Open Enrollment 2024: The Power of Early Preparation

4 people working on a project together- Open Enrollment 2024 blog featured image

The job market remains highly competitive as employers work to attract and retain today’s top talent. With the open enrollment 2024 season quickly approaching, employers can develop attractive benefits offerings and proactively communicate with workers to win them over. Early preparation can help show employees they are valued, convince top performers seeking job changes to stay in their current positions and attract new talent. 

By starting open enrollment efforts early, employers will have ample time to tailor their benefits offerings and thoughtfully showcase all employee perks. Consider these steps to begin today.

Steps to Prepare for Open Enrollment 2024

1. Tailor benefits options.

Employee benefits offerings can serve as powerful attraction and retention tools. However, that’s only true if workers see value in these offerings. That’s why employers should tailor their benefits options to include perks employees care about ahead of open enrollment.

Debates around remote, hybrid and in-person work continue between employers and workers, and some workers are willing to make employment decisions based on retaining flexibility in when and where they do their jobs. Additionally, many organizations have a renewed focus on employees as people and have been prioritizing employee well-being. More than ever, workers want to feel like they belong in the workplace and feel recognized, appreciated and safe—and employers are poised to deliver on those needs.

Various surveys and reports have found that the following are some of the top benefits employees want:

  • Greater compensation
  • Remote or hybrid work environments
  • Flexible or hybrid scheduling (e.g., four-day workweeks)
  • Paid leave policies
  • Mental health resources
  • Family-building and reproductive health benefits
  • Caregiving benefits
  • Professional development opportunities
  • Financial wellness resources

2. Determine key messaging.

After solidifying benefits options, employers need to plan their messaging and communication strategies. For 2024, key messaging might focus on new or updated benefits offerings, as well as these offerings serving as incentives for employees to stay in their current positions.

Putting benefits front and center can compel employees to weigh the advantages of searching for new jobs against guaranteed perks. Employers should detail their offerings so employees understand everything they could potentially lose by changing jobs. Touching on these details is particularly important, considering that 1 out of 3 workers don’t understand the benefits they elected during open enrollment, according to Voya Financial. This means some employees may be job hunting for perks that they already have access to.

Benefits communications should account for employees’ desires to feel safe and secure by demonstrating how workplace offerings can protect them. As employees’ needs vary, outlining different benefits offerings can help them understand which benefits they need and will likely use. Employees’ appreciation for benefits may improve when they can choose benefits plans tailored to their specific needs. The more appreciative employees are, the less likely they are to seek other job opportunities.

3. Communicate about benefits.

Employees want more help understanding their options, so employers should share information early, provide educational resources and have multiple communication channels. An effective open enrollment communication strategy may include the following components:

  • Group meetings to discuss available benefits
  • One-on-one meetings to go over any questions
  • Multichannel communication methods (e.g., videos, printouts, guides, presentations, emails and comprehensive guides)
  • Periodic enrollment reminders, including enrollment dates and workplace-specific instructions
  • Messaging that directs employees to designated points of contact for questions (e.g., HR)

Leveraging technology allows employers to communicate more frequently and effectively with employees. With more employees working remotely, virtual enrollment may be the most feasible option for many employers, saving them time and resources.

Early open enrollment communication gives employees more time to understand their benefits. Although year-round communication is ideal, employers can amp it up for open enrollment. The recent Consumer Engagement in Health Care Survey revealed that although many Americans are satisfied with the open enrollment process, they are not looking closely at their health plan options when making selections. Nearly three-quarters (72%) of adults spent less than one hour deciding on their health plan during open enrollment. A better understanding of offerings may help employees make more active choices in their health plans during the open enrollment season and beyond by helping them understand the perks of staying with the organization.

Don’t Worry About Communicating Too Soon About Open Enrollment 2024. 

Repetitive messaging and reminders increase the odds of employees seeing necessary information and understanding their benefits. Reach out to us for additional open enrollment 2024 information and resources.


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Rob Wagner

Executive Vice President | Director of Sales, Southeast Region

With over 15 years of insurance industry experience, Rob focuses on growing organic growth throughout the entire Southeast region for both Acentria Insurance and Foundation Risk Partners. Working alongside both executive leadership and territory sales leaders, Rob is instrumental in producer training, increasing retention and expanding our organizational footprint.

As a self-proclaimed Army Brat, he was born in Fort Benning, GA, but has moved 27 times and resided in 40 different houses… all before college! His father proudly served our country for 28 years! As a graduate of Florida State University with a degree in Business Management, Rob also holds an MBA from Stetson University. A producer at heart, he specializes in large property, senior living, management liability and workers’ compensation. He enjoys meeting new team members and finds his personal success in seeing producers succeed.

In his free time, he enjoys spending time with his wife of 22 years and their two daughters. Together they enjoy boating, offshore fishing and exercising.

Mike Freeman

Mergers & Acquisitions

Leading the Acentria Mergers & Acquisitions team, Mike works with those agency principals and leaders who are interested in furthering a potential partnership with Acentria Insurance.  With over 35 years of finance and insurance experience, Mike and his team showcase the various benefits of partnering with Acentria. He works with principals through the initial phases to evaluate agency operations, books of business as well as planning and implementing fully comprehensive migration and implementation plans. He served 25 years in the banking industry in various executive-level positions transitioning to insurance in 2011 as Chief Financial Officer for Acentria Insurance. In 2017, Acentria Insurance partnered with Foundation Risk Partners where his major focus became leading Acentria Insurance’s mergers and acquisitions team.  

Mike is a graduate of Auburn University. He is dedicated to serving his community having held numerous leadership positions including Chairman for the American Heart Association; Chairman Mental Health Association; Chairman Destin Chamber of Commerce and Board Member for United Way Okaloosa-Walton Counties. Mike is a 27-year resident of Destin, FL and enjoys spending time with his wife of 35 years, Yvonne and their two adult children and their families.

Jenny Cirioni

Vice President, Operations
Northeast, Florida

Todd Lawrence

Executive Vice President
Southeast Florida

Rob Wagner

Executive Vice President
Southwest Florida Region

Alan Florez

Executive Vice President, National Sales

Alan leads new business growth strategies and expansion, guides the development of resources and training for Sales Producers and their partnerships with Carriers. With over 15 years of industry experience, Alan also leads the Acentria Public Risk divisions working with municipalities and government entities for their coverage needs. He was appointed to the Halifax Health Board of Commissioners December 2020 and also serves as an Executive Committee member for our parent company, Foundation Risk Partners.

Previously, Alan served as Governor Jeb Bush’s Deputy Director of Legislative Affairs and Special Assistant. He is a former member of the University of Central Florida Board of Trustees and currently volunteers his time with the Florida Council of 100, Futures Foundation of Volusia County Schools and the Community Foundation of Flagler and Volusia. Alan holds a bachelor’s degree in Political Science from the University of Central Florida.

Anne Kraus

Senior Vice President
Commercial Lines Operations

Teresa Fillmon

Vice President
Small Business Unit

Alex Doberstein

Vice President
Benefits Resource Leader

Eric Austin

Operations Lead
Port St. Lucie & West Palm Beach

Luke Wolkers

Executive Vice President
Employee Benefits

Chris Tolland

Executive Vice President
Northeast Florida Sales

Brian Stanton

Executive Vice President
Southeast Florida

Nathan Marks

Executive Vice President
Northwest Florida

Jason Cruse

Executive Vice President
Central Florida Sales

Jackie Shaw

Senior Vice President
Agency Operations

Jessica Parkhurst

Senior Vice President
Marketing & Branding

Doreen Castro

Senior Vice President
Personal Lines Operations

Kendall McEachern


Kendall was a fundamental part of Acentria Insurance. As a co-founder, he brought more than 30 years of industry expertise to Acentria, helping transform the organization into a leading insurance provider. Beloved by team members, carrier partners and clients, he oversaw more than 400,000 insured multi-family units with property values greater than $22 billion, and over four million square feet of commercial office space and real estate buildings. Kendall has received numerous industry awards to include being recognized as a National Top Producer and Agent of the Year by both Insurance Business America and Insurance Journal. Away from the office, he served as chairman for the American Heart Association, actively participated in his church and golfing, watching sports and spending time with his family. Kendall passed away in January of 2021, leaving a lasting legacy on Acentria’s culture, success, industry-wide reputation – and on all of us fortunate to have worked alongside him.

Mary Lawless

President & Chief Operating Officer

As President and Chief Operating Officer, Mary brings over three decades of industry expertise to Acentria Insurance. With a strong focus on Mergers & Acquisitions, Mary is passionate about partnering with new agencies and leaders to continue the overall upward growth of Acentria. She works in conjunction with the CEO to lead and deliver specialized sales products, services and industry leading capabilities while implementing business and sales strategies to the Acentria sales team and carrier partners. Mary has direct oversight of all operational leaders throughout the entire organizational footprint and is responsible for operational financials and budgets.

She empowers her team members and because of it, is well respected by her peers and those she leads. Since her time with Acentria, Mary’s leadership has contributed to the agency’s exponential growth from 15 to well over 50 locations, increasing employment to over 700 team members, across the southeastern United States. Due to her leadership and contributions to the insurance industry, she has been nationally recognized as one of Insurance Business America magazine’s Elite Women and serves as a valuable member on the Executive Committee for Foundation Risk Partners, Acentria’s parent company. Prior to joining Acentria Insurance, Mary led operations for another national broker. Throughout her tenure, she has held a variety of management positions in Personal Lines, Select Business and Employee Benefits. Mary specializes in agency operations, partnerships and acquisitions and is truly passionate about developing team members to become great leaders.

When not shaping the future industry leaders at Acentria Insurance, Mary enjoys traveling and spending time with her husband, Pat and their family and friends.

Mitch Weinstein

Partner & Co-Founder

As partner of Acentria Insurance, Mitch plays an integral role in mergers & acquisitions. He focuses on seeking out strategic like-minded partners and agencies, across the southeastern United States, to partner and join the Acentria family.

Mitch has over 42 years of business leadership experience that ranges from law enforcement to the finance, healthcare and insurance industries. He was instrumental in developing the nation’s first “at-risk” managed care network for physical and occupational therapy serving the worker’s compensation industry. This network paved the way for a new managed care system, based on incentives.

Mitch is passionate about giving back to the youth of his community. He is an active supporter of the Boys & Girls Clubs of Polk County and believes in helping all young people reach their full potential. He is also the founder of Fallen First Reserve which is a non-profit organization dedicated to financially assisting those family members of First Responders killed in the line of duty and military members killed in action. Mitch also serves on the board for Fund the First.

Kevin Mason

Chief Executive Officer & Co-Founder

As Chief Executive Office of Acentria Insurance, Kevin focuses on developing insurance solutions that strengthen Acentria’s presence in the market and its commitment to client-relationships and exceptional service. With over 35 years of industry experience, he specializes in the overall growth of Acentria is passionate about bringing new talent to the organization both organically and through mergers and acquisitions. Through his leadership and the support of the Executive Leadership team, Acentria Insurance instills a positive corporate culture which has led the agency in being recognized as a leader within our industry as a Top 100 Workplace, Employer of Choice, Best Agency to Work For and several other national and regional accolades.

Before co-founding Acentria Insurance, Kevin served as Branch Manager for another national broker. Kevin holds the prestigious title as an Agent of the Year and five-time National Top Producer. He is also a key member of the Foundation Risk Partners Executive Committee, which is the parent company of Acentria Insurance, while also serving as the National Director for Carrier Relations. In addition, Kevin oversees the Sales Leadership Council, which encompasses sales leaders across the entire FRP footprint in an effort to develop and refine shared resources while offering producer training and development programs.

Kevin received a Bachelor’s Degree in Management from the University of West Florida. He is very active in his community and served over a decade on the Board of Directors of Destin Charity Wine Auction Foundation and remains as a trustee, which funds over 14 children’s charities along the Florida Panhandle. He is also a member of the Destin Chamber of Commerce, Community Association Institute and Florida Association of Insurance Agents. In his spare time, Kevin enjoys golfing, tennis, boating and spending time with his wife Laura, and their children.