Thomas Cryan

Thomas Cryan is a partner in our Employee Benefits & Executive Compensation and Tax practice groups in Washington, D.C. He advises Fortune 100 companies and large employers on executive compensation, fringe benefits, employment tax, and related compliance and reporting matters. With over 25 years of experience at the intersection of tax, benefits, and workforce strategy, he helps clients navigate complex regulatory frameworks and align compensation programs with broader business goals.

Tom’s work focuses on advising legal, tax, and HR leadership on the tax treatment and reporting of a wide range of compensation and benefit arrangements; from stock-based awards and deferred compensation under Internal Revenue Code Section 409A to fringe benefits such as travel and personal use of corporate aircraft, medical and wellness benefits, qualified employee discounts, and settlement and golden parachute payments. His guidance helps employers structure programs that are both competitive and compliant with federal tax law.

In addition to executive compensation counseling, Tom advises on employment tax issues, including FICA and wage withholding considerations, deduction limitations under Code Section 162(m), Remote Worker and multi-state tax issues, Affordable Care Act compliance, and the tax implications of the Employee Retention Credit. He also represents employers in employment tax and compensation audits before the IRS and state authorities, drawing on extensive experience with IRS administrative practice and procedure.

Tom is recognized for translating complex tax and benefits rules into clear business guidance. He is a frequent speaker for industry groups including the Tax Executives Institute, the American Benefits Council, and the American Bar Association, and has been interviewed by major media outlets on executive compensation and benefits trends. He co-authored the authoritative Tax Management Portfolio on golden parachutes and has been recognized in The Best Lawyers in America for Employee Benefits (ERISA) Law.

Clients value Tom’s practical perspective and his ability to partner with in-house counsel, tax, and HR teams to solve intricate compensation and tax challenges that arise in today’s competitive talent and regulatory environment.

Representative Experience

• Counseled a large biotechnology company on the application of IRS rules affecting spousal travel, personal use of corporate aircraft, mixed business and personal flights, and deduction disallowance for entertainment use of corporate aircraft.
• Advised an employer with a highly mobile workforce in developing internal procedures for the proper taxation of travel reimbursements and per diem payments.
• Successfully represented a Fortune 100 company in IRS Appeals proceedings concerning the tax treatment of relocation reimbursements and corporate aircraft use, resulting in full concession by the IRS.
• Participated in and supported a Fortune 100 company’s engagement with the U.S. Department of the Treasury regarding the taxation of employer wellness programs.
• Assisted an employer on the taxation of an on-site cafeteria and the tax treatment of conferences and conventions.
• Advised and supported a large financial institution in restructuring payroll practices to avoid FICA restart provisions, reduce employment tax exposure, and address internal payroll tax administration concerns.
• Defended a large manufacturing company in challenging an employment tax deposit penalty, achieving abatement at the IRS Appeals level.
• Handled the defense of a large multi-state employer in a state income tax audit involving non-resident wage withholding.
• Assisted multiple clients in securing more than a dozen private letter rulings under Internal Revenue Code Section 162(m).
• Conducted analysis for an acquisition target company regarding potential Internal Revenue Code Section 280G implications of compensation plans and employment agreements.