Open Enrollment: Considerations for Success

August 11, 2026
Open Enrollment: Considerations for Success

Don’t worry, it’s not quite that time of year yet. It seems to happen every year, though – before we know it, it’s open enrollment. So, this year, to ensure it doesn’t sneak up on HR benefit leaders like you, we want to give you some advice early to ensure you have a successful open enrollment period.

These four considerations, and the elements to think about within them, will broadly put you in a place where open enrollment will run smoothly, even while keeping in mind that exact processes should be specific to your organization’s needs.

It sounds obvious, but preparing for open enrollment as early as possible is key. It seems to come up quicker every year, and it really can sneak up on your team if you don’t prepare well ahead of time.

It’s important to consider company priorities and decisions as early as you can – ideally, 2-3 months before you finalize plans for the upcoming benefit plan year. Determine how much time and bandwidth you have to support open enrollment and start conversations with a broker as early as possible if you’re working with one.

If your vendors, plans, options, or rates are changing, engage with your vendor or implementation partner (like an HRchitect) as early as possible. If working with an implementation partner, you should try to engage with them before your vendors, plans, options, and rates are finalized.

We recommend signing a support contract early so you ensure you have a consultant lined up to start with you once benefit plans are finalized. Open enrollment is a time with extremely high demand for support from an implementation partner, as many organizations look for help. You don’t want to be at the back of the line for assistance when it’s needed.

Determine if you need new or updated integrations or file feeds, or if data transfer will be manual for any changes. If you need new or updated integrations, request copies of specification documents from you’re the technical team at your benefit vendor(s) as early as possible. If you’re working with an implementation partner, they will need these specification documents, whether creating a new integration or updating an existing one.  Because of this, you should connect your vendor with your implementation partner as soon as possible.

Your internal team will have expertise that you need to harness. Figure out how much bandwidth your team has and the level of internal system knowledge, then assign them appropriately to tasks where they can be considered a subject matter expert.

If knowledge is low, revisit benefits configurations and/or open enrollment training before the project begins so the team has the knowledge needed.

Roles you need to determine include:

  • A project manager to own tasks and milestones throughout the process to ensure timelines are met.
    • This person will likely need to be comfortable managing a project involving internal and external resources.
  • Testing resources and field users.
  • Decision makers who will be available throughout critical milestones can sign off on decision points, next steps, and go-live.
  • An owner of the employee rollout plan who determines details such as location, timing, method, documentation, and support contacts.
    • This person should be a proactive communicator who will be able to inform employees of upcoming dates early and let them know there’s more important information to come.
    • If this is a person or skill set your team doesn’t have, implementation partners, such as HRchitect, offer change management services for open enrollment rollouts.

Many times, organizations look for a third-party implementer, like an HRchitect, for help. Depending on scope, we typically assist with things like project management, configuration updates, and new and modified integrations and file feeds. The type of third-party implementer you work with should be based on their capabilities, where the holes in your internal expertise and experience lie, and where you’re lacking bandwidth.

You should meet with your implementer regularly (we generally recommend weekly) and ensure there is mutual understanding of milestone ownership and timelines. Block out time for working sessions internally and with your implementer for tasks like discovery, configuration reviews, and internal testing sessions. Collect testing feedback in one place, like Excel, Google Sheets, or Smartsheet, to centralize information, status, and resolutions.

Ensure you are aligned on processes for go-live, and, when the time comes, that functionality is working as expected before something goes live from either side. If you anticipate needing support with open enrollment or benefits beyond the initial rollout, ensure your implementer is capable of that and that you have mentioned these extra areas where support will be needed as early as possible. Things they may help with include issue resolution and integration/file feed go-live and support activities.

The employee rollout plan is crucial because, regardless of how well everything is set up behind the scenes, it needs to go well for open enrollment to be seen as a success.

HR teams also need to take into account that while they know open enrollment is important, employees sometimes tune out corporate emails, and they may just treat open enrollment as white noise. This means your rollout plan is vital to ensure it cuts through the noise and employees know they need to act.

Before rolling out to employees, you need to:

  • Double-check that system access is granted to everyone, links to plan documents are working, and that the open enrollment workflow is functioning as expected through testing.
  • Determine who will field questions from employees as they arise during open enrollment. Ensure there is appropriate coverage here because these will come in waves early in the period and at the end of it.
  • Plan out communications ahead of time to ensure employees understand how to log in, timing, due dates, and any potential loss of benefits if they’re not acted upon.
    • Consider reminders throughout the open enrollment period to prompt late adopters to complete their tasks.

You should also ensure insurance cards go out on time if they’re needed by working to understand timing from the benefit vendor and ensuring the required data is sent to the vendor by the deadline. Once you know when they’re expected to be sent out, you should inform employees of what to expect and when they’ll receive their new cards.

As we mentioned earlier, it’s not open enrollment time yet, but it’s important to be prepared. Plan out what you need and reach out to those that you need to work with early. If you need help planning your rollout, these activities are still a good way to make your open enrollment stand out. And if you need help with anything detailed in this piece, we would love to hear from you.

Kasey Dempsey

Kasey is a Service Excellence Manager and Certified Project Manager PMP at HRchitect who helps teams and clients move from “we have a goal” to “we got there,” with the structure, support and follow-through that keeps work on track and outcomes strong.

Kasey is passionate about building new processes and improving existing ones to create efficiency wherever possible. On the support side of the business she and teammates are consistently relied upon to stay agile and adjust quickly when client needs shift.

Learn more about Kasey on LinkedIn.