OE Success Tips for Employers of Any Size

When all the painstaking strategizing and analyzing is done and you have selected the benefits packages that work best for your people, it’s time to shift focus to delivering a successful open enrollment (OE). With today’s distributed workforce, engaging and educating employees is more challenging than ever. Tapping into the knowledge and experience of our expert benefits team and many clients, Sequoia has synthesized five open enrollment best practices that successful companies apply to help employees not only navigate the OE process, but also feel valued and supported all year long.

#1: Engage Stakeholders & Employees Early

While it may be too late to apply this tip to your 2023 open enrollment season, it’s valuable to bear in mind as you prepare for your upcoming plan year. The most effective way to ensure a smooth open enrollment is to engage your leadership and employees well before OE is even on anyone’s radar. Taking a proactive approach to planning allows you to incorporate input from key stakeholders, space out actions to a manageable pace, and limit any under-pressure decision making. Here are some key tips for early planning:  

  • Make sure to discuss and agree upon the goals for your open enrollment with your company leadership well before the window opens. These goals can range from increased plan participation, to boosting engagement in specific programs, to aligning benefits with the company culture and core values. 
    • Consider incorporating employee feedback and needs into your goals. Smaller companies can conduct mid-year reviews before your OE to anticipate forthcoming needs and prepare accordingly. Utilize surveys to grasp employee needs and preferences. 
    • Mid to large sized companies may have less flexibility to directly incorporate feedback from a large and diverse employee population. Conduct any feedback sessions or surveys during the summer to ensure ample time to evaluate the results with the intent to incorporate them into your goals. 
  • Try to set the open enrollment window early enough so you have time to plan ongoing communications with employees before and during the process.   
    • A typical OE window is two weeks, but timely submission to carriers is crucial as most benefits will go into effect on January 1st. 
    • Consider that the end of the year is a very busy time for most companies with critical events and obligations. That’s why it’s important to proactively work with business stakeholders on finding the right OE timing to get the deepest engagement. Small companies with small group rates often hold OE from mid-November through early December. Mid-sized companies typically run OE from mid-October to mid-November, while larger companies may start even earlier, possibly in early October.  
    • Some fiscal year variations can lead to OE windows that are only 2-4 weeks before the new benefits take effect. If this is the case for your company, a proactive employee communication plan is crucial. 
  • Proactively communicate important dates and deadlines well in advance so that employees can plan ahead. Add relevant dates to shared company calendars and make sure to establish clear expectations and actions. Important dates include the OE window to select benefits, training sessions for benefits education, and the deadline for benefits selection. 

#2: Tailor Your OE Approach & Messaging to Your Population

When it comes to educating your employees about their benefits and the many ways your company invests in them, some messages will resonate more than others. During the critical open enrollment window, here are some tips to make sure you are bringing to the surface the most relevant messages for your employee population – both as a whole and for diverse subsets: 

  • Diversify your communication channels so that employees can stay informed through the tools they prefer and use most. Make sure you think outside of the email inbox and also communicate via your intranet, Teams or Slack channels, text messaging, and notifications in your benefits portal and/or mobile app. 
  • Also diversify your benefits training and education methods to maximize engagement, even if it means repeating the same information. Some employees may prefer to read about their options ahead of time, some may attend virtual webinars or benefits fairs, some might rely solely on in-office workshops, and some might need one-on-one sessions to address unique circumstances.  
  • Make sure to acknowledge diverse employee needs by highlighting benefits offerings that uniquely address their different geographic locations, worker groups, and life stages. You may even consider conducting separate sessions for various benefit programs instead of overwhelming employees with information overload in a single session. 
    • Cover your healthcare benefits options in a dedicated session and don’t overlook carrier programs that often come bundled with medical plans.  
    • For those considering or raising families, cover in detail your various family-forming, family-supporting, and leave benefits. 
    • Those who are starting their career or nearing its end might value a special session on the ins and outs of using retirement benefits smartly. 
    • Consider a special session covering the value of mental health benefits and those that promote employee wellbeing, particularly for a younger, tech-oriented workforce. 
  • Recognize that the focus of OE education sessions may vary based on the company’s context. Some might focus on highlighting key changes, some might emphasize new plans, while others might dedicate time to emphasizing unique perks and wellbeing strategies. 
    • Larger companies typically cover a more extensive range of topics, while smaller ones might stick to the basics like covering healthcare and retirement plans in detail.  
    • Be sure to clearly communicate any plan updates and changes that will affect employees and their families. If there are plan changes, consider leveraging utilization reports so that you can identify and target groups who will need to participate in an active enrollment and make new selections. 
  • Anticipate common objections and obstacles that employees might raise during OE education sessions. Equip yourself to address these concerns effectively, possibly pointing people to a digital FAQ, to maintain focus and time efficiency. Address issues like cost increases and program changes proactively but without consuming excessive meeting time. 
  • Avoid “one and done” communications. Embrace the fact that benefits education should continue throughout the year, beyond open enrollment. 

#3: Get Creative About Engagement

In a work environment where job performance, competing priorities, and work-life balance are top of mind, employee attention is hard won. Getting them to take notice and action during open enrollment may feel like a losing battle. To set the tone for (or reinvigorate a lackluster) open enrollment, you’ll need some creative ways to reach your people. Here are some ideas: 

  • Open enrollment is a great time of year to boost morale and employee engagement with techniques that align with your company culture. What works to get your people excited during all-hands meetings or offsites? Consider employing the same tactics. 
  • Don’t underestimate the power of incentivizing participation and engagement through coveted company swag, raffles, prizes, and food/snacks.  
    • For smaller companies. consider bringing in local food vendors or organizing an engaging event to boost participation and enthusiasm among employees (i.e puppies!) 
    • For larger companies, consider organizing specific events across all locations or incorporating milestones into the presentation and prizes to ensure an exciting experience for everyone. 
  • Want to keep employee attention on important OE actions? Consider keeping sessions concise and focused on specific topics. See Best Practice #2 above for some guidance.  
  • Utilize personalized/relatable approaches and appropriate humor when presenting various plan options.  
    • Small companies can gamify their education sessions, employing fun trivia to highlight aspects of their benefits packages. 
    • For larger companies, integrating real-life employee stories and experiences into your presentations may aid in making the material more relatable and personalized to the audience.  

#4: Use Data to Your Advantage

Open enrollment is a great time to showcase all the benefits your company is proud of and how they are used by your employees. The proof is in the data. As part of a successful open enrollment strategy, you should use your data to help you plan better, execute masterfully, and refine continuously. 

  • Having a plan to track success metrics related to your OE goals is important. Make sure you can measure what you are trying to achieve in your system of record. 
  • In particular, make sure to track metrics and insights related to participation rate, enrollment completion rate, understanding which geographic locations have higher adoption rates, benefit type utilization, monitoring traffic on the enrollment platform, and measuring engagement in informational sessions being offered.  
  • When you use a tool that helps you benchmark your benefits offerings against what other companies are doing, you can use this data to showcase to employees the strength of your offering. Show the comparative data during your OE education sessions in a consumable way that quickly gives them confidence in the plans you provide.  
  • Analyzing data as you build a diversified benefits portfolio will also help you maximize cost savings. For companies that want to reinforce cost-saving strategies during OE, focus on calling attention to – and even incentivizing the selection of – alternative plans like High Deductible Health Plans (HDHP) with Health Savings Account (HSA) options. You can guide smart employee decision making by sharing data that shows them how these plans not only align with their needs but are also good for the company. 
  • Make sure you understand how your chosen technology platform can help you streamline and enhance the OE experience. If it’s not obvious, talk to your technology success representative for guidance. 
  • Conduct a post- OE meeting with your company leadership to highlight the changes and potential cost savings made by aligning employees with the most suitable plans, not just the most readily available.  
  • Implement surveys or feedback mechanisms to evaluate the employee experience during open enrollment. Use that data to inform next year’s efforts. 

#5: Maintain a Year-Round Mindset to Benefits Engagement

Open enrollment happens once per year. But the effort involved in preparing for and executing this important event should be leveraged to help keep benefits top of mind well beyond the two-week window. Here are some easy ways for you to keep your people engaged in their benefits all year: 

  • A centralized platform or portal that offers comprehensive benefit details, FAQs, and resources for easy employee access – whenever they need it – is a must for today’s modern employer.  
  • At the same time, optimize your benefits information for mobile access – ideally through a mobile benefits app – ensuring employees can easily review and understand their benefits on the go. 
  • Consistently emphasize the people who care for your employees and their benefits needs: employee advocates, care concierges, claims experts. This repetition ensures that employees are well-versed with the resources available to them after open enrollment. 
  • Provide ongoing educational resources and support that include Lunch & Learn sessions, videos, webinars, and guides tailored to plan changes and benefit options. 
  • In the case of turnover or new leadership, benefits brokers can provide onboarding refresher sessions for new HR or decision makers, ensuring a smooth transition and understanding of the benefits partnership.  
  • Take advantage of the help provided by your brokers, vendors, and carriers throughout the year and pass on their helpful flyers, webinars, and other resources to employees. 
  • Continue communicating reminders about important benefits-related events and deadlines around retirement contributions, FSA/HSA deadlines, etc. Keeping up a consistent stream of communication establishes trust with your employees. 
  • Record your OE sessions so that you have valuable content to use when hiring outside of renewal season. 

At Sequoia, we have a client-centered commitment to come through for those who put their trust in us. We hope that your benefits renewal season goes well. If we can be of any help in the new year, please let us know!


About the Authors:

Gracie Slattum, SPHR, GPHR — As a tenured PEO HR Business Partner, Gracie has built trusted relationships with her clients, ensuring they are compliant and educated on current employment laws and requirements throughout a dispersed workforce. Gracie supports her clients with their strategic business initiatives through best practices and expert knowledge and strives to make an impact on the future growth and success of their organization, ultimately gaining a competitive advantage within their market and industry. In her free time, Gracie will almost always be found outdoors, from her kid’s sports games, fishing, golfing with her friends, relaxing at the beach, and going to as many Padres games as possible. 

Jackie Sinnott has been with Sequoia for over 10 years, all of which have been spent in the Client Service space. She recently moved into a Lead Client Service Manger role, where she works with her team to ensure Client Service Managers have the tools and processes in place, to deliver top results for our clients. Jackie lives in the San Francisco Bay Area with her husband, two daughters and all of their matching dresses and accessories.