Employee Benefits Open Enrollment in a Virtual World

As employers navigate the new workplace structure (remote, hybrid and/or in office) many companies are considering continuing virtual open enrollment and communications. Read more to prepare now for the coming enrollment season to ensure that you reach all of your employees, at all levels, across all locations.

As employers navigate the new workplace structure (remote, hybrid, and/or in office arrangements) many companies are considering continuing virtual open enrollment and ongoing employee communications virtually. Given the evolution of the multi-location workforce, the days of conducting in-person enrollment meetings and benefits fairs may be far less commonplace in the future. Employers should prepare now for the coming enrollment season to ensure they reach all employees, at all levels, across all locations.

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Why Virtual Enrollment is Growing

In the fall of 2020, virtual enrollment became a necessary “experiment” for many employers. In 2021, it is essential. Last year, executives and workers alike learned how to use Zoom meetings, mobile apps, and digital tools. This year, employers, employees, and benefit providers have a year’s worth of experience with virtual engagement and have fewer technology hurdles to overcome with their audience.

Many employers are still formulating their return-to-office policies and timing. No matter what employers choose, they can rest assured the majority of their workforce will have the capability to access virtual enrollment tools no matter where they work. Work-from-home (WFH) employees, frontline workers, field staff, and onsite personnel can all use desktop and mobile apps to access virtual enrollment applications.

Virtual enrollment helps employers meet employees where they are: home, office, or a hybrid of both. Employee engagement has never been more critical, especially as employers struggle to attract and retain talented staff members to support our economy. Great benefits are essential to employee satisfaction, with one study indicating that 30% of employees plan to leave their current employer for other companies that offer better benefits. Choosing benefits that support employees while also communicating employer benefit program value throughout the year is a game-changer.

While virtual open enrollment tools can help enroll most employees, some employers may need to have other resources. Traditional in-person meetings, paper forms, and other enrollment tools may be needed to help the smaller percentage who do not have access or choose not to use virtual tools. Manual processes will serve those employees who do not have internet or mobile access, have language barriers, need additional information, or require personal assistance in the enrollment process.

Employees Need the Human Touch

Virtual enrollment is an efficient way to enroll employees. However, employees need more than digital platforms and reminders. Employees want to know their employer understands their challenges while ensuring they are making the right choice. Enrollment is not a black-and-white decision. Employees need their employers to be authentically human and do more than help them check a box.

Employers need to connect with employees personally and help them make the benefit choices that work for the employee’s unique needs. Companies can help their employees make the best benefit decisions by:

  • Involve the whole family. Gone are the days of only providing information to the employee. Many employees have spouses, partners, and family members who make the benefits decisions. At Woodruff Sawyer, one of the resources we offer to clients is recorded sessions that employees can view on-demand. These videos allow the employee and their household members to watch or listen to a recorded open enrollment presentation at a time that is convenient for them.
  • Provide multilingual, diverse communications. Employers must reach a broad spectrum of diverse employees, communicating with them in a way they will understand. Providing information in their language of choice, on the device of their choice, supports an inclusive culture that engages all employees.
  • Promote benefits throughout the year. Employee benefits are a rich suite of offerings that include health and wellness, mental health, vision and dental, and consumer-directed benefits like FSA, HSA, and DCAP. Year-round and mid-year program reminders are a great way to stay connected with employees by telling them how to access these benefits before they need them.
  • Publish frequent, small sound bites. Over the last year, many people have felt overwhelmed by constant news updates and challenges. When our brains are at capacity, they are likely to fail to process some information. The brain can only absorb so much information at once, so taking the time to communicate in snippets throughout the year will support your employee engagement strategy. Create smaller communication bits that support employees’ knowledge of benefits beyond open enrollment, including emails, texts, and virtual events throughout the year to remind them of their benefit offerings.

We often hear that employees are confused, worried, or stressed about their benefits. These annual decisions can impact an employee’s overall wellbeing, including their health, wealth, and emotional well-being. Creating the approximate mix and delivery of communication materials to meet employees where they are in the way they want to receive information will ensure you have the right employee engagement strategy for 2021 and beyond.

The key to a successful virtual enrollment is preparation. Employers will need to work with their consultant or broker to have a strategy in place, understand potential employee concerns, prepare a thorough communication plan, and update enrollment platforms. The benefit of this approach is that the time put into planning will make it easier to execute enrollment and reach employees. Here’s an overview of what it takes to prepare for virtual enrollment as well as a checklist that may be helpful as you map out plans for your upcoming renewal season.

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8–12 Weeks Before Open Enrollment

Once benefit decisions are made, HR (with the help of their consultant) will set up enrollment platforms, update employee information, upload plan information, prepare educational materials, create communication plans, and perform other enrollment tasks. If possible, we suggest a passive open enrollment (where employee elections only need to be made if making changes) if only minor plan or benefit changes are being made. Experts recommend working on these tasks 8–12 weeks before the open enrollment event to ensure all information is up to date. Note this timeline may need to be tweaked depending on when carrier renewal information is available.

8–12 Weeks Before Open Enrollment
Maintain records of employee questions, comments, and concerns.
Survey employees on what they are seeking for offerings or improvements.
Identify enrollment needs to introduce or revamp. Make note of what’s new and exciting so it can be highlighted later with employees.
Begin developing the benefits guide.
Consider online enrollment programs and software.
Develop online educational materials such as FAQs, videos, calculators, and downloadable documents or forms.

1–4 Weeks Before Open Enrollment

Promote virtual enrollment by publishing and distributing content that demonstrates the value of the employee benefits program. Employers should make sure managers and employees are well-informed to make important benefits decisions. During this time, benefits administration staff will distribute webinar event invites, brochures, and detailed information that employees need to make their benefit choices. For employees who cannot participate in virtual open enrollment, share alternative ways to receive information and enroll in benefits programs

4 Weeks Before Open Enrollment
Begin publishing enrollment content, using online enrollment programs and software.
Develop a toolkit for managers (including talking points and FAQs).
Add an open enrollment reminder to the email signatures of management.
1–2 Weeks Before Open Enrollment
Host virtual benefits meetings, webinar events, and one-on-one meetings, as needed.
Send pamphlets, brochures, or other mailers to employees.
Anticipate FAQs, and craft succinct answers.

Conduct Open Enrollment

Engaging employees, answering questions, and signing employees up for benefits happen in a short time. Send out positive and encouraging reminders that make enrollment a satisfying and positive experience. Ensure that managers and/or your HR call center understand benefit offerings as they will often be the first contacts that employees reach out to for benefits advice. Provide incentives to employees through raffles or gift cards to encourage their participation in virtual open enrollment meetings.

During Open Enrollment

Make sure employees receive all of the following materials:

  • Open enrollment schedule
  • Statement of current coverage
  • Plan-specific changes and rates
  • Plan-specific summaries
  • Open enrollment booklet and forms
  • Deadline for open enrollment
  • Carrier contact information
Remind managers to talk with their teams.
Offer generous deadlines, with frequent reminders.
Remain available through various mediums for employees to contact with questions and clarification.
Schedule a companywide reminder for the day before the enrollment deadline.


Immediately after open enrollment, staff will answer outstanding questions, ensure all employees are signed up, and the employers submit data to carriers. However, benefits education and awareness is a year-round activity that helps everyone get the most from the employer’s benefit investment.

It’s Almost Time for Open Enrollment

Open enrollment will be here before you know. Employers should work with their consultant to prepare for open enrollment season by evaluating their current suite of benefits while envisioning what they will need in 2022.

Employee surveys are a great way to tap into what your workforce needs now as they return to work. After gathering those insights, employers have a better idea of benefits that will keep current employees engaged while attracting new talent, setting the groundwork for virtual open enrollment.

Woodruff Sawyer’s benefits consultants have the expertise to align your benefit offerings, budget, and employees while adding the human touch to ensure those benefits get used throughout the year.

Preparing for an Unprecedented Open Enrollment Period


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