Jason Sheffield, JD

Director & Managing Attorney, Health & Benefits Compliance, Willis Towers Watson
Jason Sheffield
Jason joined Willis Towers Watson in 2013 as a senior consultant for the Health and Group Benefits Compliance Practice. He supports the Health and Group Benefits Practice by providing assistance and technical expertise to Willis Towers Watson clients located primarily in the western region.

Jason has experience in a broad range of employee benefit matters respecting both retirement and welfare plans. He has worked with clients of all sizes to develop, implement and administer qualified and non-qualified plans. Prior to joining Willis Towers Watson, Jason worked with a national legal practice advising clients on a range of benefit and tax issues. He has represented corporate, institutional and individual clients before several administrative agencies, including the Department of Labor, Internal Revenue Service and the Centers for Medicare & Medicaid Services.

Prior to working as a benefits consultant, Jason worked as a litigation consultant, advising on multi-district and complex litigation related to oversight and administration of ERISA-governed benefit plans. He has also worked as a lobbyist, researching the costs and benefits of alternative employee benefit and compensation designs and educating lawmakers and the public on specific issues such as expansion of domestic partner benefits, HIV/AIDS-related employment discrimination, and inclusion of transgender-inclusive employee benefits.
Jason received his J.D. from Western New England University School of Law and his B.A. from Georgia State University, magna cum laude. He has spent significant time as a lecturer and instructor on health and benefits issues.

Last year, Jason was a featured speaker at the Society of Human Resource Professionals’ (SHRM) 2018 National Conference & Expo where he spoke regarding recent agency rulemaking related to the administration of gender expression and gender identity in the workplace. Jason was also a guest presenter at the World at Work 2017 National Conference & Expo where he spoke regarding the advent and regulation of value-added benefits such as on-site clinics, telemedicine, and employer-sponsored well-being programs. In 2016, Jason was a guest speaker at the Employee Benefit Network’s (EBN) 2016 National Conference & Expo where he hosted a panel discussion on emerging employee benefits issues and moderated a large-scale total rewards group-based hypothetical exercise he designed titled The Ins and Outs of Plan Design & Administration.