Open enrollment is one of the most important times of year for brokers — not just to support clients in the moment, but to build long-term trust and demonstrate strategic value beyond plan selection. Today’s employers are stretched thin, and they’re looking for strategic partners who can help reduce costs, boost employee satisfaction, and streamline the enrollment process.

Whether you support large enterprises or growing startups, these five strategies can help you stand out this open enrollment season — and strengthen relationships that last all year long.

Prioritize Personalized, Multi-Channel Communication

Employees absorb information in different ways. Some need time to review in writing. Others want live Q&A. And many rely on trusted managers to walk them through options.

Help your clients reach every type of learner by offering:

• Customizable materials for employees

• Pre-built benefits presentations or talking points

• Communication calendars or email templates

• Live or recorded webinars

• FAQs or internal landing pages

If you offer direct employee support — like chat or one-on-one consults — now’s the time to highlight it. Making benefits easier to understand reduces friction for HR and helps employees make informed choices they won’t regret later.

Make the Case for Virtual-First Enrollment

Digital enrollment isn't just convenient — it's expected. Many employees work remotely or across different time zones, and family decision-making often happens outside traditional hours.

Support your clients in creating a fully virtual enrollment experience by:

• Ensuring mobile-friendly resources

• Providing on-demand videos and guides

• Offering after-hours support

• Including dependents in the decision process

This flexibility can lead to higher engagement, fewer enrollment mistakes, and a more empowered workforce.

Bring in More Than Just HR

To build a benefits package that truly meets employee needs, brokers should go beyond HR and engage other key stakeholders. Department heads and team leads often have a pulse on what their teams are struggling with — whether it’s confusion around plan options, dissatisfaction with specific offerings, or low engagement with certain benefits.Encourage your clients to:

• Collect informal feedback from managers on common employee questions or pain points

• Involve leadership in benefits presentations to reinforce support and credibility

• Use surveys or small-group discussions to hear directly from employees — especially those who may not voice concerns to their managers

This broader engagement strategy not only surfaces more actionable insights, but also ensures benefits education feels consistent, supported, and trustworthy across the organization. When employees see leadership involved and their feedback reflected in plan decisions, they’re more likely to feel empowered and satisfied with the outcome.

Translate Benefits into Real-Life Scenarios

Plan brochures often fall short because they rely on technical language and abstract descriptions. For many employees, especially those unfamiliar with healthcare terms, this leads to confusion, indecision, or worse — defaulting to plans that aren’t the right fit. To truly support your clients, you need to help employees connect the dots between benefits options and everyday life. The goal isn’t just education — it’s empowerment through clarity and confidence.

Offer content and tools that:

• Use simple, jargon-free language to explain complex benefits

• Walk through relatable scenarios — like how an HSA can help cover unexpected ER bills after a bike accident, or how a high-deductible plan works when managing a chronic condition

• Share real employee stories or testimonials that show how others have successfully used their benefits

• Break down trade-offs visually — such as comparing monthly premiums vs. out-of-pocket costs, or highlighting plan differences in terms of family needs or provider flexibility

You’re not just presenting plan options — you’re helping employees understand how those plans show up in real moments that matter. When people can visualize the impact of their choices, they make smarter decisions, use their benefits more proactively, and feel more satisfied with what their employer offers.

Show Up with Excellent Service

Open enrollment moves quickly, and for many employees, it’s the only time all year they’ll think critically about their benefits. Questions will come fast — and the brokers who truly stand out are the ones who stay responsive, helpful, and proactive throughout the entire process. Being available when it counts can reduce confusion, minimize mistakes, and show your clients (and their employees) that they’re not navigating this alone. If your team offers any of the following, now’s the time to highlight it:

• Fast response times, especially during peak enrollment windows

• Dedicated support contacts employees can actually reach

• Real-time troubleshooting or guidance during enrollment

Even simple acts of service can make a lasting impression.

Final Thoughts

The health insurance landscape is constantly changing and it’s impossible for employers and employees alike to stay on top of it all. That’s where you shine. By using your expertise to not only help employers make good decisions, but to communicate those decisions to their employees and help employees in turn make good decisions, you can become an irreplaceable partner to your clients.

If you’re looking to refresh your HSA or FSA offerings this season and work with an open enrollment partner that’s easy to use and has great customer service, reach out to us at Lively.

Disclaimer: the content presented in this article is for informational purposes only, and is not, and must not be considered tax, investment, legal, accounting or financial planning advice, nor a recommendation as to a specific course of action. Investors should consult all available information, including fund prospectuses, and consult with appropriate tax, investment, accounting, legal, and accounting professionals, as appropriate, before making any investment or utilizing any financial planning strategy.