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Member

Cher E. Wynkoop

Cher E. Wynkoop

Credentials

Credentials

Education

  • LL.M., Capital University, Taxation, 1996
  • J.D., Capital University, 1994
  • B.S., United States Air Force Academy, 1989

Admissions - Bar

  • Virginia State Bar
  • Ohio State Bar
  • Pennsylvania State Bar

Involvement

  • Former Willcox Savage Policy (Executive) Committee
  • Chair, Willcox Savage Employee Benefits Practice
  • Former Chair, Willcox Savage Recruiting Committee

Designing Compliant Retirement and Executive Compensation Programs

Cher leads the firm’s Employee Benefits & Executive Compensation practice. She builds benefit programs that move business forward—and stand up to scrutiny. She designs, implements, and maintains complex benefit programs—from retirement and health & welfare plans to equity, deferred compensation, and executive employment and separation agreements—with fluency in Code §§ 409A, 457(f), 280G, and 162(m).  Cher negotiates with the IRS, DOL, and PBGC and turns audits into closure. In deals, she solves ERISA issues—pensions, cash balance, CBAs, retiree health—without slowing the transaction. She guides ACA compliance, wellness, HIPAA, and HITECH. Cher has particular expertise in the defined benefit plan sector, including specialized investment review and “side letter” drafting for governmental and institutional pension plan clients. For companies, nonprofits, health systems, and public entities, her work delivers durable, compliant plans that attract leaders and sustain performance.

Notable Work & Achievements

Cher’s portfolio sits where strategy meets regulation. She advises leading nonprofit health systems and major companies on executive pay, retirement, and health and welfare programs. Her work aligns board priorities with the expectations of the IRS, DOL, and PBGC, keeping plans both competitive and compliant.

In fast moving transactions, Cher leads the benefits workstream. She integrates tax qualified plans, harmonizes union and nonunion benefits, resolves Section 280G and change in control issues, and negotiates executive employment and separation agreements. Closings stay on schedule and leadership stays focused on the deal.

Operationally, Cher redesigns benefits for durability. She has moved clients from legacy defined benefit plans to modern safe harbor 401(k) structures, transitioned recordkeepers, set up ERISA 3(21) fiduciary frameworks, and streamlined vendor contracts including investment advisory and consulting, self-insured ASOs and PBM contracts. The result is lower friction, stronger cost control, and a better participant experience.

When regulators call, Cher moves matters to closure. She handles audits, corrections, and voluntary compliance filings. She also builds HIPAA and HITECH policies and training that help organizations manage privacy and security risk. Her clients include corporations, tax exempt organizations, large health systems, and public bodies. Each engagement requires clear judgment, steady execution, and benefits that perform under pressure.

Recognitions

  • The Best Lawyers in America, Employee Benefits (ERISA) Law (Recognized since 2008)
  • Virginia's "Legal Elite," Virginia Business magazine, Business (2012-2013, 2018-2022)
  • Virginia "Top 50 Women," Virginia Super Lawyers magazine, Employee Benefits
  • Virginia Super Lawyers, Employee Benefits (2017-2023)

What does Structured for Solutions mean to you and how do you apply that to your work?

Being "Structured for Solutions" means matching benefit design to business outcomes—and staying two steps ahead of regulators. I start with the client’s goals, then build plans and agreements that are durable, compliant, and practical to administer. I anticipate IRS/DOL scrutiny, simplify vendor relationships, and translate technical rules into clear decisions so leadership can move with confidence.