The Secret to Better Benefits Participation? Smarter Open Enrollment Tools

Open enrollment is one of those tricky events that often feel like a chore. For employees, it’s about sifting through plan documents, comparing options that all seem to blur together, and making decisions that impact their health and finances for the coming year. For HR teams, it’s about coordinating communications, answering repetitive questions, and managing a mountain of paperwork.

Now, consider this: what if this process didn’t have to be so taxing? What if technology could transform open enrollment from a stressful obligation into a streamlined, engaging experience?

Communication That Actually Connects

One of the most significant challenges during open enrollment is ensuring that employees understand their benefit options. Traditional methods — paper brochures, mass emails, and in-person meetings — often fall short thanks to being static and impersonal. Smarter open enrollment tools, on the other hand, are dynamic and interactive platforms that engage employees and facilitate two-way communication.

E.g., PRE Holding implemented an online benefits portal to streamline its open enrollment process. According to Mary Riley, the company’s payroll and benefits manager, the new system significantly reduced the number of employee inquiries about benefits. Riley says that now "employees can often find what they’re looking for online," which reduces the burden on HR.

Open enrollment tools typically feature chatbots, FAQs, and video tutorials, so everyone can choose the option that suits them best.

Remote Onboarding, Simplified

The shift towards remote work made one thing painfully clear: if your onboarding and enrollment processes depend on hallway conversations or printed guides, you’re already behind. Open enrollment software helps with remote onboarding by offering a digital-first, self-service experience that doesn’t rely on physical presence or outdated workflows.

GitLab, a fully remote company, is a perfect example. It doubled its headcount in one year by relying entirely on open enrollment tools to integrate new hires. New employees received interactive benefits walkthroughs tailored to their country, role, and family situation. The software also scheduled check-ins automatically and tracked which sections had been reviewed.

"We don’t have desks, so everything had to work asynchronously," says Head of Total Rewards Lana Brindley. "Without our platform, there’s no way we’d have onboarded that many people without chaos."

Personalization Matters

Traditional open enrollment methods often fall short in terms of engagement. Generic emails and one-size-fits-all presentations rarely resonate with everyone. Smarter open enrollment tools address this issue promptly: they offer personalized experiences that cater to individual preferences.

In other words, personalized tools guide employees through the enrollment process and automatically suggest benefit options based on their situations.

Simplifying Decision-Making

One of the most daunting aspects of open enrollment is the complexity of the decisions employees must make. Health plans, retirement options, and other benefits can be difficult to compare and understand. Smart open enrollment tools simplify this process as they provide clear, concise information and decision-support tools.

I.e., some platforms offer side-by-side comparisons of different plan options and highlight key differences in coverage, cost, and provider networks. Others include calculators that estimate additional costs based on an employee’s usage patterns.

Reducing Information Overload

The amount of information presented during open enrollment can be overwhelming. One of the most underappreciated strengths of using open enrollment software is how it limits the mental burden on employees. It organizes and displays information in so that it’s easy to digest. Instead of long PDFs buried in emails, software can break the content into bite-sized, interactive elements.

Tooltips, collapsible sections, visual plan comparisons, and filterable options aren’t just nice features anymore. They allow employees to engage with information at their own pace and in a format that suits them best.

Software That Serves HR and Employees Equally

There’s a misconception that open enrollment tools exist only to serve HR departments. To be sure, they do help them process data and stay compliant. However, this statement overlooks the bigger picture. The right platform isn’t just a backend system. Instead, it is a communication tool, a translator, and a guide for employees who are expected to make high-stakes decisions with very little help. When they feel that the tool is working for them, they engage differently.

Spotify’s People Experience team made this realization early. After struggling with low participation in their supplemental benefits programs, they shifted to using open enrollment software that included proactive prompts, usage tips, and simple videos explaining each benefit. Participation rose by 38% in the first year.

Says their senior HR manager, Leila Moshiri: "The biggest difference was that employees stopped treating enrollment like a transaction. They saw it as part of their compensation, not paperwork."

Empowering Employees to Ask Better Questions

There’s a huge difference between employees asking "What does this mean?" and "Which of these fits me better?" The first is a symptom of bad communication. The latter is a sign that someone is engaged and thinking critically about their choices. Smarter enrollment platforms encourage the latter by transforming employees into active participants in their own decision-making process. The empowerment is subtle, but powerful nevertheless.

At Canva, employees use a benefits system that gives them visual walkthroughs, estimated cost projections, and AI-driven suggestions based on previous selections. It doesn’t decide for them; rather, it gives them the data to make solid decisions.

Canva’s HR lead Chai O’Connell says: "People aren’t coming to us lost. They come with better questions. We can actually help them instead of just explaining the basics over and over."

That’s what using open enrollment software does when it’s built for clarity, not complexity.

Start Small, Grow Big

Evidently, smarter open enrollment tools don’t just simplify the enrollment process. They enhance communication, boost engagement, and support remote employees. These tools can help businesses transform open enrollment from a burdensome task into a user-friendly experience that benefits everyone.

After all, new tech is advancing at a rapid pace. Everything that’s happening now is certain to accelerate sooner than anyone may imagine. Getting people familiar with these tools sooner rather than later is a strategic decision, and one that benefits everyone involved.

Angela Ash is an expert writer, editor and marketer, with a unique voice and expert knowledge. She focuses on topics related to remote work, freelancing, entrepreneurship and more.