Leadership Team

Todd Baxter

Chief Executive Officer

Todd joined Benefytt as Chief Executive Officer (CEO) in June of 2022, bringing decades of experience leading global customer service organizations for marquee companies. 

Previously, Todd oversaw the technological transformation and integration of HireRight as its EVP and Chief Service Officer. Todd also served as President of the Healthcare division and COO for two of the world’s largest Business Process Outsourcing companies and held leadership roles with global Fortune companies in the telecommunications, financial services, and healthcare sectors. Todd earned an MBA with an emphasis in Technology Management and a BBA in Finance. 

When not working, Todd enjoys spending time on, in, or around water with his family and friends. 

Mark Longaro


Mark Longaro serves as the President of Benefytt Technologies and is responsible for media placement across all marketing channels, oversight of all sales and distribution channels, as well as developing and nurturing agency partnerships.  

In his previous role, Mark was President and CMO of an insurance distributions and marketing company. In this role, he had a unique knowledge of identifying target audiences through direct response television, radio, print, mobile, and web campaigns and converting them into successful A&H and Medicare product enrollments. 

When not at work, Mark, is an avid fisherman who enjoys spending time on the water. He also loves spending time with his family and volunteering to coach his children’s sports teams.

Domenick C. DiCicco Jr., JD, MBA, CMAP, CCEP

Chief Legal Officer

Domenick serves as the Chief Legal Officer (CLO) for Benefytt Technologies and is responsible for the company’s legal and compliance services. 

In his previous roles, Domenick served in multiple General Counsel and Compliance leadership positions at Zurich Financial Services, AIG, and Cunningham Lindsey and Sedgwick. Domenick has served on multiple Boards of Directors including the ARC Association and the NJIT Business School and has held many higher education teaching roles. Domenick earned a Juris Doctor Degree from Delaware Law School, an MBA Degree from Penn State University, and a Master of Public Administration (Economic Development) Degree from the University of Pennsylvania and is also a Certified Merger and Acquisition Professional and a Certified Compliance and Ethics Professional. 

When not at work, Domenick enjoys building and playing guitars. 

Michael DeVries MBA

Chief Financial Officer

Michael DeVries serves as the Chief Financial Officer (CFO) for Benefytt Technologies and is responsible for the company’s financial affairs and planning. 

In his previous role, Michael was Vice President of Finance for Greenway Health, a leading healthcare IT company. At Greenway, Michael led the finance team in acquisitions, system implementations, strategy and operational effectiveness. Michael earned an MBA from The University of North Carolina, Kenan-Flagler Business School and a Bachelor of Arts in Economics from The University of Western Ontario. 

When not at work, Michael enjoys spending time with his wife and three daughters and traveling. 

Travis Conley

Chief Technology Officer

Travis serves as the Chief Technology Officer (CTO) for Benefytt Technologies, overseeing development, platforms, engineering and support teams. 

Prior to joining, Travis was the CTO of Swett and Crawford, the largest wholesale insurance brokerage in the country. He was responsible for technology platforms, support and development in North, Central and South American group companies. In addition, Travis spent several years as a CIO in regional banks. Travis earned a degree in Computer Engineering from Gainesville College and multiple certifications from industry organizations. 

Travis is an avid outdoorsman, spending time fishing and other watersports. He and his wife have 3 children and enjoy staying involved with their activities.

Kathryn Dawson

Chief Human Resources Officer

Kathryn Dawson serves as Chief Human Resources Officer (CHRO) for Benefytt Technologies and is responsible for the company’s talent and people strategy. 

In her previous role, Kathryn was Sr Vice President Human Resources for Experian, a multi-national consumer credit reporting company, where she partnered with executive leadership teams to design and build people solutions that aligned with key business priorities for a $2B business unit. Kathryn earned a BBA degree in Strategic Management from the University of North Texas. 

When not at work, Kathryn enjoys trying out new restaurants with friends and family. 

Tony Plampton

Chief Strategy Officer

Tony serves as Chief Strategy Officer (CSO) for Benefytt Technologies and also has responsibility for the Benefytt’s under sixty-five business unit P&L.  

Tony began his career at Lloyds of London with the last 30 years in the US working in the Life, Accident and Health markets. He founded the nation’s largest independent A&H focused reinsurance intermediary firm in 2001. Before joining Benefytt, Tony worked with the company as a consultant and intermediary partner. 

When not at work, Tony has a passion for skiing, golf and tennis. He is the immensely proud father of two grown daughters and spends as much time as he can with them. He is an avid reader, and a lover of food, wine and travel. 

Irene Kwak

Chief Growth Officer

Irene serves as the Chief Growth Officer (CGO) for Benefytt Technologies and is responsible for the company’s digital product strategy and marketing.  

In her previous role, Irene was the Chief Acquisition Officer at Sharecare, a health benefits platform, where she led a $400 million P&L for Fortune 500 employers, health plans, and government accounts. She also brings leadership experience in insurtech, fintech, media and publishing. Irene earned an MBA from Columbia University and a Bachelor of Science in Communication Studies from New York University.  

When not at work, Irene designs and makes porcelain jewelries for her small, local brand in Atlanta.

Jaclyn Hill

Chief Operations Officer

Jaclyn Hill serves as the Chief Operating Officer (COO) for Benefytt Technologies and is responsible for operational strategy and execution of the operating teams. 

In her prior roles, Jaclyn served in several senior leadership positions at Alegeus, a leader in consumer-driven healthcare.  While there, she built and managed member and employer services teams and led service delivery and implementation services, supporting the nation’s top health plans and third-party administrators.  Prior to her time at Alegeus, Jaclyn worked at Optum. Jaclyn earned a Bachelor of Science in Business Administration from the University of Central Florida. 

When not at work, Jaclyn enjoys camping and snorkeling in the Florida Keys with her husband and daughter. 

Tim Roach

SVP Carrier Relations

Tim serves as the Senior Vice President, Carrier Relations for Benefytt Technologies, and is responsible for forging and fostering profitable growth partnerships with all leading Medicare carriers. 

In his previous role, Tim was the Vice President of Medicare Marketing for Aetna/CVS Health, tripling the business to over 2 million members in seven years. Tim has years of experience in healthcare and consumer packaged goods companies including public, family, and private equity backed companies. Tim earned an MBA in Marketing and a Bachelor’s degree in Marketing and Finance from the University of Wisconsin. 

While not working, Tim travels the world with his wife Heidi, exploring new experiences and keeping track of their six children. Tim is a true cheese head from the great state of Wisconsin and an avid Green Bay Packers fan. 

Richard Hargrave

SVP Accident & Health (A&H)

Richard serves as Senior Vice President of Benefytt’s Accident & Health (A&H) division and is responsible for all facets of the A&H business. 

Prior to joining Benefytt in March 2021, Richard was Senior Vice President of the A&H reinsurance division at Risk Strategies Company. Prior to that role, Richard was a partner in an independent A&H reinsurance intermediary, Re-Solutions Intermediaries, which he helped found in 2001. Richard is an English Chartered Accountant and earned a Bachelor’s degree in Accounting and Economics from the University of Kent at Canterbury in England. 

Outside of work, Richard enjoys photographing birds and trying to keep the weeds down in his garden. 

Marcus Siegmund

Chief of Staff

Marcus serves as Chief of Staff for Benefytt Technologies, and helps to drive strategic initiatives across the organization. 

Prior to joining Benefytt, Marcus was an investment professional at Madison Dearborn Partners, where he was responsible for private equity due diligence and deal execution. Marcus earned a Bachelor of Arts from Princeton University. 

Marcus enjoys spending time with his wife, and appreciates both the outdoors and good urbanism. He is a former soccer player and an avid supporter of West Ham United. 

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