With a recent Gallup report finding that only 21% of employees are engaged at work, connecting with your remote workforce has never been more critical. As an HR leader or benefits broker, you know the old open enrollment playbook of in-person fairs and breakroom posters is no longer effective. It’s time to reimagine your approach.

For remote and hybrid employees, open enrollment is your single most important annual touchpoint to reinforce company culture and demonstrate care. In this article, we’ll go beyond a simple checklist into a playbook of modern HR strategies designed to help you create a successful and engaging enrollment experience.

Treat Open Enrollment as an Annual Experience

For years, you have likely treated open enrollment as a necessary process to be managed with timelines and checklists. For a hybrid workforce, this administrative mindset is no longer enough. To truly connect with employees who feel disconnected, you must stop managing a process and start designing an experience.

Think of yourself as a product manager. The “product” is the journey employees take to make their benefits decisions, and the “users” are a distributed team with limited time and attention. Like any good product, this journey needs to be intuitive, engaging, and solve their underlying problems.

This shift in thinking moves you from simply broadcasting information to actively guiding employees. It starts with mapping the employee’s user journey to anticipate their questions and anxieties. You conduct “friction audits” to find and eliminate every confusing login and every 50-page PDF that might cause a remote employee to give up.

When you design the open enrollment experience, you transform it from a yearly chore into a clear demonstration of your company’s value.

1. Create Clarity and Cure “Benefits Blindness”

The modern benefits package is a powerful tool, but its very richness can be its downfall. You offer multiple medical plans, dental options, an FSA, an HSA, and a suite of voluntary benefits. For an employee making these complex financial decisions alone at their kitchen table, this can lead to “choice overload,” a state of anxiety that usually results in poor decisions.

An Aflac report confirmed this, finding that a staggering 48% of employees do not fully understand their benefits package. This “benefits blindness” means your significant investment in employee well-being is not having its intended impact.

A Strategy for Clearer Employee Benefits Communication

The goal is to move from being a provider of information to a facilitator of decisions. Instead of simply sending dense plan comparison charts, build interactive decision-support tools. These can be simple online calculators that help an employee estimate their costs or tools that recommend a plan based on their answers to a few key questions.

A highly effective tactic is to create curated “benefit bundles” for different employee personas. You might design a “New Professional” bundle that suggests a high-deductible plan paired with an HSA. A ‘Growing Family’ bundle, on the other hand, could highlight your best PPO plan, the dependent care FSA, and family-focused voluntary benefits that cover everyone, from kids to pets.

By curating the options, you simplify the choice and make the value of your offerings immediately clear.

2. Foster a Human Connection with Hybrid Employees

Remote employees are drowning in a sea of digital noise. Their days are filled with endless emails, constant chat notifications, and back-to-back video calls. Critical open enrollment communications compete for attention with every other project deadline, a battle you can’t win with a single, long-winded email.

A “Micro-Communication” Strategy Across Multiple Channels

To cut through the noise, break down information into bite-sized, easily digestible pieces and deliver them across multiple channels. This is a “micro-communication” strategy.

Instead of one massive benefits guide, create a series of short, engaging videos explaining each core benefit, post quick-reference guides on the company intranet, and use scheduled reminders in Slack or Microsoft Teams.

This approach respects employees’ time and attention, delivering the right information in the right format, at the right moment.

Empowering Managers as “Benefits Ambassadors”

Managers are the most trusted point of contact for their teams, yet they are often left out of the enrollment process. The key is to empower them not as technical benefits experts, but as empathetic Benefits Ambassadors.

Provide them with a simple toolkit: a one-page summary of what’s new, key dates, and who to contact for specific questions. Train them to start conversations by asking, “As we head into open enrollment, what’s most important for you and your family this year?”

Their role isn’t to explain deductibles, but to reinforce the value of the benefits program and guide their team members to the right HR resources.

3. Showcase the Value of Your Full Employee Benefits Package

For an employee who rarely sets foot in an office, company culture can feel abstract. For them, your benefits package is the single most tangible and powerful proof that you care about their well-being.

A standard, impersonal package suggests a transactional relationship, while a holistic, modern package demonstrates a genuine commitment to them as a whole person.

For Remote Employees, Benefits Are Your Loudest Cultural Statement

Open enrollment is the prime opportunity to tell this story. Your communication plan should go far beyond just medical and dental. Create specific, engaging content that spotlights the full suite of voluntary benefits you offer.

Create a short video highlighting mental health resources or send a dedicated email explaining how financial wellness tools can help. Showcase in-demand perks like pet benefits that support their whole family – including the furry members – being sure to highlight plans that offer immediate discounts alongside traditional pet insurance options.

A study by Willis Towers Watson found that over 70% of employees are more likely to work for a company that offers a wide variety of these kinds of supportive benefits.

Turn a Chore into an Engaging Event with Gamification

Finally, you can combat the sterile nature of a digital process by transforming it into a fun, interactive event. A simple gamification strategy can dramatically increase engagement and build a sense of community.

Create a “Benefits Bingo” card where employees get credit for watching a video or attending a virtual session. Offer a small reward for the first 100 employees who complete their enrollment. This simple shift turns a dry administrative task into a shared, positive experience that reinforces a positive company culture for remote workers.

Putting Open Enrollment Strategies into Action

A successful open enrollment for hybrid and remote workers is about designing an experience built on clarity, connection, and care. It transforms a yearly administrative process into a powerful opportunity to build trust and company loyalty.

At Pet Benefit Solutions, we specialize in providing high-value voluntary benefits that help companies demonstrate a true culture of care. This means providing affordable options that support every member of their family – even their pets. To learn more about how we can enhance your employee benefits package, explore our plans today.