The Open Enrollment Dream Team: Who to Draft and What Skills to Line Up

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Open enrollment has all the pressure of a big game—tight timelines, high expectations and no margin for error. Success depends on more than just systems; it takes a coordinated team of professionals who are prepared, responsive and ready to deliver. When HR, administrative and customer support teams step up with focus and collaboration, they turn a high-pressure moment into a winning performance for the entire organization.

Enter the open enrollment dream team. These MVPs can help ensure every deadline is met, every question gets answered and every employee walks away with benefits choices they understand and trust. Below, we highlight four of these pros and explain why their skills are so valuable to open enrollment season success.

The Open Enrollment Dream Team: Who to Draft and What Skills to Line Up

Benefits navigators: Knowledgeable guides through complexity
Administrative support: The operational backbone
Communications pros: The voice of the open enrollment campaign
Project manager: The strategic coordinator
How do you build a dream team for open enrollment—fast?
What five factors help make an open enrollment dream team successful?

Benefits navigators: Knowledgeable guides through complexity

Every dream team needs playmakers—powerhouses who move the ball forward, set the pace and make sure everyone knows the next move. In open enrollment season, these are your benefits navigators.

What is the purpose of a benefits navigator?

Benefits navigators support employees through benefits enrollment, helping them compare plans, understand out-of-pocket costs and choose the options that fit their needs. They simplify technical or confusing language, walk employees through “what’s changing” scenarios, and escalate complex cases to the right partner so no one gets stuck on the sidelines.

Skills to look for:

Deep knowledge of benefits offerings

Empathetic coaching style

Clear, jargon-free communication

Fluency with your enrollment platform or human resources information system (HRIS)

A smaller company may only need one benefits navigator, while larger organizations often rely on several—sometimes a mix of internal human resources (HR) staff and external consultants or vendor representatives. What is most important is making sure all employees in your company have a trusted guide to turn to, whether that’s a single point person or a deep bench of benefits navigators.

Administrative support: The operational backbone

On your open enrollment dream team, administrative support staff are the steady players who make sure the fundamentals are executed flawlessly.

What do administrative support professionals do during open enrollment season?

These pros handle the logistics—entering data, tracking deadlines, coordinating with vendors and making sure every form and file is accurate. They may not take the spotlight often, but their precision and consistency are what keep open enrollment season on track and running smoothly.

Skills to look for:

Strong organizational and time management skills

Attention to detail under pressure

Proficiency with HR systems and spreadsheets

Ability to juggle multiple tasks

Think of administrative support as the teammate who makes the assist—setting up others to score. Their behind-the-scenes work helps ensure HR leaders can center on strategy, benefits navigators can focus on guiding employees and staff can trust that their final choices will be processed smoothly.

Learn about the latest hiring trends for administrative support professionals.

Communications pros: The voice of the open enrollment campaign

Even the most surefire game plan will fail if no one understands what to do, when to do it and how. That’s where communications professionals step in.

What do communications professionals do during open enrollment season?

They’re the voice of your open enrollment communication strategy, crafting messages that cut through the noise and motivate employees to act. From emails and intranet posts to FAQs and visuals, they translate complex information about workplace benefits options and critical deadlines into clear, engaging content. In short, they make sure the playbook reaches all the players.

This is also where employee benefits communication makes or breaks the season. Clear, timely updates help employees feel supported, reduce confusion and drive more robust participation in the open enrollment process.

Skills to look for:

Strong writing and editing abilities

Visual storytelling and design skills

Knowledge of employee engagement strategies

Comfort with internal communication tools and platforms

With skilled communicators on your dream team, an open enrollment communication strategy feels less like a flood of fine print and deadline alerts, and more like a guided journey.

Get tips on managing benefits enrollment for a multigenerational workforce.

Project manager: The strategic coordinator

Every team needs a confident leader who can see the whole court, call the plays and keep everyone moving in sync. In open enrollment season, that’s your project manager.

What does a project manager do during open enrollment?

They oversee the timeline, align stakeholders, manage deliverables and make sure nothing slips through the cracks. Whether they’re called a project manager, project lead or team lead, this role is the captain of your open enrollment dream team.

When deadlines loom and details pile up, the project manager is the calm center. They anticipate roadblocks, rally cross-functional teams and keep the campaign on track from tipoff to the final buzzer.

Skills to look for:

Project planning and execution expertise

Cross-team coordination and communication

Risk management and problem-solving ability

Knowledge of benefits compliance and deadlines

With a strong project manager or project lead at the helm, your dream team can execute a smooth open enrollment process—one where employees feel supported and HR can breathe easy.

How do you build a dream team for open enrollment—fast?

After you’ve mapped out essential roles, including benefits navigator, administrative support, communications pro, and project manager or project lead, take a hard look at your internal roster. Where do you already have strong players? Where are the gaps?

Some HR teams can cross-train staff to step in as benefits guides or communications partners. Others may need to scale quickly with contract professionals who can hit the ground running.

A flexible staffing strategy can provide a strong advantage during open enrollment. By blending permanent staff with interim support, you can right-size your team to the workload—building capacity for the peak open enrollment season without overextending your core resources.

What five factors help make an open enrollment dream team successful?

Building a strong lineup is just the start. The most effective dream teams share five traits that keep the open enrollment process on track:

1. Clear roles and responsibilities—Every player knows their position and assignments, what success looks like, and how it is measured.

2. Strong communication—A coordinated open enrollment communication strategy helps ensure employees across the organization receive consistent, timely messages that resonate.

3. Flexibility—Dream teams can adapt to unexpected changes in vendors, systems or employee needs without losing momentum.

4. Employee focus—Every decision is centered on making benefits enrollment clear, accessible and as stress-free as possible for all employees, including remote staff.

5. Leadership and coordination—Whether they have a project manager, project lead or team lead at the helm, the whole team stays aligned, works collaboratively and calls the right plays.

When these five elements come together, the annual open enrollment season can run smoothly, and employees can walk away confident in their benefits choices.

Winning the open enrollment season—with help from Robert Half

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Open enrollment season doesn’t have to feel like a constant scramble. With the right lineup—benefits navigators guiding employees through benefits enrollment, administrative support staff handling the fine details, communication pros driving clear messaging, and a project manager steering the process, you’ve got a dream team built to win.

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