The difference card welcomes people graphic

The Difference Card Welcomes New Leaders for Technology and Risk Management

January 13, 2026

Joseph Donovan

Chief Revenue Officer

Joseph Donovan is the Chief Executive Officer for The Difference Card. Joseph began his career in employee benefits with United Healthcare in 2004. Shortly after that, he joined The Difference Card in 2008 as one of the founding Senior Sales Consultants. After a tenured career in sales serving as EVP of Sales and Chief Revenue Officer with The Difference Card, Joseph was appointed as CEO in 2022. During his time as CEO, Joesph has seen necessity of providing better health benefits at a better price for fully-insured employers while championing the employee experience.

Greenwich, CT – The Difference Card, a leading provider of cost-effective health insurance solutions, announced today that two new leaders, Richard Perrin and Matthew Hegarty, will be joining the team to manage the Technology and Underwriting Departments.

Richard Perrin has been named Chief Technology Officer at The Difference Card, bringing more than 15 years of experience leading technology innovation and scaling high-performance engineering teams. Most recently as CTO at Remodel Health, Richard has a proven track record of driving digital transformation and building advanced software platforms.

His leadership and technical expertise will play a pivotal role in advancing The Difference Card’s technology strategy and delivering cutting-edge solutions to clients. Richard holds an MBA from Syracuse University and a B.S. in Business Computer Information Systems from Indiana University.

Matthew Hegarty joins The Difference Card as Vice President of Underwriting, bringing more than a decade of expertise in risk analysis and pricing strategy. With a proven track record of risk management at Granular Insurance, Aetna and GeoBlue, Matthew has driven innovative underwriting solutions and actuarial insights that deliver measurable results.

His strong analytical background, combined with leadership experience, positions him to advance The Difference Card’s mission of delivering innovative solutions tailored to the unique needs of small and mid-sized businesses. Matthew holds a B.S. in Mathematics with a concentration in Actuarial Science from West Chester University of Pennsylvania.

“I am thrilled to welcome Rich and Matt to our team. As we continue on our mission to make healthcare more affordable, technology and risk management will be critical drivers of success. Their expertise and insight will help accelerate innovation and contribute significantly to our growth in the years ahead.”

– Joseph Donovan, Chief Executive Officer of The Difference Card

To learn more about The Difference Card, visit DifferenceCard.com.

Key Takeaways

The Difference Card (Greenwich, CT), a leading provider of cost-effective health insurance solutions, announced two new leaders to manage its Technology and Underwriting departments.
Richard Perrin has been named Chief Technology Officer; he brings more than 15 years of technology leadership, was most recently CTO at Remodel Health, and holds an MBA from Syracuse University and a B.S. in Business Computer Information Systems from Indiana University.
Matthew Hegarty joins as Vice President of Underwriting with over a decade of experience in risk analysis and pricing, having worked at Granular Insurance, Aetna, and GeoBlue; he holds a B.S. in Mathematics with a concentration in Actuarial Science from West Chester University of Pennsylvania.
CEO Joseph Donovan stated that technology and risk management will be critical drivers of success as the company continues its mission to make healthcare more affordable.
For more information, visit the company's website: DifferenceCard.com.