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Hillary M. Sizer

Associate   |   Chicago

Hillary is an associate at Ogletree Deakins whose practice covers all types of employee benefit plans, including 401(k), defined benefit, deferred compensation, governmental, welfare, multiple employer, and multiemployer plans. She assists clients in all aspects of employee benefits including Internal Revenue Service (IRS) filings, self-corrections, Voluntary Correction Program applications, IRS and Department of Labor (DOL) audits, service provider agreements, reviewing marketing materials, plan corrections, and fiduciary and prohibited transaction issues. She also advises on all tax-related aspects of employee benefits including the taxation of settlement awards, restorative payments, taxation and reporting of fringe benefits and welfare benefits, and employment taxes. In addition, Hillary counsels clients on various employee benefits matters in relation to corporate mergers, sales, and acquisitions. Her practice also includes a focus on data privacy and cybersecurity issues.

Hillary’s extensive experience with health and welfare plans covers the full range of federal and state laws that impact the administration of self-funded and fully insured health & welfare benefit plans, Section 125 cafeteria plans, health savings accounts (HSAs), health reimbursement arrangements (HRAs), flexible spending accounts (FSAs), voluntary employees’ beneficiary associations (VEBAs), wellness programs, expatriate coverage, fringe benefits, captive insurance arrangements, and other employee benefit arrangements. She has provided advice on compliance with the Employee Retirement Income Security Act (ERISA), the Affordable Care Act (ACA), the Consolidated Omnibus Budget Reconciliation Act (COBRA), the Health Insurance Portability and Accountability Act (HIPAA), the Mental Health Parity and Addiction Equity Act (MHPAEA), and tax laws. She also advises clients on compliance issues related to wellness programs under HIPAA, the Americans with Disability Act (ADA), and the Genetic Information Nondiscrimination Act (GINA). She has drafted plan documents, summary plan descriptions, and benefit claim responses, and successfully defended her clients in plan audits, Employer Shared Responsibility Payment assessments, and multiemployer payroll audits. Recently, Hillary has been advising clients on rapidly evolving areas in federal civil rights law and state abortion and transgender laws.

Before joining Ogletree Deakins, Hillary completed an externship at the Oregon State Tax Court and graduated, with distinction, from Georgetown University Law Center where she earned a Master of Laws (LL.M.) in Taxation and an Employee Benefits Certificate. She received her B.A., cum laude, in Philosophy from Colorado State University.

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