Our Team

Hi, my name is Joe Donovan and I am the Chief Executive Officer at The Difference Card.  

I ended up in the Insurance Industry because, like many people graduating college, I needed a job. Back then, UnitedHealthcare had a training program called “group school” and I was lucky enough to get accepted. Little did I know that once you start in the insurance business it’s very hard to ever leave.  

I was drawn to The Difference Card because of the innovative nature of the company. Since its inception, The Difference Card has been an industry leader in designing creative funding strategies to achieve savings for employers and their employees.  

My favorite part of the job is the people I get to work with. Both my Difference Card Teammates and what I view as the most forward-thinking Brokers within the brokerage community.   

My proudest accomplishment is playing a role in creating our Difference Guarantee Savings Solution. Since we first rolled this product out in 2018, it has helped organizations across the country save hundreds of millions of dollars.  I am motivated by competition – I love to win and I believe strongly that building a winning culture is important.   

Before I was a Difference Card Difference Maker I was born in Philadelphia, PA, but grew up in Westchester County, NY.  I attended Syracuse University and currently reside in Armonk, NY with my family. 

Here are three fun facts you might not know about me:

1. I have twin boys

2. I traveled to Ireland to compete in a boxing match as part of the NYPD Boxing Team vs. The Garda.

3. I have an irrational aversion to tuna fish.

Rosa Garcia Rinder is the Chief Operating Officer and joined The Difference Card in 2020.

Rosa joined The Difference Card because they are an organization that is innovative, diverse and helps employers save money on insurance while retaining high level of benefits for their employees. Rosa’s main objectives at The Difference Card are to deliver an amazing experience for our client partners, grow so that our teams can share in that, and be a great place to work.

Rosa started her career in this industry at Choice Strategies in 2005. Rosa joined the Choice team as a member service representative and employee number 20; and within a few years rose to Director of Operations. As Director of Operations, Rosa was responsible for a team of over 100 employees and functions including, Member Services, Claims, Client Services and Implementation and Enrollment functions.

In 2012, Choice was acquired by WageWorks and Rosa stayed on for another two years, working to bring the Choice team into the WageWorks Family. In 2015, Rosa joined Alegeus where she held roles including Director Solution Architecture and Director of Strategic Accounts. At Alegeus, Rosa worked with dozens of administrators and some of the largest carriers in the United States, helping bring to market their CDH solution.

Rosa is originally from Queens, and grew up between there (Go Sunnyside!) and Madrid, Spain. Rosa went to college in Vermont, graduating from the University of Vermont. She loved it so much, she stayed in the Green Mountain State for 20 years- hiking, skiing, swimming! Currently, Rosa resides in Arlington, Massachusetts where she is raising a wild and fierce daughter, Ava Luna (yes, adaptation of Eva Luna from the book!). Rosa loves to learn, loves to run, loves to travel, loves her nieces and nephews and spending as much time with family and friends.

Hi, my name is Chris Calderone and I am the Chief Revenue Officer at the Difference Card. I got my start in the insurance business a little differently than most people. The head of maintenance at the school I worked in was family friends with an Aetna Sales Director. That Aetna contact was married to my 3rd grade teacher, and we had gone to the same University, so we had a few connections. I enrolled in the Aetna Group School to learn the insurance business. I was drawn to The Difference Card because after working for Aetna and Anthem BCBS, I saw first-hand the excess margin on the insurance carrier side.

The Difference Card was disrupting the middle market by giving back premium to the employer and providing great benefits for employees. My favorite part about working for The Difference Card is the commitment to the entrepreneurial spirit. Our team is constantly improving processes to make the customer experience outstanding. My proudest accomplishment is helping one of our large non-profit customers to save $5 million off their health insurance policy in their first year with The Difference Card. I am motivated by our customers. I love to learn about our customer’s business and help them to solve complex insurance problems.

Before I was a Difference Card Difference Maker

I was born in New York, NY and I currently reside in Mamoroneck, NY with my wife Erica, two children, Stella and Cooper, and our wire-haired Dachshund, Rigatoni. I attended the University of Notre Dame and was the captain of the club boxing team. Every year we would host an annual charity boxing tournament called the Bengal Bouts with all proceeds funding a mission in Bangladesh. My first job was a cleaner in the New York City public schools. I can still give any floor a great shine! Growing up, my favorite movie was The Mighty Ducks and I played on a travel street hockey team.

Here are three fun facts you might not know about me:
1. My favorite sports team is The University of Notre Dame. Go Fighting Irish!
2. If I could travel anywhere in the world I would travel to Italy. There are so many great parts of Italy, and the food is incredible.
3. Outside of work I love to swim and paddle board. I love being around the water!

Since joining The Difference Card, as the Chief Technology Officer, Dan has focused on optimizing the use of technology to better serve our broker and employer clients. Previously, Dan has spent over 20 years working in the healthcare technology space focusing on sales automation and analytics.

He architected and managed the development of the HealthConnect platform, which was the largest provider of small group health quotes in the US.

Hi, my name is Ashley Dube, and I am the Senior Director of East Markets at The Difference Card. I ended up working in the insurance business because I completed an internship with Northwestern Mutual when I was in college. Initially, I was focused on personal financial planning, but then received an opportunity to work in the Employee Benefits Department. The rest is history.

I was drawn to The Difference Card because I love being able to offer a unique health insurance funding product to companies who are struggling to contain costs or looking to improve benefits. My favorite part about working for The Difference Card is working with a diverse and very talented team. My proudest accomplishment is how the New England Market has grown over the past seven years. I am motivated by competition. I am an extremely competitive person. I always strive to finish first in any aspect of my life.

Before I was a Difference Card Difference Maker

I was born in Providence, RI and I currently reside in Cumberland, RI with my husband, Steve, and our two children- Brady, who is 6 and loves sports and Brooklyn, who is 4 and loves unicorns and princesses. I graduated from the University of Rhode Island with a major in Business Management & Marketing. I loved living off campus (“down the line”) in a beautiful beach house with an ocean view. This is when I fell in love with the cute beach town of Narragansett, RI. Growing up my first job was as a Food Runner at a local restaurant when I was 15.

Here are three fun facts you might not know about me:
1. My idea of a perfect day is working out in the morning, hitting the beach on an 80-degree day, followed by happy hour with a cold drink in hand.
2. My most useless talent is that I can easily memorize license plates.
3. If I could have dinner with any person dead or alive it would have to be Kenny Chesney!

Hi, my name is Stephanie McNellis, and I am the Director of Client Retention at the Difference Card. I ended up working in the insurance business by chance.  When I first interviewed at The Difference Card, I had a great feeling about the company and the people, It turns out I was right. 15 years later I know I made a great decision! My favorite part about working for The Difference Card is the savings we achieve every year for our clients. I am fortunate to work with incredibly talented people who consistently challenge me to learn and grow. My proudest accomplishment has been leading the Client Success team. It is a privilege to be part of a team who cares so deeply for our clients. I am proud of the passion I see every day from our team and the results they have been able to achieve. My daughters are what motivate me every day; I try to be the best version of myself for them.  

Before I was a Difference Card Difference Maker

I was born in Sleepy Hollow, NY and currently reside in Buchanan, NY with my husband, Brian: our two daughters, Madison 7 and Aubrey 4. I attended the State University of New York at Oneonta. One of my first jobs in high school was waitressing at Friendly’s, I learned very quickly how bad my balance was while trying to hold more than one milkshake.  That moment didn’t end well but I learned many foundational skills from my short time there that I carry with me today.  Growing up I spent hours outside, riding bikes with friends, and waiting impatiently until it was dark enough to play flashlight tag around the neighborhood.  

Here are three fun facts you might not know about me:  

1. Outside of work in the warmer weather, I love to be on the water, going for boat rides or swimming in the pool.

2. I love any true crime podcast or documentary.

3. As hard as it is to admit, I am a NY Jets fan. Sunday’s in the fall are reserved for tailgating and cheering them on, J-E-T-S, Jets, Jets, Jets!

Hi, my name is Terry L. Robinson and I am the Manager of Client Success for the East Region at the Difference Card. I ended up working in the insurance business through a contact. I was working as a STEM teacher for the NYC Department of Education and my program funding was cut from the budget. An employee of the Difference Card shared an opportunity with me, and I went for it. I was drawn to The Difference Card because it was different than anything I had heard of. Health insurance was not particularly attractive to me, I thought it was complicated and I wasn’t sure about it. I believed The Difference Card could change that perception for those like me. My favorite part about working for The Difference Card is Creating solutions. There’s always an issue to solve for. My proudest accomplishment is Becoming the youngest black male leader at the organization and I am motivated by my family.  

Before I was a Difference Card Difference Maker  

I was born in Hampton, Virginia and I currently reside in New York, NY with my wife and three children. I attended City College of New York and growing up my first job was as a Docent at Hudson River Museum.  

Here are three fun facts you might not know about me:  

1. My idea of a perfect day is Sleeping in until about 11am, shopping at the mall with my family and a great dinner and dessert to end the day.  

2. My favorite sports team is the Los Angeles Lakers.  

3. If I could travel to anywhere in the world, it would be Israel.  

Hi, my name is Taylor Britt and I am the Senior Director of Marketing + Sales Media at the Difference Card. I was drawn to The Difference Card because I loved the idea of joining a team that is working to solve the problem of the rising cost of healthcare. My favorite part about working for The Difference Card is the people- I think some of the funniest, hardworking, creative & dedicated individuals work for The Difference Card! My proudest accomplishment is building a successful and growing Marketing Department. I am motivated every day by the good work that we do.

Before I was a Difference Card Difference Maker

I was born in Chattanooga, TN and I currently reside in Nashville, TN with my husband, 2 young children and our dog Nola, a 13-year-old chocolate lab. I attended Middle Tennessee State University (MTSU) and graduated with a degree in Public Relations and Marketing. My first job was at Cracker Barrel where I worked as a server to pay my way through college. I can still recite the daily specials! I have many fond memories of growing up, but my favorite is of riding bikes at my grandmother’s house. When I was little, we would ride “big wheel” trikes down a giant grassy hill in the backyard at breakneck speeds.

Here are three fun facts you might not know about me:
1. My idea of a perfect day is a whole day spent on the beach from sunrise to sunset. I want to swim in the ocean, read a book, take a nap and watch the sunset while never leaving the beach.
2. As a Nashville Native, the Tennessee Titans are obviously my favorite sports team! #titanup!
3. If I could travel anywhere in the world, I would want to visit the Greek Islands. Santorini is on my bucket list!