Founder & President
Ari Gross founded Columbia Group in 2005 with a vision to bring a smarter, more personal touch to the world of employee benefits. Columbia Group quickly grew into one of the region’s fastest-growing insurance agencies, serving businesses and individuals across Maryland/DC and beyond.
With a knack for corporate analytics and a deep understanding of human resource structures, Ari helps clients find solutions that are as strategic as they are practical. His insights have landed him on Fox 45 News multiple times, where he’s shared his expertise on the Affordable Care Act and the ever-changing benefits landscape.
A proud University of Maryland alum (Go Terps!), Ari studied finance and business administration before launching his career. He now lives in Baltimore with his family, where he’s just as passionate about giving back as he is about business, serving on the boards of several local nonprofits and staying active in community charities.
When he’s not in the office, you’ll likely find Ari on the golf course or coaching his sons’ Little League baseball and football teams. Whether it’s on the field or in the boardroom, he brings the same mix of energy, focus, and enthusiasm to everything he does.
Director of Operations / Benefits Specialist
A Baltimore native, Dena ventured to Manhattan for college before returning home to raise her family and build her career. At Columbia Group, she wears many hats—working with both large and small group clients to select, implement, and manage their insurance benefits, while also playing a key role in the company’s internal finance, operations, and efficiency initiatives.
A certified QuickBooks ProAdvisor, Dena has a true love for data and the satisfaction that comes from reconciling information (yes, she admits it’s a little strange—but she owns it!). Known for her thoughtful client relationships, Dena ensures that every client knows exactly who to turn to when they have questions. She thrives in the fast-paced, ever-changing world of employee benefits and is always finding smarter, more efficient ways to get things done.
When she’s not diving into numbers or brainstorming process improvements, Dena enjoys baking, reading, taking long walks, and, of course, her daily coffee.
Commercial Markets Manager
Born and raised in Baltimore, Hannah brings energy, expertise, and a “get it done” attitude to everything she does. As Columbia Group’s commercial markets manager, she works closely with business owners and their HR teams to strategize and facilitate employee benefits with precision and care. Hannah thrives in a collaborative environment where teamwork turns great ideas into results.
Outside of work, Hannah channels her creativity into baking and giving back to the community. She volunteers with The Associated: Jewish Federation of Baltimore and was honored with the Zelda Miller Award in 2024 for her outstanding service.
Her perfect morning? An early Peloton ride, a good journaling session, and a well-earned Starbucks coffee in hand.
Hannah enjoys spending quality time with her family and friends.
Individual Markets Director / Benefits Specialist
Originally from Buffalo, New York, Faith has called Baltimore home for nearly two decades. At Columbia Group, she specializes in helping small groups and individual clients find the benefits that fit them best, because she knows that one size never fits all.
Faith has a gift for making the complex world of insurance feel simple and approachable, and her clients appreciate her caring, down-to-earth style.
When she’s not helping clients, you’ll find Faith enjoying a good book, great music, and quality time with her children, grandchildren, and friends. She’s a proud morning person—as long as there’s coffee involved!
Individual Benefits & Marketing Specialist
Toby was born and raised in Baltimore, Maryland, as the oldest of four siblings. She and her husband currently live locally and are enjoying raising their own beautiful family. Artistic and detail-oriented, she incorporates both creativity and precision into her role at Columbia Group, where she works with individual health and life insurance clients. Toby also puts her artistic ability to good use by designing marketing materials and creating group health benefits guides that are both comprehensible and visually pleasing.
As an effective communicator with a patient and compassionate approach, Toby enjoys helping clients understand the intricacies of insurance benefits. Her ability to blend creativity with clarity makes her an invaluable resource for her clients and colleagues.
Outside of the office, Toby’s artistic side shines through her passion for interior design and decorating. In her spare time, you can find her perusing through the aisles of HomeGoods or planning elaborate birthday parties for her kids which is her favorite creative outlet.
Group Benefits Account Manager
Born in Philadelphia and raised in Baltimore since age 11, Shawna brings warmth, precision, and a love of organization to everything she does. As a Group Benefits Account Manager at Columbia Group, she oversees the management and renewal of small group health insurance accounts—coordinating plan options and renewals, supporting account executives and clients with benefit strategy and compliance, and ensuring every new group has a smooth onboarding experience.
Shawna takes real pride in keeping things running seamlessly behind the scenes. She thrives on managing multiple accounts efficiently while helping clients navigate their benefits with confidence and ease. Her clients and colleagues alike appreciate her reliability, attention to detail, and calm professionalism.
A self-proclaimed morning person (especially when the air turns crisp in fall), Shawna enjoys spending her downtime with family and friends—and putting her organizing skills to good use at home.
From plan selections to enrollment and implementation, we manage every detail with efficiency to guarantee a seamless process and a positive experience for both employers and employees.
