Yelena F. Gray

Yelena Gray advises employers of all types and sizes on issues related to employee benefit plan design, implementation, administration and regulatory compliance. Yelena also assists clients in negotiating employment agreements and structuring executive compensation.

What do you focus on?

I assist employers with the design and operation of employee benefit plans in the exceedingly complex regulatory environment. Leveraging 17 years of experience advising private, public, tax-exempt and employee-owned companies, I provide the depth and prospective in the employee benefits arena that my clients seek.

Welfare Benefit Plans Compliance

I assist employers with the analysis of their workforce and employee benefit offerings, both from the perspective of economic and staffing needs and to ensure compliance with legal mandates. My recent experience runs the gamut of compliance, design, implementation, drafting and day-to-day administration of group health and cafeteria plans, flexible spending and health care reimbursement arrangements, as well other welfare benefit programs. I guide employers in their efforts to determine the impact of health care reform on their group health care plans, update their plan documentation and ensure compliance with the requirements of ACA, HIPAA, COBRA, mental parity and state laws affecting the design and administration of health and welfare plans.

Qualified Retirement Plan

I advise employers in matters involving qualified retirement plans, including plan design and drafting, monitoring compliance with new legislation and regulatory guidance, communicating with regulatory agencies and counsel on issues of fiduciary responsibilities. I have been involved in obtaining determination and private letter rulings from the Internal Revenue Service (IRS), assisting clients in negotiating pension plan audits and advising clients regarding the IRS programs for correcting plan qualification defects and the Department of Labor voluntary fiduciary correction programs. My recent experience includes assisting clients in matters involving leveraged ESOP buyouts and administration. My work also includes counseling employers on unique issues of compliance and administration affecting cash balance plans.

Executive Compensation

I advise clients regarding executive compensation plans, including matters of compliance with the requirements of Section 409A of the Internal Revenue Code and issues involving change in control, employment and severance agreements, as well as equity and incentive compensation arrangements.

What do you see on the horizon?

The regulatory landscape in the employee plans arena is changing daily and will ultimately shape employers’ benefits offerings. Employer shared responsibility rules, market reforms and “the Cadillac tax” are already prompting employers to take a fresh look at their plans. Audit activity is picking up in several areas, including fiduciary processes and welfare benefit plans. In this environment, it’s difficult to underestimate the effects of careful allocation of responsibilities with respect to employee benefit plans, advance planning and appropriate documentation.


  • Presenter, “Information Reporting Requirements Under Code Sections 6055 & 6056,” ABA Section of Taxation Fall Meeting, September 18-20, 2014
  • Presenter, "Square Pegs and Round Holes: Benefit Classification under Final MHPAEA Regulations," ABA Section of Taxation Midyear Meeting, January 23-25, 2014
  • Presenter, "ACA Health Plan Compliance: New Employer Mandate, Plan Documentation and Requirements, Fiduciary Responsibilities," Strafford Webinar, December 17, 2013
  • Presenter, "Impact of the Omnibus Final HIPAA Rule on Employers," ABA Section of Taxation Fall Meeting, September 19-21, 2013


  • “New law puts brakes on health-care reimbursements for employees,” Chicago Daily Law Bulletin, September 22, 2015

New law requires health plans to demonstrate compliance with parity requirements between mental health and medical benefits

Employee Benefit Plan Review | June 10, 2021

Chicago partner Yelena Gray, Washington DC partner Damian Myers, and Rochester associate Lena Gionnette, all of the Corporate group, contributed this article analyzing the new federal laws requiring employer-sponsored group health plans to prove that their plans satisfy all aspects of the parity regulations between mental health and medical benefits.

Stakeholders await key guidance on full COBRA subsidies

Inside Health Policy | March 26, 2021

Rochester Corporate partner Brian Kopp, of the Employee Benefits & Executive Compensation team, is quoted in this article on COBRA subsidies included in the newly enacted American Rescue Plan, noting potential challenges for employers. The article also links to a client alert Brian wrote with Chicago Corporate partner Yelena Gray and Washington, DC Corporate partner Damian Myers, both of the Employee Benefits & Executive Compensation team.

Stimulus legislation gives temporary relief under flexible spending arrangements

Journal of Compensation and Benefits | March 12, 2021

Washington, DC partner Damian Myers, Chicago partner Yelena Gray, and Rochester associate Lena Gionnette, all of the Corporate group and Employee Benefits & Executive Compensation team, contributed this article summarizing the temporary relief for flexible spending accounts in the December 2020 stimulus law, highlighting important takeaways for plan sponsors.

3 Tips on Complying with the New Mental Health Parity Law

Law360 | February 10, 2021

Chicago partner Yelena Gray and Washington, D.C. partner Damian Myers, both of the Corporate group and Employee Benefits & Executive Compensation team, are quoted throughout this article on steps employers can take to ensure they are in compliance with the mental health parity law that took effect on Wednesday.


Yelena F. Gray



Phone: 312-977-4158

Fax: 844-571-5875

Indiana University School of Law, J.D., summa cum laude

Kherson Pedagogical Institute, Russian Language and Literature Diploma, high honors




  • Taxation Section, American Bar Association
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