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When Enrollments Go Sideways: Building a Year-Round Communication Plan

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Employer Services

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Lifestyle Spending Account (LSA)

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Why Successful Open Enrollment Begins 90–120 Days Before Enrollment

by Brian Hugger | Jun 19, 2026 | Benefits, Workforce | 0 comments

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It is prudent to point out that within the benefits industry, brokers and carrier reps work hard to acquire new clients and keep them satisfied, but will focusing on new business drive the best overall results? Did you know?

  • 82% of companies agree that retaining an existing customer Is significantly less expensive than new client acquisition.
  • The average retention rate between companies/clients and their insurance brokers is approximately 84%. Much better than average compared to other industries.
  • It is up to seven times more expensive to acquire a new client rather than retain an existing one.
  • 89% of companies see customer experience as an essential factor in driving customer loyalty and retention.

As a trusted third-party administrator to our broker and carrier partners, we are occasionally asked for best practices to help maximize open-enrollment success. Most insurance professionals can likely recall an enrollment they were involved with when a case where much collaboration, planning, and work was exhausted, only to realize lackluster results.

This can leave even the most tenured insurance professional puzzled trying to examine what went wrong along the way. It is worth mentioning that much attention is put into the enrollment itself, but there is much to be gained all around when enrollments are viewed more as an all-encompassing strategy with the goal of exceeding customer needs and expectations, helping the results themselves being a result of a well-delivered and executed model. The most optimum results will likely be the product of a repeatable system with flexibility based on the individual needs of the client.

It is in the spirit of helping benchmark best practices to help brokers and agents make the greatest impact for their clients and succeed while doing it, that we compose this newsletter. Here are some key considerations when it comes to success in the open enrollment best practices within the employee benefits arena:

Start Planning at least 3 to 4 months from Enrollment Date: During the client acquisition stage, it is important to fully understand the needs and values of the organization and ensure you have the tools at your disposal to move forward and that you are aligned with each other. Communication takes time and often repetition to be effective, be sure to allow enough time from solution selection to enrollment, in order to adequately communicate the enrollment expectations and details. Brokers and carrier reps need to be mindful not to get stuck in a practice of utilizing the same strategy for all clients in their book, the “cookie-cutter, one size fits all” approach is no longer going to help you get the desired outcome and drive the strong relationship with the clients that you desire. Clients today have high expectations; and one expectation they have is to be presented with personalized offerings and a variety the methods of communication to the group. The objective is to fulfill each individual set of needs and values the organization specifies. It is also important to recognize if the potential client is not a match for your services. It is better to move on from a potential client, than force a bad fit. The same care must be give to existing clients, it is wise to plan ahead and meet with the client 3 to 4 months in advance of the enrollment target to learn what has changed, discuss engagement, and determine what adjustments should take place from the prior enrollment considering this new information.

One of the most important parts of any benefits enrollment is consulting with the client to better comprehend their: needs, values, wants, goals of offering benefits, etc. A thorough review of what has worked in the past, what has not, what challenges they are facing, what changes they are anticipating, what obstacles they tend to combat are all essential pieces to the puzzle to find the best solutions that may fit their needs. Communication is the key within each step of this process. Let us unpack some key considerations.

There is so much more than simply communicating the offering to the group and the method of informing and educating the employees or members of their options in a brief group meeting with one-on-one Q&A. The enrollment should be introduced to the employees or members ahead of the enrollment, and in a variety of ways. It is also very important that each employee or member has the same opportunity to learn their options and the same access to the information that others have. Prior to choosing products for the employees or members, it may make sense to seek feedback from the population by way of surveys of what their needs and wants are for benefit options.

Once an agreed upon benefits offering is selected, a plan must be made and implemented to inform and educate employees. This should outline when, where, how, why and what they are deciding is a fit for their individual and family needs. Not only of the benefit options being made available to them, but also the timeline and method they will become educated and select from their options, how and when they can enroll, with clear deadlines to have decisions submitted by.

Brokers must focus on offering personalized benefits packages that cater to the diverse needs of a multigenerational workforce and leverage technology, such as AI, to streamline the enrollment process, when appropriate. The needs of the customer and the demographics of its employees and members must be the driving force behind the solutions brokers present. Additionally, effective communication strategies that educate employees about their benefits and encourage participation are essential for successful enrollment. AI can be utilized to help mitigate enrollment questions or assist in selecting the right plan levels for the employee or member’s situation, as well as expedite claims processes to name a few.

A methodical approach to this benefits process will optimize for a successful campaign, and a well-executed strategy sets the tone for a successful open enrollment.   Employee benefits enrollment requires coordination with insurance carriers, employers, HR professionals, Unions or Association executives, enrollment platforms, TPAs, to name a few; regarding offerings, enrollment dates and locations of enrollments, marketing materials etc.  Again, this process should start at least 3 to 4 months prior to an anticipated enrollment start date. 

Up next: Part 2 of 4, “When Enrollments Go Sideways: Building a Year-Round Communication Plan.” Planning sets the stage, but communication is what makes or breaks an enrollment. Next, we look at how to keep clients and their employees informed and engaged at every stage of the year.

Author: Brian Hugger

With over 25 years experience in various leadership roles, Brian has developed a keen instinct and advanced skills making him an effective leader and communicator across many industries. Experience in Employee Benefits, Human Resource, Recruiting, Insurance, Retail management, Manufacturing, Project Management, Customer Service, Data Integrity, Analytics, Consulting, Sales management and Insurance Sales. This experience has developed Brian to relate with the needs and find creative solutions of various clients. Brian is a strong communicator and exemplifies ethical leadership with honesty, integrity, and compassion.

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