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Open enrollment can be hectic for small business owners, who often handle human resources on their own (and sometimes offer enrollment for employment-sponsored benefits in the same calendar window). From fielding healthcare coverage questions to ensuring federal compliance, there’s a good chance you’re stretched thin as you juggle this critical aspect of employee care with the daily demands of business.

This window to enroll in or change individual healthcare plans for 2021 starts on November 1st this year for both private health insurance and Health Insurance Marketplace options. Just in time for the holidays! The good news is that there are steps you can take toward a more seamless open enrollment period.


An easier open enrollment season starts now. Here are just a few of the things you can do to prepare:

  • Request 2021 enrollment forms and learn about any coverage changes.
  • Begin reminding employees, on a reoccurring basis, that open enrollment is coming.
  • Create open enrollment packages with essential information. In September, distribute those packages and encourage staff to start making elections and asking questions.
  • Set time aside between now and open enrollment’s deadline (deadlines vary from state to state) to address employee questions or concerns.
  • Help offset a last-minute rush with fun incentives for employees.
  • Kick off the enrollment process sooner rather than later!


Today’s healthcare landscape is complicated. Don’t assume that common terms – like premiums and deductible – or the difference between PPO and HMO are understood by all employees, or that they’re clear on comparing and choosing coverage plans. A friendly forum that walks through basics is a great way to clear up confusion and help employees take ownership of their benefits (not to mention their overall health). Distribute a survey beforehand to determine which information is most needed. If answers vary wildly, consider a handful of sessions that progress from simpler concepts (like terminology) to more intricate concepts (like the fate of HSA funds once an employee turns 65). The more employees know the more open enrollment legwork they can do themselves.


Health benefits are a high-stakes game. From the wellbeing of your employees to penalties stemming from non-compliance, there’s a lot riding on open enrollment. offers a variety of resources, and private carriers should be willing to get you up to speed, too. Make sure to prepare for common employee FAQs:

  • Questions related to dependents, including new babies, marriage, or divorce.
  • Questions about extended coverage, such as dental, vision, life insurance, or disability insurance.
  • Questions about preventative care, such as screenings for blood pressure, mental health, and autism.
  • COVID-specific questions related to telehealth, FMLA – and health-adjacent conversations that often stem from them (remote working, childcare, sanitization, etc.).

Individual and family health insurance plans available during open enrollment offer employees the opportunity for more customized and affordable coverage options than what they’d get with an employer-sponsored group plan. They also theoretically save small businesses money – the reason more and more companies are encouraging employees to take this individualized route.

Many business owners often overlook a critical detail, however: Group health options give small businesses access to sizable government subsidies like QSEHRA that can reduce the cost of coverage immensely – on average, by 70%. Even more, small businesses can enroll in group health insurance plans at any time of the year. No need to wait for open enrollment!

Want to get the ball rolling now? Reach out to your broker to learn more about group plans and the subsidies available to you or contact us at: (215) 240-1263.