The Open Enrollment 2024 Checklist:

Making the Most of OEP & AEP

Learn more about preparing for the insurance sales season and cleaning up your processes to make this the
the best year yet for your insurance business.



To reach their full potential, health insurance brokers and agencies need to be prepared for the open enrollment period, which is when anyone can buy health insurance on exchanges. For virtually all agencies and brokerages, this is the busiest time of the year because consumers and employers can sign up for insurance with no strings attached. That’s compared to special enrollment periods, when people are eligible for insurance due to life changes—such as getting married, having children, losing a job, getting divorced, or moving to a new state. 

If agencies and brokerages aren’t ready to deal with a high volume of calls and website traffic during this period, the odds are that they will leave potential enrollments on the table.


Though the precise dates of the open enrollment period might shift over time, they’ve hovered in the same range for the last several years.


When is Medicare AEP and Open Enrollment for Medicare coverage? The annual election period, or the annual Medicare AEP, kicks off on October 15 and runs through December 7.

Medicare Advantage open enrollment is from January 1 – March 31 and you must have an active Medicare Advantage plan to enroll in Medicare OEP.


When is OEP for 2023 health plans? The open enrollment period kicks off Nov. 1 and runs through Dec. 15, with plans going into effect Jan. 1.

Suffice it to say that no matter how much web traffic you get, how many emails fill up your inbox, and how many prospective or existing clients call you throughout the year, most agencies and brokerages will experience a massive uptick in requests as we move closer to the open enrollment period. That being the case, it is critical that health insurance businesses are ready to handle this influx of traffic.

To do that you need to plan ahead. You need to know the ins and outs of the open enrollment period; stay on top of changes in the law, health insurance plans, and treatment options; figure out how to communicate with clientele effectively to make sure you aren't blindsided by the open enrollment period; and make sure you have the right tools in place to maximize enrollments and revenue.


↓ Keep reading this guide to learn:


  • Why and how to keep abreast of changes in health insurance and coverage
  • How to communicate with your clients to make sure they’re aware of the upcoming open enrollment period
  • How to increase the chances that you maximize your revenue potential during the open enrollment period
  • How technology can help your agency or brokerage work more efficiently while meeting client expectations during the busiest time of the year
  • How to make sure you’re prepared for the Enrollment Periods

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Chapter 1

Preparing for The Enrollment Periods: What You Need to Do


Being prepared is half the victory
- Miguel de Cervantes


If your agency or brokerage isn’t ready for the open enrollment period, how can you expect to sell insurance to every client and prospect who reaches out to you during the busiest time of the year?

The good news is that getting thoroughly prepared for open enrollment isn’t impossible. With the right approach, you can build an insurance-selling machine that meets the needs of your clients while ensuring your sales team isn’t overworked.

Before we dive in, we recommend setting goals to drive your OEP and AEP sales, marketing, and operational efforts this year. We've made templates for you (with examples).


Download Your Goal Setting Packet



With that in mind, let’s take a look at four ways your agency or brokerage can start preparing for open enrollment today. The sooner you master these elements, the better positioned your company will be to thrive during the open enrollment period—this year and for many years to come.


1. Keep track of changes in the law, health insurance plans, and care


Although the open enrollment period is predictable—you can count on it at the end of each year—it’s also unpredictable in the fact that health insurance laws, plans, and care options change every year.


For example, in a partnership with the private sector, last year, the Centers for Medicare & Medicaid Services developed a new enhanced direct enrollment program that enables consumers to buy health insurance coverage on federal exchanges.


This program represents an improvement on the direct enrollment pathway that had been in place since 2013, which allowed agencies and brokerages to help customers find plans on Now, under the enhanced program, consumers can buy Medicare coverage and ACA plans directly from agencies and brokerages like yours on your website. 


When you partner with the right web broker entity, you won’t have to do any heavy lifting to take advantage of this new program. The software will have this functionality enabled during the open enrollment period, reducing time and errors for brokers and agencies looking to sell insurance to clients under these programs. 


This change represents just one major shift in the health insurance industry. With so many changes going on, it is critical to keep track of all of them. Otherwise, you may leave money on the table.


Leading agencies and brokerages stay on top of all of these market shifts so they can be trusted advisers to their clients—as well as great resources for any prospective clients who may reach out with questions.


This all sounds great, but how exactly do you stay on top of such things?


It starts with taking a proactive approach to education. Incorporate continuous learning into your regular workflow to keep on top of what’s going on in the industry. Some easy ways to do that are as follows:


  • Attend popular health insurance conferences to network with industry thought leaders and expose yourself to new ideas and technologies.
  • Listen to health insurance podcasts to stay on top of trends and industry developments.
  • Find a few trusted sources of industry news and check them out periodically.

Do your due diligence to determine which conferences, podcasts, and news sites are best suited to your agency or brokerage’s unique needs. That way, you keep your fingers on the pulse of any major changes in health insurance and healthcare technology—reducing the likelihood that you’ll ever get caught off guard by any major developments.



Grow Your Business2. Communicate with your clientele throughout the year


If you’ve ever bought your own health insurance, you know how overwhelming the experience can be.


You browse a number of plans and do complicated math equations to determine how much yearly premiums will be against how high deductibles, copays, and out-of-pocket maximums are. You need to figure out whether your doctor is in-network or out-of-network, and you need to figure out prescription drug benefits. The list goes on and on, and of course, these numbers and considerations change every year.


Figuring all of that out is a massive endeavor. But wait—there’s more!


Beyond simply determining which health insurance plan makes the most sense for their specific situation, clients also need to keep track of how insurance laws change. For example, the Affordable Care Act’s employer mandate means that a business with at least 50 full-time employees needs to offer health insurance to at least 95 percent of its employees and their dependents who are 26 years old or younger. Otherwise, they could be fined. This is information that a new small-business owner might not be aware of.

Because most health insurance customers simply don’t have enough time to stay on top of all of these changes—and many of them might not be familiar with insurance terminology in the first place—your agency or brokerage should communicate with your clients throughout the year, keeping them informed of all changes in laws and coverage as well as educating them on health insurance basics.

For example, during the spring or summer, you might send out an email blast to your clientele with the following subject line: “7 Health Insurance Terms You Need to Know.” Your email could include a link to a blog post that defines common terms such as deductible, premium, copay, coinsurance, in-network, out-of-network, and out-of-pocket maximum.

We've created email templates that will help you stay in touch with your leads and clients throughout OEP. Save your copy here!

The better you communicate with your clients throughout the year—and the more you keep them engaged—the less likely they will be to get caught off guard when the open enrollment period comes around. And, of course, the more likely they’ll be to buy health insurance from you.



3. Offer ancillary insurance products so you can upsell your clients


Does your health insurance agency or brokerage sell only health insurance? If so, you’re potentially missing out on plenty of money.


Because the open enrollment period puts you in touch with a number of clients, you need to capitalize on the opportunity by trying to upsell them when the opportunity presents itself. Why not present your business as a one-stop shop for all insurance needs? By adding vision, dental, disability, accident, Medicare Advantage, and Medicare Supplement plans to your agency or brokerage’s product portfolio, you can do a better job of meeting your clients’ insurance needs while bolstering your bottom line.


You might be thinking that this all sounds great, but selling health insurance on its own is hard enough. How, then, can you add all of these other insurance products to your portfolio and not get burned out?


Thanks to new tools designed specifically for agencies and brokerages like yours, doing that is nowhere near as hard as you might think.


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4. Use technology to expedite the quote and enrollment process


In the age of smartphones, ubiquitous connectivity, and lightning-fast networks, consumers expect instant gratification and personalized experiences. Thanks to Amazon, they’ve learned that they should be able to buy something the moment they want to buy it—not during some arbitrary block of time when a company happens to be open for business.


This doesn’t mean that your agency or brokerage needs to be staffed 24 hours a day—quite the contrary. 


Thanks to innovative new software solutions, your business can sell insurance products around the clock—even when you’re sleeping.


For example, leading quote and enroll solutions enable customers and prospects to shop and compare health insurance plans at their convenience. This is a big deal—especially considering the fact that 72 percent of clients have looked online for health insurance.


At the same time, these solutions let agencies and brokerages sell insurance plans from carriers across the country. Not only does this give clients and prospects as many choices as possible, but it also makes it easy to add ancillary health insurance products to your portfolio. This plug-and-play approach is much more efficient than hopping from one carrier site to another when a prospect is on the phone.


The open enrollment period is exceptionally busy, but technology can also make sure your team doesn’t burn out.


For example, a customer relationship management (CRM) solution can automate client outreach and repetitive tasks. To illustrate: With a CRM system in place, agents can automatically send personalized emails to all of your prospects and clients, reminding them that the open enrollment period starts in two months. 

CRM Productivity Report

This is something you simply cannot overlook—email marketing is one of the most important aspects of a successful enrollment period. With the right approach, you can gently nudge and remind your clients and prospects that they will need to start thinking about their healthcare needs for the upcoming year. CRM tools can automate this outreach entirely—giving agents more time to focus on other important areas.


By investing in the right technologies, your health insurance business can operate more efficiently and effectively, setting yourself up for success when the busiest time of the year approaches while keeping employee morale high.


Now that you are familiar with some of the more important things you need to do to prepare for open enrollment, let’s shift our attention to some questions you can ask yourself to make sure you’re ready when the calendar changes to November.

Chapter 2

5 Questions to Ask Yourself When Preparing for Open Enrollment

How, specifically, can you figure out whether your agency or brokerage is ready to handle all of the traffic and inquiries that come your way during the open enrollment period? 

Although every agency and brokerage is different—plans and carriers vary on a state-by-state basis, for example—asking yourself these five questions, and being satisfied by the answers, is a good place to start.

1. Do I understand all of the changes in health insurance laws and the industry?


The better you understand the current health insurance landscape, the easier it will be to advise your clients on their best options.

2. Can my website accommodate increased traffic?


If your website can’t scale to support high-traffic periods, clients will get frustrated—to the point where they start looking elsewhere for substitutes.

3. Am I meeting user expectations with convenience, personalization, and instant gratification?


Can clients buy insurance and shop for plans around the clock? Are you engaging with them on a personal basis? If you’re not meeting client expectations, you may have a harder time selling insurance to them.

4. Do I have the tools I need to handle lots of sign-ups for lots of different insurance products?


If your company is still manually searching for plans online and taking every order by phone, it’s impossible for you to sell to everyone who’s interested. By investing in the right tools and technologies, your agency or brokerage can significantly increase its efficiency while selling a wider variety of health insurance products to more clients and strengthening their experience.

5. Is my team up to speed on everything?


You might know everything there is to know about insurance. You might have the best website in the world and a tech stack that is second to none. You might also have a strong portfolio with all kinds of insurance products. If your team doesn’t share your industry expertise—or it doesn’t know how to use the technologies you’ve invested in—you might have a hard time achieving your goals. 


As you prepare for open enrollment, you need to ensure that you are contracted with all of the carriers you will need to work with during the period. You also need to make sure you have appointments in the states where carriers might have established a presence since the previous open enrollment period. When you partner with the right web broker entities that have already established these relationships, this is nowhere near as hard as it might sound.


Chapter 3

Your Open Enrollment Timeline

January-February: Spend some time assessing your company’s situation. Determine how well you handled open enrollment last year and figure out where you can improve for the upcoming year. Is your team staying on top of industry trends? Do you have the right software solutions in place? Can your website scale? These are all questions you need to answer.


March: Now is a great time to be thinking about re-engaging your customers to sell ancillary products. Because your clients are out of open enrollment, you should be communicating with them and assessing upsell opportunities. Ancillary products can be a great way to keep your earnings rolling through the spring. It’s probably a good idea to keep your quoting and enrolling tool, such as Quotit’s software, to make your post-OEP sales cycle easier.


March-August: Keep your clients engaged by regularly communicating with them via email marketing outreach. Use a CRM solution to automatically send clients “happy birthday” notes and let them know about certain milestones—when they’re aging into Medicare, for example. Use email marketing to educate your clients about healthcare terminology, changes in coverage, and other topics that add value to their lives and prove you go above and beyond.


You should be nurturing your prospects and leads and thinking about ways to grow your network and your business. Identify opportunities for cross-selling or upselling. You can do this using technology such as Quotit, which allows your clients to shop for multiple insurance products at the same time on your website.


Aug. 1: Send a quick note to your clients, reminding them that the open enrollment period for the upcoming year is three short months away. Point them to resources that can help them make the best decisions, and let them know that you can solve other insurance needs—such as dental, vision, and disability—too.


Sept. 1: Enrollment is just two months away! Remind your clients and point them to additional educational resources.


October: It’s getting to crunch time! With open enrollment just one month away, reach out to your clients each week (or at least every other week) in October to make sure they don’t forget about it.


Nov. 1: Send a note to your clients, letting them know that the open enrollment period has officially kicked off.


Nov. 1-Dec. 15: Continue reminding your clients that the open enrollment period is underway until they’ve signed up for a plan. You may want to send out notes on a daily basis (or near-daily basis) as the period comes to an end.


After a client has enrolled in a plan, thank them for their business and let them know that you’re always available to answer any questions they might have.


Save this OEP checklist using the image below: 


Are you Ready for OEPAEP Checklist


For more information on how to get the most out of the open enrollment period, visit


Chapter 4

Are You Ready to Make the Most Out of the Open Enrollment Period?

Taking your agency or brokerage to the next level starts with getting all of your ducks in a row so that you’re prepared to maximize revenue during the open enrollment period each year.

To do that, you need to stay on top of changes in the health insurance industry, maintain open lines of communication with your clients, add additional insurance products to your portfolio, and invest in technology that helps improve the client experience while increasing team productivity.


Is your agency or brokerage prepared for the upcoming open enrollment period? If not, there’s no better time to start preparing than today.


For more information on how software can help you supercharge your quote and enrollment processes while helping your team reclaim time and maximize the open enrollment period, check out our products. 


Here’s to a happy, healthy, and productive open enrollment period—this year and beyond!

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