Your Partner in
Benefits Success
At Explain My Benefits (EMB), our mission is to remove the complexity from open enrollment and all employee-related benefit needs so HR administrators can focus on their people, not the process.
Who We Serve
BROKER PARTNERS
As an extension of their team, EMB delivers world-class technology and innovative enrollment and communication solutions, providing tailored support while addressing client needs and challenges efficiently.
EMPLOYERS (Clients)
EMPLOYEES
EMB supports employees with intuitive tools and clear communication that simplify benefits enrollment and ongoing management. We provide easy access to plans, resources and support, empowering employees to make confident benefits decisions year-round.
Driven by Our People. Defined by Dedication.
Meet Our Executive Team
David Howes
President
David is the co-founder of Explain My Benefits (EMB). As an active partner in the business, he is deeply committed to achieving Workplace Benefit Excellence for all brokers that partner with EMB. Founded in late 2007, EMB has grown significantly over the years, and David continues to be inspired by the exceptional people who make up the EMB team.
David earned his Bachelor of Science from Miami of Ohio University in 1992. He proudly served as Captain in the Air National Guard from 1994 – 2004, flying C-130 aircraft and completing two tours of duty in Afghanistan and Iraq. During this time, he also worked as a commercial airline pilot for US Airways Express and Delta Airlines from 1999 – 2001.
David’s insurance career began abruptly following the tragedy of 9/11, when he was furloughed by Delta Airlines in November 2001. He entered the industry as a Benefits Enroller and, between military deployments, continued to enroll and build strong relationships across the benefits landscape. In 2004, he retired from the Air National Guard and became a full-time Allstate Benefits Specialist, supporting insurance brokers throughout Central Florida prior to founding EMB.
Originally from Ohio, David now resides in Oviedo, FL with his wife and daughter. He most enjoys vacationing and spending quality time with his family. David’s hobbies are saltwater and freshwater fishing — tarpon fishing being his favorite. He’s also a passionate sports fan and can always be found cheering on THE Ohio State Football Team and The Cleveland Browns.
President
Chris Degueldre
Executive Vice President
Chris joined Explain My Benefits (EMB) in 2009 as a managing partner and owner, with a focus on integrating Benefits Administration and Online Enrollment technology solutions within the existing suite of benefit communication services. He has played an integral role in shaping the client facing suite of solutions and developing the internal resources leveraged to deliver across nearly every industry. One of Chris’s greatest accomplishments is the talented, motivated team of professionals who have been strategically assembled — working together each day to serve clients and achieve EMB goals.
Chris earned his Bachelor of Science in Finance and Master of Science in Decision and Information Sciences from the University of Florida. He began his career working with a Japanese owned consulting company, Y.M.P.-international, where he implemented and integrated Enterprise Resource Planning (ERP) software systems across the United States. During this time, he achieved his ISO 9001:2000 Quality Management System accreditation and obtained ISO 9001 certification for an Orlando based manufacturing company.
Outside of EMB, Chris prioritizes time with his wife, two children and extended family. As a blended household of Florida Gators and UCF Knights fans, the family cheers on their teams through thick and thin. Much of his free time is spent in the gym or on the fields with his kids, and when time allows, Chris can be found fishing the waters of the Gulf or Atlantic in pursuit of the next big catch.
Executive Vice President
James Dawson
Senior Vice President
As Senior Vice President, James works closely with EMB’s broker partners, insurance carriers, and clients around the country, helping to cultivate and grow the EMB brand on a national level. He enjoys learning about the unique challenges organizations face with benefits technology and open enrollment logistics, then collaborating to develop solutions that drive greater efficiency and long-term success.
James began his insurance career in 2004 with Unum and went on to also hold roles at Lincoln Financial Group and Boston Mutual before joining the EMB team in 2019. His diverse industry experience allows him to bring a well-rounded perspective to client relationships and strategic partnerships.
Originally from Portland, Maine, James graduated from Boston College where he was a member of the Eagles Baseball Team. He now resides in Tampa, Florida with his wife and two young children — an enthusiastic Tampa Bay Buccaneers family! Outside of the office, James enjoys coaching his children’s baseball and football teams and is actively involved in his church, where he teaches first-grade Religious Education.
Senior Vice President
Meet Our Leadership Team
Roslyn Hines
Vice President of Account Management
A Favorite Part of Working at EMB:
I truly enjoy working at EMB because of the strong support I receive from both my team members and our leadership. The collaborative spirit within the team motivates me to perform my best. Collaboration, trust, and open communication make every challenge easier to tackle and every success more meaningful.
Enjoyment Outside the Office:
Every Wednesday after work, I meet up with friends for trivia. It’s fun to get some answers right but even more fun laughing at all the wrong answers. I also love to travel, especially my annual cruise for spring break. It’s a great way to celebrate the completion of another Open Enrollment and IRS ACA tax season.
Favorite Sports Team(s):
Philadelphia Eagles
Joe Mathein
Vice President of EDI
A Favorite Part of Working at EMB:
A healthy, supportive, and inclusive culture makes daily work enjoyable and motivating.
Enjoyment Outside the Office:
Tennis, Golf, College Football, Music
Favorite Sports Team(s):
University of Michigan, UCF, and Cincinnati Bengals
Brian Jacobs
Vice President of Operations
A Favorite Part of Working at EMB:
It’s that everyone cares. Being around people who care and want to do good for others is so important.
Enjoyment Outside the Office:
It’s simple — Creating memories with my family and friends.
Favorite Sports Team(s):
Chicago Bears and Chicago White Sox
Jackie Thomas
Office Executive
A Favorite Part of Working at EMB:
My co-workers. It’s nice to enjoy and like the people you work with. EMB has always been like a family.
Enjoyment Outside the Office:
I always love spending time with my family. I also enjoy drawing, the arts, and traveling.
Favorite Sports Team(s):
New York Yankees!
David Roque
Director of Operations
A Favorite Part of Working at EMB:
Working alongside Brian Jacobs and my Operations colleagues.
Enjoyment Outside the Office:
Music… I play the bass, but most importantly, I love spending time with my family.
Favorite Sports Team(s):
Philadelphia Eagles – Go Birds!
Stephenie Froemmling
Director of Account Management
A Favorite Part of Working at EMB:
All the wonderful people I work with day in and day out.
Enjoyment Outside the Office:
Family time is my favorite time and screaming on roller coasters is always the best!
Favorite Sports Team(s):
Oviedo Trash Pandas – “t-ball!”
Jeaniel Rodriguez
Director of Implementations
A Favorite Part of Working at EMB:
I enjoy the relationships we’ve created over the years, working alongside some great people.
Enjoyment Outside the Office:
I love spending time with my kids and dogs, taking the boat out, and enjoying the beach. Visiting theme parks and riding roller coasters is one of my all-time favorites as well.
Favorite Sports Team(s):
Formula 1 Racing (Lewis Hamilton, the G.O.A.T is my favorite Driver)
Abby Christensen
Director of EDI
A Favorite Part of Working at EMB:
Working alongside my teammates to tackle and solve the difficult EDI problems. Solving the seemly impossible challenges fills me with a sense of accomplishment but then seeing teammates build on that guidance or scenario and apply/adapt that knowledge to future challenges is very rewarding.
Enjoyment Outside the Office:
It’s simple, I enjoy anything I do if I am spending time with my family. We love traveling, spending time at the theme parks, on the water or fun home days relaxing in the pool.
Favorite Sports Team(s):
My daughter’s Competition Dance team is always fun and exciting to watch! Orlando City, Orlando Pride, UCF, Tampa Bay Bucs, Tampa Bay Rays.
Pillars of Success
At EMB, our employees uphold the highest standards of service and consistently exceed the expectations of our broker partners and clients. Discover the core values that guide and motivate every EMB employee to succeed.

Our team members are committed to ongoing learning and development, empowering our broker partners and clients with innovative strategies, streamlined processes and advanced technology solutions.

At EMB, leadership means taking pride in our work while we inspire and support others. We lead by example and foster a culture of collaboration and accountability with our broker partners and clients, resulting in successful outcomes for all parties.

EMB team members recognize the power of a unified team effort that drives stronger outcomes and collective success.

EMB team members bring positivity and professionalism to every interaction, ensuring you feel supported, valued and confident in our partnership.