Robert M. Cipolla

Rob finds practical business solutions that meet each client’s needs arising within the technical regulatory framework of employee benefits law under ERISA and the Internal Revenue Code. He has significant experience advising clients regarding the design, administration, operations, reporting, and disclosure of defined benefit plans, 401(k) retirement plans, 403(b) and 457 plans, employment agreements, non-qualified deferred compensation plans, multi-employer plans, and health plans.

Rob helps employers attain favorable rulings from the IRS, DOL, and other governmental agencies, and he assists clients in obtaining the desired outcomes in audits by such agencies.

Rob has significant experience advising both public and private clients on the employee benefit and executive compensation aspects of mergers and acquisitions, which he uses to help clients assimilate plans and workforces following transactions.

Since 2021, Rob has been recognized by Chambers USA as a leading lawyer for Employee Benefits & Executive Compensation, most recently in 2024 (Band 4, District of Columbia). 

A member of the Central Virginia Employee Benefits Counsel and the American Bar Association, Rob regularly speaks at employee benefit programs and conferences. He has taught classes at the Southeastern Trust School.

Rob joined Calfee as a Partner in 2024 from McGuireWoods.

Rob earned his J.D. from the Cleveland State University College of Law at night while working for a large national accounting firm during the day.

Honors & Recognitions

• Chambers USA, Employee Benefits and Executive Compensation, Band 4, District of Columbia (2024)
• Legal 500 United States, Employee Benefits, Executive Compensation and Retirement Plans: Transactional (2022, 2023) and Employee Benefits, Executive Compensation and Retirement Plans: Design (2023)
• The Best Lawyers in America^®, Employee Benefits (ERISA) Law (2009-2025)
• The Best Lawyers, “Lawyer of the Year,” Employee Benefits (ERISA) Law, Richmond, Virginia (2025 and 2021)

Education

J.D., Cleveland State University College of Law, 1994

B.S., Virginia Polytechnic Institute and State University, 1988

Experience

The following experience was gained while serving as a Partner at a previous law firm:

• Thirty years of experience with defined benefit pension plans, defined contribution plans, and non-qualified plans in all compliance matters, including non-discrimination testing, VCP and IRS submissions, fiduciary advice, prohibited transaction exemptions and private letter rulings, and day-to-day compliance issues.
• Regularly advised plan fiduciary committees with respect to fiduciary duties and responsibilities.
• Advised trustees of multiemployer pension plan.
• Obtained a private letter ruling from the IRS that saved a plan sponsor $20 million in additional pension costs.
• Represented a public company in the spin-off of a new public company; assisted the companies in the establishment of all employee benefit plans for the new public company, including defined benefit plans, defined contribution plans, executive compensation plans, and welfare benefit plans.
• Represented and assisted plan fiduciaries in transferring $700 million in pension assets and liabilities to insurer (“annuity lift out”).
• Advised on the design and restructuring of several defined benefit pension plans and defined contribution plans for a Fortune 500 company.
• Represented several university general counsels and boards of trustees in the design and negotiation of employment agreements and deferred compensation plans for executive officers and athletic coaches.
• Represented a multinational corporation in a merger and identified $2 million in savings from potential costs associated with non-compliant, non-qualified deferred compensation plans.
• Advised public and private companies with respect to equity and phantom equity compensation plans, grant agreements, and necessary disclosures.
• Advised public companies with the compensation discussion and analysis of the yearly proxy disclosures.
• Chairman of Retirement Plan Investment Committee of previous law firm from 2016-2023.

Professional & Community

Central Virginia Employee Benefits Counsel, Member

Southeastern Trust School, Former Adjunct Faculty Member

Presentations

• Speaker, "Excess Benefit Transactions/Senior Leadership Compensation Structures," 19th Annual Nonprofit Seminar, Richmond and Charlottesville, September – October 2022.
• Speaker, "Employee Benefits," Annual Nonprofit Seminar, November 2010 – 2022.