Kara Maddalena

Kara Maddalena began her career in employee benefits at the U.S. Department of Labor's Employee Benefits Security Administration (EBSA). At EBSA, she investigated and assisted in litigation involving complex ERISA violations and completed a detail at the agency's national office, where she helped implement and advance the agency's highest enforcement priorities. She subsequently transitioned to private practice, where she advises employers, plan sponsors, fiduciaries, trustees, investment managers, and employee benefit service providers on a broad range of ERISA, employee benefits, and executive compensation matters.

Kara assists clients with the full spectrum of employee benefits issues affecting retirement, health and welfare, and executive compensation programs. Her experience includes advising on qualified retirement plans, including 401(k), 403(b), governmental and tax-exempt 457(b), and defined benefit pension plans, as well as nonqualified deferred compensation arrangements, health and welfare plans, disability benefit programs, and cafeteria plans. She counsels clients on plan administration and compliance, ERISA litigation, and employee benefits considerations arising in mergers, acquisitions, and other corporate transactions.

Clients frequently turn to Kara to address their most complex employee benefits challenges. She is particularly experienced in advising on fiduciary governance, prohibited transaction analyses, controlled group and affiliated service group determinations, withdrawal liability matters, ACA, HIPAA, COBRA, and executive compensation issues. She has significant experience with self-funded welfare plans and regularly advises on disability benefit claims, ERISA claims and appeals procedures, and related administrative and compliance matters. Drawing on her experience in both government and private practice, she represents clients in Department of Labor and Internal Revenue Service audits, investigations, and enforcement proceedings. Kara also advises clients on emerging issues affecting employee benefit plans and their service providers, including pharmacy benefit manager regulation and the use of AI in employee benefit plan administration and claims-processing functions.

Known for her pragmatic and business-oriented approach, Kara works closely with clients to translate complex legal and regulatory requirements into practical strategies that support innovation, mitigate risk, and further organizational objectives.