Open enrollment doesn’t have to feel like a never-ending maze of forms and fine print. It’s the annual chance for employees to take control of their health care coverage, align benefits with real-life needs, and save money in the process. HR teams that simplify this enrollment process make a world of difference for employee satisfaction, and yes, a little creativity goes a long way.
For HR leaders and benefit managers, linking to resources like wellness gifting ideas for HR teams ensures they have everything they need in one place. The easier you make it to compare options, the more likely employees are to enroll on time and with confidence.
Understand the Open Enrollment Period
Open enrollment is the once-a-year chance for employees to adjust their benefits, most often in November or December. Miss the window, and you’re generally locked in until next year (unless a major life event qualifies you for a special enrollment).
What Eligible Employees Can Do During Open Enrollment
- Sign up for or switch health insurance plans
- Adjust coverage levels
- Add extras like dental, vision, or life insurance
Smart HR teams keep the enrollment process simple with clear reminders, a company intranet hub for resources, and yes, creative touches like branded swag or wellness kits that make deadlines feel less daunting.
Compare Health Plans Without the Overload
When reviewing health insurance plans, employees don’t just need to know the monthly premium; they need the big picture: deductibles, out-of-pocket maximums, and whether their favorite providers are in-network. A clean, side-by-side chart (bonus if it looks good) does the trick without drowning people in jargon.
Think Beyond Health Insurance and Benefits Offerings
Diversify Your Channels
- Company intranet or benefits portal
- Email reminders
- Slack or Teams updates
- Text nudges for key deadlines
Teak & Twine’s curated gift boxes transform open enrollment from a paperwork chore into a memorable moment. Whether it’s a wellness kit that inspires preventive care or a stress-relief package that shows real care for mental health, these design-forward gifts help employees feel supported, valued, and motivated to engage with their benefits.
Start Early and Repeat Often
Employees need plenty of reminders to process benefits changes. Start communication at least a month before the annual enrollment period opens and keep the momentum with countdowns like ‘10 days left to enroll.’
Studies show employees often need to see or hear a message 5–7 times before acting, so spread updates across email, Slack, and meetings to meet people where they are.
Encourage Two-Way Communication
Don’t just push information out, invite feedback. Set up surveys or polls to learn what employees find confusing about the enrollment process. When employees feel heard, they’re more likely to trust HR guidance and make better, informed decisions about their health care coverage and new benefits for the upcoming year.
Short Videos and Infographics
Not everyone has the time or patience to wade through a 30-page PDF. Visual content breaks down complex information into quick, snackable insights.
- Videos: Two minutes on how deductibles work beats a dense guide.
- Infographics: Use color coding for cost levels, icons for doctor visits, prescriptions, and ER care.
- Stories: Showcase how real employees saved money or got better coverage by switching plans.
Keep content conversational and approachable. Animation, testimonials, or short explainers all help employees understand the enrollment process without needing a law degree.
Live Q&A and Office Hours
Even with great resources, employees will have questions. Hosting Q&A sessions, virtual or in-person, gives them a chance to ask directly.
- Offer both group and one-on-one sessions.
- Record sessions for later reference.
- Invite reps from the insurance company to clarify tricky coverage details.
Encourage questions in a judgment-free zone. Employees should feel comfortable asking basics like “What’s a copay?” because those answers shape real decisions.
Strengthen Engagement with Branded Gifts
Enrollment can feel like a paperwork overload. That’s why thoughtful incentives change the game. Companies that use branded gifts during open enrollment show employees their participation is valued, not just required.
Custom corporate wellness gifts that double as both rewards and reminders can make enrollment feel more meaningful. Imagine: employees who attend an info session receive a beautifully packaged kit with a fitness tracker, a reusable water bottle, and healthy snacks. Each item reinforces the idea that the company cares about more than just insurance coverage.
Creative Ways to Encourage Employees
Open enrollment can feel like one more chore on a long to-do list. That’s why the smartest companies mix education with a touch of fun. Ideas include:
- Hosting a “benefits fair” with interactive booths where employees spin a wheel for prizes (like gift cards or small branded items).
- Offering team competitions for fastest completion rates, with winners receiving a premium gift box.
- Sending teaser emails with clues about prizes or surprises to build momentum before the enrollment deadline.
These engagement strategies help employees understand their benefits while giving them a reason to participate early.
Align Gifts with Messaging
- Promoting preventive care? → Wellness journals or meditation apps.
- Highlighting mental health benefits? → Stress-relief gift boxes with aromatherapy and cozy touches.
- Celebrating engagement? → Curated care packages that reflect company culture.
Timing matters too. Offer early-bird incentives, mid-period motivators, and finale rewards for full team participation. This keeps momentum going all the way to the enrollment deadline.
Company Swag for Eligible Employees
Company swag can be a powerful motivator when done right. Forget the generic pens. Employees want thoughtful, high-quality items that actually improve their day-to-day lives.
For remote teams, gifts like The Home Office set are a win. Think notebooks, coffee, and a branded mug that actually gets used. These practical, design-forward touches make the enrollment process feel more personal.
Picture limited-edition enrollment swag: branded athletic gear for companies pushing wellness, or remote-work kits that tie into flexible spending account perks. The exclusivity makes employees eager to participate.
Teak & Twine helps companies design curated, premium swag that doesn’t just collect dust. From artisanal treats to design-forward office upgrades, the focus is always on quality. That investment translates into higher employee satisfaction and way better participation rates.
Think Long-Term Value
The best enrollment swag isn’t just trendy; it’s useful year-round. Employees appreciate gifts they’ll use daily, which also keeps benefits messaging visible. Popular options include:
- Tech accessories: Wireless chargers, high-quality earbuds, or branded laptop sleeves.
- Wellness gear: Yoga mats, resistance bands, or desk-friendly posture tools. Wellness-focused companies can also lean into curated experiences, like The Work Life Balance package or the Self Care box, which extend wellness support beyond the office.
- Sustainable items: Reusable totes, eco-friendly drinkware, or solar-powered chargers.
When paired with thoughtful communication about benefits offerings, these items reinforce the company’s investment in employee well-being. The best swag balances practicality with style, so your gifts don’t just get tossed in a drawer.
Showcase New Benefits with Swag
If your company is rolling out new benefits during the upcoming year, design swag that ties directly to those offerings. Launching a mental health initiative? Gift mindfulness kits. Expanding fitness coverage? Deliver branded gym bags. This direct connection between swag and benefits coverage helps employees immediately understand and engage with new resources.
Let’s Make Open Enrollment Work
A successful open enrollment isn’t about drowning employees in documents; it’s about empowering them to make informed decisions with confidence. From breaking down benefits to building engagement with creative incentives, small changes make the enrollment process smoother and more impactful.
Partnering with experts like Teak & Twine takes it a step further. Their custom gift boxes and strategic approach turn open enrollment into more than a task; it becomes a chance to connect, show care, and spark excitement. Because honestly? Your benefits deserve better than boring.
FAQ
You might be wondering...
How to Have a Successful Open Enrollment with Teak & Twine?
Start early, highlight major benefits changes, and use clear communication. Pair information sessions with Teak & Twine’s curated gifts to encourage employees and keep enrollment energy high.
How to Make Open Enrollment Fun with Branded Gifts?
Gamify the enrollment period with raffles, scavenger hunts, or bingo cards, and reward winners with unique gift boxes that reinforce wellness and team culture.
What Happens If I Do Nothing During Open Enrollment?
Usually, your current coverage rolls over automatically. But you may miss out on new benefits, lower premiums, or better cost options.
What Do I Need to Do for Open Enrollment?
Confirm available plan options, compare health insurance plans, review enrollment terms, and weigh costs like premiums and deductibles. If your employer offers swag or engagement rewards, don’t miss out; they’re designed to make the process smoother.
