, that challenge is especially visible in an organization with many long-tenured employees.

She described the difficult conversations that happen when employees compare today’s benefits with those offered years ago.

Healthcare costs have changed. Business priorities have changed. What employers can sustainably offer has changed.

But employees understandably feel those changes most directly in their paycheck.

As Chantrey explained:

Premiums go up every year... It's a constant fight of them understanding, 'Why are we paying more? I feel like we're getting less.' I promise you, you're never in that boat alone.

That sentiment extended far beyond the panel.

Throughout the discussion, attendees shared similar experiences in the chat—talking about rising healthcare costs, tighter compensation budgets, shifting more costs to employees, and the challenge of helping people understand why those changes are happening. Others shared creative ways they’re recognizing employees beyond compensation and investing in wellness despite budget pressures.

It became clear that this isn’t a challenge unique to one company or one industry.

It’s the balancing act HR teams everywhere are navigating right now.

The biggest takeaway? HR leaders need each other

One of the most valuable parts of the event wasn’t actually what happened on screen.

It was what happened in the chat.

As the conversation unfolded, HR leaders began sharing ideas of their own.

One attendee described rewarding employees for completing annual physicals and celebrating healthy behaviors. Another shared details about their on-site gym and fitness reimbursement program. Others exchanged ideas around recognition programs and ways to build stronger employee engagement without relying solely on compensation.

When the conversation shifted to AI, attendees compared how they were already using it to draft policies, rewrite emails, summarize documents, and create efficiencies for their teams. 

Nobody claimed to have everything figured out.

Instead, the webinar evolved into something even better: a community of HR leaders validating one another’s experiences, swapping practical ideas, and realizing just how many of today’s challenges are shared.

One attendee summed it up perfectly before signing off:

It’s good to recognize we all are dealing with the same issues.

That’s probably the biggest takeaway from the entire conversation.

Whether you’re supporting 500 employees or 50,000, whether you’ve been in HR for two years or twenty, chances are you’ve asked many of the same questions discussed during this hour.

  • How do we personalize benefits without adding complexity?
  • How do we help employees become better healthcare consumers?
  • How do we embrace AI without losing the human touch?
  • How do we create an employee experience people value while balancing the realities every business is facing?

Those aren’t easy problems to solve.

But it’s reassuring to know you’re not the only one trying to solve them.

HR has enough on its plate.

No technology can solve healthcare inflation, erase budget constraints, or eliminate every challenge facing HR teams today. But it can make other parts of your job easier. 

ALEX Home gives employees a trusted place to get personalized benefits guidance, answers routine questions throughout the year, and helps people better understand—and confidently use—the benefits available to them. That means more time to focus on the strategic, human work that only HR leaders can do.

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