Jennifer E. Shirkey

Jennifer E. Shirkey


Jennifer Shirkey concentrates her practice in estate planning, employee benefits, tax, and business law. She assists families and individuals with their trust and estate needs daily and serves as an Assistant Commissioner of Accounts for Harrisonburg & Rockingham County. In addition, she helps business, non-profit and governmental employers of all sizes navigate their employee benefit plans through the Internal Revenue Code and ERISA. She has particular expertise in the sophisticated area of employee stock ownership plans (ESOPs) and other equity compensation programs.

Jennifer advises on the tax and business aspects of for-profit and non-profit entity startups, as well as their ongoing operations and mergers and acquisitions. She has worked extensively with health care providers and educational institutions on benefits and tax compliance issues. In working with clients, she applies her technical legal expertise to give practical counsel and develop creative strategies to estate planning, employee benefits, and general business challenges. She is a frequent public speaker on tax issues.

Jennifer lives in Harrisonburg with her husband and three children.


  • Developed wealth transfer plans for many business owners and other individuals with an emphasis on tax, succession and philanthropic issues
  • Guided families through the estate and trust administration process and resolved conflicts
  • Counseled institutional fiduciaries on a wide variety of estate and trust matters
  • Drafted and reviewed for ERISA and tax compliance scores of retirement plans, including main plan documents, summary plan descriptions, adopting resolutions, trusts, QDROs, administrative policies and forms, annual reporting and disclosure issues, and 404(c) participant-directed investing and other fiduciary matters including 401(k), profit sharing, 403(b), 457, defined benefit and ESOP plans
  • Assisted numerous for-profit and non-profit organizations with executive deferred compensation matters, including SERPs, stock options and appreciation rights, phantom stock, ineligible 457(f) plans, and split dollar life insurance as well as funding mechanisms such as Rabbi trusts and avoiding penalties under the 409A rules
  • Designed, implemented and updated all types of welfare and fringe benefit plans, including Section 125 cafeteria/flexible spending plans, insured and self-insured health plans, short- and long-term disability plans, life insurance benefits, tuition assistance plans, dependent care benefits and employee assistance programs
  • Developed COBRA and HIPAA compliance forms and procedures for many insured and self-funded health plans
  • Counseled clients regarding remedial strategies for non-compliant benefit plans, including use of the EPCRS, DFVC and VFC programs
  • Prepared organizational documents and obtained tax-exempt status determination letters for 501(c)(3) and other non-profit entities and advised them regarding ongoing concerns such as directors’ duties and liabilities, annual reporting and UBIT issues
  • Worked with large and small employers across a range of industries - specifically including health care, education, agriculture and hospitality -to analyze their obligations and implement compliance solutions under the Affordable Care Act's 4980H "play or pay" and other mandates
Appointments & Other Experience
  • Assistant Commissioner of Accounts for the Rockingham County Circuit Court, 2013-Present
  • Law Clerk to the Honorable H. Emory Widener, Jr., US Court of Appeals for the Fourth Circuit, 1996-1997


  • Virginia
  • U.S. Court of Appeals for the Fourth Circuit
  • U.S. District Court for the Western District of Virginia


  • Fellow, The American College of Trust and Estate Counsel (ACTEC)
  • Fellow, American Bar Foundation
  • "Legal Elite," Taxes/Estates/Trusts, Virginia Business, 2020
  • The Best Lawyers in America®, Employee Benefits (ERISA) Law, 2010- 2022 (Copyright by Woodward/White, Inc., of Aiken, SC)
  • “Virginia Rising Stars,” Tax, Super Lawyers, Thomson Reuters, 2007-2009 and 2011-2012
  • Law Clerk to the Honorable H. Emory Widener, Jr., US Court of Appeals for the Fourth Circuit 1996-97


Professional Involvement

  • Virginia Bar Association
    • Wills, Trusts & Estates Section
    • Council and Legislative Committee Member
  • Virginia State Bar
    • Trust and Estates Section
    • Board of Governors, Past Chair
  • American Bar Association
    • Joint Committee on Employee Benefits
  • Harrisonburg-Rockingham Bar Association
    • Probate Section Co-Chair
    • Past Secretary

Fellow The American College of Trust and Estate Counsel

Community Involvement

  • JMU Foundation
    • Board Member
  • Wildlife Center of Virginia Foundation
    • Board Member
  • Harrisonburg Rotary Club
    • Past President
  • The Community Foundation of Harrisonburg and Rockingham County
    • Past Chair
  • Harrisonburg-Rockingham Chamber of Commerce
    • Past Board Member
Practice Areas Education

Washington and Lee University School of Law
Lexington, Virginia
J.D., Summa Cum Laude, 1996

Order of the Coif
Washington and Lee University Law Review, Editorial Board

James Madison University
Harrisonburg, Virginia
B.A., Summa Cum Laude, with Distinction, English, 1993

Highlighted Recognitions

Fellow The American College of Trust and Estate Counsel
Best Lawyers Badge