Open enrollment (OE) is one of the most important periods of the year for HR teams. Whether you're part of a large organization or managing benefits solo, the work comes down to preparation. A smooth open enrollment starts months in advance, and the steps you take early shape how confident and supported employees feel when it's time to choose their benefits.

This timeline splits open enrollment into three phases: prep, process, and post-enrollment. Each phase lists what to do and when, including the HSA steps for employers offering a high-deductible plan. For the 2027 dates, deadlines, and an employee checklist, see Lively's open enrollment guide.

Prep phase: what to do before open enrollment starts

Think of this phase as your foundation. The more organized you are early on, the fewer fire drills you'll face later. From collecting data to finalizing benefits and communicating early, the work here sets the tone for everything that follows.

60+ days before: get organized and gather information

At this stage, your main goal is to collect the internal data and paperwork your broker or benefits platform needs to provide plan quotes and funding options. You're laying the groundwork so decisions can move forward without delays.

• Confirm key open enrollment dates, deadlines, and broker and carrier timelines

• Gather current employee demographic and dependent data

• Ask your broker what documentation they need to run market quotes

• If you use alternate funding strategies, ask whether medical questionnaires are required for the coming plan year

• Coordinate with Finance or Operations on budget guardrails and cost modeling

• If you offer an HSA-eligible plan, confirm its deductible and out-of-pocket maximum still meet the IRS thresholds for 2027.

Getting this information early prevents bottlenecks when it's time to finalize benefits, and it gives you more time to review quotes and options with a clear head.

45 to 30 days before: finalize plans and draft your communication strategy

Once you've reviewed plan options and funding levels with your broker, it's time to lock things in. Then shift your focus to the messaging and materials employees will receive. This stage involves the most stakeholders, so front-load the planning work now.

• Choose final plans, contribution strategies, and any new benefits

• Set the employer HSA contribution for the year, including the amount and when deposits will land

• Draft and review OE communications for tone, clarity, and compliance

• Create a high-level communications calendar (emails, town halls, reminders)

• Pull or request updated SBCs, plan summaries, and FAQs from your broker or carriers

• Loop in legal or compliance reviewers early if needed

The sooner your messages and materials are mapped out, the more time you'll have for feedback and adjustments. It also leaves room to respond if new questions or plan changes come up.

30 days before: launch the first wave of employee communication

Employee communication should start early and go beyond a single email. Your goal now is to raise awareness, build trust, and explain what employees need to do and by when.

• Send a kickoff message announcing OE dates and high-level changes

• Invite employees to Q&A sessions, benefit fairs, or webinars

• Highlight new plans or perks that may generate questions

• Explain what happens if an employee takes no action

• Post information everywhere employees check: email, Slack, intranet, and text reminders

This first touchpoint doesn't need to answer everything. It needs to be visible, clear, and reassuring, so employees know support is coming and have a reason to pay attention.

15 to 7 days before: send final packets and prep internal teams

As open enrollment nears, shift into execution mode. Make sure employees have what they need to make confident decisions, and that your internal team knows how to handle questions, submissions, and tech issues.

• Distribute final OE packets (digital or print) with plan overviews, costs, and comparison information

• Show the full-year cost of each plan side by side, with the employer HSA contribution listed as a dollar amount on the high-deductible plan

• Include a checklist of what each employee needs to submit, and when

• Add affirmation forms for employees staying on the same plan

• Brief team members on FAQs and escalation paths

• Test online enrollment platforms to catch login or usability issues

Equipping employees and internal teams now saves hours of troubleshooting during the enrollment window.

Process phase: during open enrollment

You've done the prep. Now it's time to launch. This phase is about supporting employees as they make choices and staying organized so no one falls through the cracks.

Week 1: monitor, support, and answer questions

Expect questions and last-minute realizations. Your job now is to keep information flowing and make sure every employee knows how to get help.

• Monitor email or help desk channels for incoming questions

• Offer office hours or live Q&A sessions, with broker support if possible

• Track participation to see who hasn't started yet

• Confirm online tools and forms are capturing data correctly

• Encourage employees to submit elections early, especially if they're switching plans

• Point HSA eligibility and contribution questions to a single resource, such as Lively's HSA guide, so answers stay consistent

This is where preparation pays off. Instead of putting out fires, you can focus on helpful, human support that keeps things moving.

Week 2: remind, re-engage, and close the loop

In the second week, shift to follow-ups. Reminders sent now give employees who haven't acted time to finish before the deadline.

• Send nudges to anyone who hasn't submitted forms or logged in

• Post deadline reminders in internal channels (Slack, Teams, company newsletter)

• Re-share the benefits summary or FAQ one-pager

• Clarify the default outcome if no action is taken, such as waived coverage or auto-enrollment

• Confirm how employees will receive confirmation of their elections

Your goal is to help employees complete their elections with confidence. A few well-timed reminders make a real difference.

Final 2 to 3 days: last call and rapid response

As the deadline approaches, question volume and last-minute changes go up. This is your final push to make sure no one misses the chance to enroll and that everything submitted is complete and accurate.

• Send a final reminder with the deadline, what's at stake, and how to get help

• Monitor your inbox closely for urgent issues or corrections

• Be ready to help anyone having trouble logging in or completing an election

• Coordinate with your broker or vendor on when systems close and data locks

• Run a quick check that every employee submitted something, even if it's an affirmation

Staying responsive in these final days helps employees feel supported and reduces errors you'd otherwise fix later.

Post-enrollment phase

Once the window closes, the pressure starts to ease. This is your chance to tie up loose ends and set up a smoother year ahead.

1 to 3 days after: verify elections and send to your broker or carrier

Review employee submissions quickly while the process is still fresh. Small errors now can affect coverage or payroll later.

• Cross-check submissions against internal records

• Flag and correct duplicate or incomplete forms

• Send verified elections to your broker or carrier for processing

• Confirm the timeline for ID cards and plan activation

• Send HSA elections to your HSA provider so accounts can be opened before the plan year starts

Getting this step right helps prevent coverage gaps and builds trust with employees going into the new plan year.

1 to 2 weeks after: communicate what happens next

Employees may still have questions about next steps after OE closes. Answering them before they ask keeps your inbox manageable.

• Let employees know when ID cards will arrive, or how to access them digitally

• Share how to confirm elections in the benefits portal or on a pay stub

• Provide a support contact for post-enrollment questions

• Confirm when new payroll deductions for HSA, FSA, and premiums begin

• Tell employees new to an HSA when their account will open and when the first employer contribution will arrive

The date the account is established matters. An HSA can only reimburse qualified medical expenses incurred after the account is established, according to IRS Publication 969, and state law sets when that happens. In most states, an HSA must be funded to be established, according to IRS Notice 2008-59. For an employee new to an HSA whose high-deductible plan starts January 1, an account that isn’t established until February can’t cover January’s care. Getting new accounts opened and funded before the plan year begins avoids that gap.

Within 30 days: review, document, and debrief

With enrollment wrapped up, take time to reflect. What worked? What didn't? What feedback did you hear from employees or managers? Capturing it now makes next year easier.

• Hold a short debrief with your HR team, broker, or vendors

• Send a quick pulse survey asking employees for feedback

• Document issues with forms, tech, timelines, or communications

• Update your internal OE playbook or checklist based on what you learned

Even a few notes help you build a stronger enrollment process next time.

Continue benefits education year-round

The work of open enrollment carries into the rest of the year. Continuing to educate employees helps them get more value from their benefits and makes next year's enrollment easier.

• Schedule monthly or quarterly benefits tips

• Highlight benefits like mental health resources, HSAs, and wellness programs

• Add benefits reminders to all-hands or manager meetings

• Track recurring questions to improve future communications

Final thoughts

Open enrollment goes smoother when each phase has a plan: data and decisions in the prep phase, steady support during the window, and clean follow-through once it closes. For employers offering an HSA, the follow-through includes one step that's simple to schedule and costly to miss, which is getting accounts open before the plan year begins.

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, and legal professionals, as appropriate, before making any investment or utilizing any financial planning strategy.