Despite decades of innovation in the workplace, from cloud computing to flexible working to AI, the way organizations manage employee benefits has barely evolved. Benefits administration still often feels clunky, confusing, and stuck in the past. Why?

In a world where nearly everything has been digitized, automated, or personalized, benefit management remains one of the most manual and least loved parts of HR. And that’s not just frustrating, it’s holding organizations back from delivering real value to their people.

So, what’s stopping change?

1. Legacy systems and siloed platforms

One of the biggest culprits is legacy infrastructure. Many HR teams are still dealing with outdated benefits platforms that can’t integrate well with newer systems. They were designed decades ago with compliance in mind—not user experience.

As a result, administering benefits is often spread across multiple systems and vendors. It’s hard to get a complete view of what's working and what isn’t. And when systems don’t talk to each other, you can’t track engagement, costs, or trends in any meaningful way.

2. Benefits built for the business, not the employee

Traditionally, benefits have been built around what the employer needs: attracting talent, meeting legal obligations, and ticking boxes during onboarding. But very little has been designed from the employee’s point of view.

The result? A maze of benefits that people either don’t understand or don’t use. Employees often have no idea what they’re entitled to, how to access it, or how it fits into their life stage. And if they don’t see the value, they won’t engage, no matter how much a company spends.

3. Fear of change

HR teams are often under-resourced and overstretched. Changing the benefits infrastructure feels risky, time-consuming, and expensive. It’s no wonder so many teams stick with what they know, even if it’s not ideal.

On top of that, benefits often sit at the intersection of HR, finance, procurement, and legal, making any change a complicated, multi-stakeholder process. With so many cooks in the kitchen, even small changes can feel impossible.

4. Lack of real-time data and insight

Most organizations can’t answer a simple question: Are our benefits working? That’s because most benefit data is historical, fragmented, or doesn’t exist at all.

Without insights into engagement, usage, cost trends, or employee sentiment, there’s no way to make strategic decisions or measure ROI. Benefits become a black box—something you offer, but don’t really manage.

What’s the opportunity?

It doesn’t have to stay this way. AI, automation, and modern data tools are opening up huge opportunities to rethink how benefits are managed and experienced.

Imagine a world where HR teams have:

• Visibility on the kind benefits they offer, where they are in the world and what they cost
• The ability to stay compliant with local regulations
• Centralized documents, all accessible in one language

This isn’t a pipe dream, it’s happening now. But it takes bold thinking, modern tech, and a shift in mindset: from benefits as a back-office function to benefits as a core part of the employee experience.

The bottom line

Benefit management hasn’t changed in 25 years because the systems, structures, and mindsets haven’t either. But the pressure is building. Employees expect more, and businesses can’t afford to waste money on benefits people don’t value.

The good news? The tools finally exist to change all that. Now it’s just a question of whether organizations are ready to step forward.