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How to run a successful virtual open enrollment

Small Business • May 27, 2022 at 8:30 AM • Written by: Elizabeth Walker

With more companies going fully remote and a growing demand from employees for more flexible work schedules, it’s a critical time for HR professionals to adapt to the new environment and adjust their benefits enrollment strategy.

If most or all of your employees are working from home, your usual, in-person benefits fair may no longer be an option when open enrollment comes around. Say goodbye to formal benefits presentations, print materials, and an extensive agenda—it’s time for virtual open enrollment!

Open enrollment is the time of the year for your workforce to choose their employee benefits, such as healthcare, dental and vision, and life insurance. Virtual enrollment can be exciting because it’s less formal and more flexible. But for some HR teams, it means exploring new and unfamiliar territory of virtual benefit offerings, which can be daunting.

If you’re ready to make the switch but you’re unsure how to go about it, we’ve got the HR tips and tricks you need to offer your first virtual open enrollment without a hitch.

Download our full HR handbook to running a virtual open enrollment at your organization

How does open enrollment work?

Under the Affordable Care Act (ACA), open enrollment is the dedicated period for employees to enroll, renew, or change their health coverage. Typically, this enrollment period applies to your company's health, dental, vision, life, and disability insurance plans.

Open enrollment is a great time to start thinking about your employer-sponsored benefits to ensure you’re offering the best perks to help recruit and retain top talent. Hence, it’s important for benefits specialists to carefully consider benefits programs and options.

Having open enrollment as the only time employees can change their coverage ensures they don’t wait until they get sick to enroll in coverage, or switch to a more comprehensive plan when they’re about to have an expensive medical procedure.

While the exact dates vary depending on your state, the open enrollment period generally starts at the beginning of November and ends in mid-December. However, some states extend their enrollment deadline to January or February.

Virtual open enrollment is new for many HR professionals. Let’s go over four key steps below to help you implement one for your company.

Check out your state’s open enrollment details in our state-by-state guide

Step 1: Planning for a virtual open enrollment

The first step in planning your virtual enrollment event is choosing your administration method. Using an employee benefits administration tool can help you eliminate benefits confusion, drive smarter enrollment decision-making, and reduce healthcare costs for your employees and your company.

There are typically two ways to administer virtual open enrollment:

  1. Building your own virtual system, or
  2. Selecting an HR platform that offers virtual enrollment

These benefit administration tools for virtual open enrollment help employers select and administer benefits packages for their organization. They also provide employee information about plan types, compare plans, automate the enrollment or re-enrollment process, and manage compliance regulations.

Building your own system means putting more money down initially, but you have the option for greater customization. Remember, you’ll still need to follow all ACA compliance regulations on offering health insurance benefits, so you may want to work with a broker to avoid penalties if you choose to go this route.

An off-the-shelf platform requires less financial investment, so it’s the option that makes many small businesses feel more comfortable. Plus, there are usually guarantees or support for any non-compliance from these HR enrollment platforms to better mitigate your risk.

Lastly, if your organization is only making minor changes to your benefits offerings, you can designate the virtual open enrollment period as passive. This allows your employees’ elections to roll over automatically into the new plan year. But keep in mind that some benefits, like flexible spending accounts (FSAs), require re-enrollment each year, so rollovers aren’t allowed.

Step 2: Selecting the employee benefits you want to offer

Even though open enrollment only applies to health insurance, it’s a good time for benefit specialists to assess their other employee benefit options. If this is the first time you’re doing virtual open enrollment meetings, it’s more important than ever to find out what benefits your employees value the most. An effective route to go about doing this is by surveying your employees.

Asking your employees for feedback on your benefits plan will help you understand what matters most to them. Based on survey results, you can better understand how they feel about your current benefit offerings and what new benefits you should investigate adding to your compensation package.

There are traditional employee benefits that most industry experts say job seekers expect to see. And then there are specialty benefits perks that help employers stand out.

Below are four popular benefit choices you can consider for your company:

  • Healthcare: Consider all health benefit options like employer-sponsored health insurance, health reimbursement arrangements (HRAs), employee stipends, and health savings accounts (HSAs).
  • Paid time off and paid family leave: Companies that provide paid time off and family leave have an edge during hiring. It’s a perk that allows employees to recharge, so they’re better focused on their work.
  • Flexible hours: The COVID-19 pandemic has made flexibility more important than ever before. Flexible work hours help employees with young children or elderly parents maintain a good work-life balance.
  • Wellness perks: Many employees value their fitness and mental health, and employers benefit from a healthy, active workforce.

Employee benefits are vital to attracting and retaining top talent for your workforce. However, finding the right mix of benefits to succeed is a challenge. It’s never wise to select benefits that your employees don’t want or won’t use. You should ask them the types of benefits they genuinely value and then shop for a benefits provider or that offers cost-effective ways to provide them.

Ready to survey your employees about benefit options? Download our survey template!

Step 3: Communicating virtual open enrollment to your employees

A successful virtual open enrollment only goes so far if you fail to develop a strong communications strategy about the event. Luckily, educating your employees about your benefits can be easily done in a virtual environment, using methods like online correspondence, downloadable documents, and other educational materials.

Email campaigns are a great place to start. But remember to keep your emails brief, so it’s more likely your employees will read all its content. You can also choose to create a one-page PDF cheat sheet to highlight helpful resources and provide employees with helpful tips while they’re enrolling.

A more detailed annual benefits guide is also a great option. If you’ve done physical print material versions in the past, you simply need to convert it into a digital asset.

Other than email, the following two communication options are other tech-savvy ways to advertise open enrollment and benefits updates:

  • Text: With text open rates averaging 98% vs. 20% for email, texting can be a more effective way to contact employees and increase employee engagement.
  • Chat: Create a communication channel on your company messaging system, like Slack or Microsoft Teams, where employee questions can be answered by your HR team.

Step 4: Provide a benefits webinar or virtual office hours

If you previously kicked off your past open enrollment periods with an in-person benefits presentation, you can modify this for your remote employees by hosting info sessions as virtual events, like through Zoom meetings or Google Meet. Virtual fairs can take place in different forms, such as webinars or office hours.

A virtual benefits webinar is a handy way for HR teams to discuss enrollment basics, deadlines, and new benefits choices. Encourage your employees to attend so they can make better benefits decisions during open enrollment. Don’t forget to record the session so that employees can review it later or if your busy employees can’t attend.

Virtual office hours are an excellent substitute for the personal touch of in-person interactions with employees during HR office hours you’d usually have during open enrollment. Notify employees to sign up for pre-determined office hour time slots on your calendar.

One-on-one office hours allow employees to engage in a personalized learning experience about their benefits. They can ask a question they didn’t want to ask publicly or find out more information about benefit questions related to their specific needs.

Whether you decide on a webinar, office hours, or both, always ask for feedback and leave time for Q&A. If you have significant changes to your benefits package, you should consider hosting vendor breakout sessions for employees. For example, if you decide to offer mental health counseling, host a separate discussion to explain how individual benefit offerings work.

How PeopleKeep can help with your employee benefits

Choosing which benefits you want to offer during open enrollment doesn’t have to be scary. Many benefit solution platforms can help you provide comprehensive employee benefits without the hassle. One way to ensure that your benefits are compliant is to use a benefits administration software such as PeopleKeep.

PeopleKeep offers much more than just a user-friendly interface. With our HRA and WorkPerks employee stipend platforms, you can offer HRAs or stipends to your employees with ease. Our software solution allows businesses to simplify how they sign up, design, and administer their personalized benefits.

Our award-winning customer support team and user-friendly software will help you keep your employees informed by sending them automated communications, in-app messages, and hosting live chat sessions. We even have the support you need to keep you updated on regulations to ensure your benefit remains in compliance.

Whether you choose one of our three HRA options or an employee stipend through WorkPerks, PeopleKeep makes it easy for HR professionals to offer their employees a flexible health benefit that’s just right for them.

See what PeopleKeep is all about by watching our product demo videos


Workplaces have changed dramatically in the last few years. As an HR team, how you handle enrollment season should change too. With virtual open enrollment, HR teams can engage their employees entirely online, reducing their workload and streamlining their benefits while maintaining a thoughtful enrollment experience.

Virtual open enrollment is a great time to introduce new and exciting benefits. With PeopleKeep, our HRA and WorkPerks software platforms make offering a personalized health benefit or employee stipend simple by taking care of administrative difficulties and managing compliance issues on your behalf. Schedule a call with our benefits advisors, and we’ll get you started!

Ready to enhance your employee benefits with PeopleKeep?

Elizabeth Walker

Elizabeth Walker is a content marketing specialist at PeopleKeep. She has worked for the company since April 2021. Elizabeth has been a writer for more than 20 years and has written several poems and short stories, in addition to publishing two children’s books in 2019 and 2021. Her background as a musician and love of the arts continues to inspire her writing and strengthens her ability to be creative.