Mr. Gregory’s practice is focused primarily in the areas of ERISA, employee benefits, and executive compensation. Mr. Gregory advises clients on all aspects of employee benefits including qualified retirement plans, welfare plans, and nonqualified compensation programs.
Mr. Gregory assists clients with plan design, drafting, and implementation of 401(k), profit sharing, 403(b), 457, and defined benefit plans. Mr. Gregory also provides advice on the design, implementation, and administration of insured and self-insured medical plans, dental plans, life insurance, disability, and cafeteria plans, including pre-tax premium plans, and flexible spending account plans.
Additionally, Mr. Gregory assists clients regarding regulatory compliance with HIPAA, the Affordable Care Act (healthcare reform), COBRA, FMLA, GINA and ADA.
He also assists clients with privacy and security concerns, including the privacy implications of HIPAA and state laws.
Mr. Gregory has advised numerous state and local retirement plans.
He regularly provides strategic advice and analysis on approaches for employers obligated to contribute to multiemployer pension funds to mitigate withdrawal liability risk.
Also, Mr. Gregory assists clients with federal, state and local tax implications of compensation programs and corporate transactions.
In addition to his legal practice, Mr. Gregory is currently a member of the Tax Council of the State Bar of Michigan Taxation Section. He was previously Chair of the Employee Benefits Committee of the Taxation Section (2017-2019). He is also a member of the Oakland County Bar Association’s Employee Benefits Committee, where he previously served as Chair (2016-2017) and Vice Chair (2015-2016). Mr. Gregory is a Board Member of Lakeshore Legal Aid, which is the largest non-profit legal aid program in Michigan, providing civil services to low-income families and seniors in 17 counties.
He is a frequent speaker and author on employee benefits and tax issues.
Education & Credentials
Education
Michigan State University, James Madison College
B.A., Political Theory and Constitutional Democracy, 2008- With high honor and honors diploma
- Phi Beta Kappa
Wayne State University
J.D., 2012- Margaret S. Raben Scholarship for Academic Excellence
Georgetown University Law Center
LL.M., Taxation, Certificate in Employee Benefits Law, 2013Bar Admission
Acknowledgements
- 40 under 40 Class of 2024, Oakland County Executive, Oakland Together
- Chambers USA: America's Leading Lawyers for Business
- Employee Benefits & Executive Compensation, 2016-2024
- Best Lawyers in America®
- Employee Benefits (ERISA) Law, 2020-2025
- "Lawyer of the Year," Employee Benefits (ERISA) Law, 2025
- Michigan Lawyers Weekly
- "Up & Coming" Lawyer, 2017
- DBusiness Magazine
- "Top Lawyer," Employee Benefits Law, 2016-2021
- Michigan Super Lawyers®
- "Rising Star," Employee Benefit Law, 2016-2024
Prominent Assignments
- Provided advice to plan administrative and investment committees on fiduciary compliance.
- Corrected complex retirement plan administration errors using the IRS’ Employee Plans Compliance Resolution System.
- Successfully challenged millions of dollars in proposed assessments made under the “pay-or-play” provisions of the Affordable Care Act.
- Provided employee benefit due diligence and benefit transition advice for both buyers and sellers in the mergers and acquisitions context.
- Advised clients regarding Code Section 409A compliance for deferred compensation plans and in-kind benefit programs.
- Counseled employers with respect to multimillion dollar withdrawal liability allegations.
- Assisted employers in avoiding and responding to data breaches, including breaches of Protected Health Information under HIPAA.
- Provided advice to numerous clients regarding record retention, privacy, and security policies and in addressing privacy breaches.
- Advised clients on the design and implementation of numerous fringe benefit programs, including the federal, state, and local tax implications.
- Resolved issues regarding delinquent and incomplete Form 5500 filings with the Department of Labor.
- Assisted employers with complex payroll withholding and employee classification issues, including tax compliance for foreign workers.
Professional Involvement
- State Bar of Michigan – Taxation Section, Taxation Council Member (2019 – Present); Employee Benefits Committee (Chair, 2017 - 2019)
- Oakland County Bar Association - Employee Benefits Committee (Chair, 2016-2017; Vice Chair, 2015-2016)
- American Bar Association – Taxation Section; Joint Committee on Employee Benefits
Community Involvement
- Board Member, Lakeshore Legal Aid, 2016 - Present
- Past Board Member, Free Legal Aid Clinic - Detroit
Court Admissions
- United States Tax Court
Publications/Presentations
Publications
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Author, "The Top Affordable Care Act Reporting Mistakes We Continue to See in 2024" Dickinson Wright HR Blog, May 2024
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Author, "Potential audits of the employee retention tax credit," Michigan Bar Journal, December 2023
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Author, "An Informed Guide To Mastering Retirement Plan Forfeitures," Law 360, December 2023
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Practicing Law Institute Chronicle, “The Evolving Mental Health Parity Requirements for Plan Sponsors: Key Considerations and Action Steps”
- Author, "IRS Issues Alerts and Begins Audit Activity Related to the Employee Retention Tax Credit," Dickinson Wright Legal Edge Blog (June 2023)
- Author, "Action Items Plan Sponsors Should Consider in the Wake of the U.S. Supreme Court Dobbs Decision on Abortion," LexisNexis (August 2022)
- Author, "Avoiding Costly "Employer Payment Plan” Status for Travel Benefits," LexisNexis (July 2022)
- Author, “Missing Participants Policy and Procedures,” Lexis Practice Advisor (July 2020)
- Author, “Debunking SPD Myths Series,” Lorman Human Resources Series (February 2020)
- Author, “Considerations for Plan Sponsors Who Discover Unauthorized Workers in Their Retirement Plans,” Employee Benefit Plan Review, Volume 73, Issue 9 (November/December 2019)
- Author, “6th Circuit Court Rules Retiree Health Benefits May be Terminated Based on Contract Principles,” Lorman Human Resources Series (May 2019)
- Author, “Is it Time to Consider if a Retiree Lump Sum Window is Appropriate?,” Lorman Human Resources Series (April 2019)
- Author, “Employers, There May Be No Such Thing As A Free Lunch,” Law360 Expert Analysis (February 2019)
- Author, “Avoiding Payroll Tax Traps For Foreign Employees,” Law360 Expert Analysis (February 2019)
- Author, “Intra-Agency Inconsistency among ERISA’s Three-Headed Guardians: Despite Additional Clarifications and New Programs, Significant Gaps Exist with Respect to Missing Retirement Plan Participants” The Michigan Tax Lawyer, Volume XLIV, Issue 2 (Spring 2018)
- Author, “EBSA Formally Delays Implementation of Final Rule on Disability Claims Procedures” Employee Benefit Advisor (December 2017)
- Author, “The Narrow but Significant Impact of the Department of Labor’s New Fiduciary Rule on Employers that Sponsor Retirement Plans” Oakland County Bar Association Laches Magazine (September 2017)
- Author, “What an Employee Benefits Attorney Would Like Estate Planners to Know about Employer-Sponsored Retirement Plans,” Michigan Probate & Estate Planning Journal, Volume 36, Number 2 (Spring 2017)
- Author, “Surviving an IRS or DOL Retirement Plan Audit: Failing to Prepare is Preparing to Fail,” Oakland County Bar Association Laches Magazine (March 2017)
- Author, “Here Comes the Department of Labor: Retirement Plan Audits Begin for Code Section 401(a)(9) Compliance,” Michigan Bar Journal, Volume 95, Number 9 (September 2016)
- Author, “The IRS Overhaul of the Determination Letter Process: What Plan Sponsors Need to Know,” Employee Benefit Plan Review, Volume 71, Issue 1 (July 2016)
- Author, “From Hollywood to HIPAA: How Healthcare Data Breaches Can Affect Your Clients and What You Can Do About Them,” Oakland County Bar Association Laches Magazine (October 2015)
- Author, “The IRS Announces an Overhaul to the Determination Letter Process: Why it Matters and What Plan Sponsors Need to Know,” The Michigan Tax Lawyer, Volume XLI, Issue 2 (Summer/Fall 2015)
- Author, “Employer-Paid Individual Health Insurance Policies Create the Potential for Significant Penalties, but Limited Relief is Available,” Employee Benefit Plan Review, Volume 70, Issue 10 (August 2015)
- Author, “The IRS Issues New Guidance on the Economic Substance Doctrine,” The Michigan Tax Lawyer, Volume XLI, Issue 1 (Winter 2015)
- Author, “Welcome the Department of Labor to the 21st Century: Using Free Search Tools to Find Missing Defined Contribution Plan Participants,” Oakland County Bar Association Laches Magazine (October 2014)
- Author, “Significant Penalties on the Horizon: Nondiscrimination Rules for Fully Insured Health Plans,” The Michigan Tax Lawyer, Volume XL, Issue 3 (Fall 2014)
- Author, “Missing State Rules in the Wake of United States v. Windsor: A Lack of Guidance from the Michigan Department of Treasury for Same Sex Couples Legally Married in Other Jurisdictions,” The Michigan Tax Lawyer, Volume XL, Issue 1 (Winter 2014)
Presentations
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Co-Presenter, “Getting Ahead of the New Retirement Plan Fiduciary Rules - Legal and Investment Insights,” 2024 MISHRM Conference, Michigan Society of Human Resource Management, October 2024
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Speaker, “New Disclosures, Fees, and Litigation Challenges for ERISA Health Plans,” 36th Annual Tax Conference, State Bar of Michigan Taxation Section & Institute of Continuing Legal Education, May 2024
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Co-Presenter, “Building a Better Fiduciary Process in 2024 for Retirement Plan Sponsors,” Employee Benefits Webinar, Dickinson Wright, April 2024
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Speaker, “The Top 10 Compliance Mistakes with Health & Welfare Plans,” 2024 LoVasco Benefits Briefing, LoVasco Consulting Group, April 2024
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Co-Presenter, “Legal Update Panel: When the Government Comes Calling,” DSHRM 2024 Conference, Detroit Society for Human Resource Management, 2024
- Detroit Society for Human Resource Management 2023 Conference, “Navigate a Mock Acquisition” Co-Panelist (September 2023)
- Lorman Webinar, “ERISA Audits: What We All Knew but Forgot” Presenter (August 2023)
- Speaker, "Dobbs and Employee Benefits Issues," Practical Guidance Podcast: Labor and Employment Series (August 2022)
- Co-Presenter, “An Employer’s Guide to the Benefits Provisions of the CARES Act and Other COVID-19 Benefits Concerns” Detroit Society for Human Resource Management (April 2020)
- Co-Presenter, “Families First Coronavirus Act Playbook” Middle Tennessee Society for Human Resource Management (April 2020)
- Presenter, “Critical Challenges Facing Pension Withdrawal Liability” Lorman Webinar (March 2020)
- Co-Presenter, “Pandemic Workplace Response: Now What?” Detroit Society for Human Resource Management (March 2020)
- Presenter, “Unauthorized Workers in Retirement Plans, Key Considerations for Plan Sponsors and ERISA Counsel: ERISA and DOL Guidance, Tax Reporting and Withholding Issues for U.S. and Non-U.S. Persons, Incorrect or Missing Information,” Strafford Webinar (December 2019)
- Co-Presenter, “Retirement Plan Audits: Recognizing Plan Errors, Remedying Noncompliance, New IRS and DOL Audit Initiatives: Effective Procedures and Corrective Actions for 401(k), 403(b), and Other Retirement Plans,” Strafford Webinar (October 2019)
- Presenter, “Employee Benefits Considerations for Today’s Mobile and Global Workforce,” Oakland County Bar Association Employee Benefits Committee (June 2019)
- Presenter, “Employee Benefits: Avoiding the Silent, Unseen Traps for Estate Planners” The Institute of Continuing Legal Education, 28th Annual Drafting Estate Planning Documents Seminar (February 2019)
- Co-Presenter, “Telemedicine Hot Topics for Providers and Employers - What's Hot, What's Not, and What's Next?” Dickinson Wright PLLC Webinar (December 2018)
- Co-Presenter, “"The Top 10 Insider Tips for Operating a Gold Standard 401(k) and 403(b) Retirement Plan" Dickinson Wright PLLC Sunrise Seminar (October 2018)
- Presenter, “Don’t Forget Pension and Employee Benefits Liability During M&A” Michigan Association of CPAs Management Information & Business Show and West Michigan Management Information & Business Show (May and June 2018)
- Presenter, “Avoid the Wave of Litigation: Managing Risk and Liability for Employer-Sponsored Retirement Plans” Troy Chamber of Commerce Choose Troy Series (January 2018)
- Co-Presenter on Nonqualified Plans and Fringe Benefits, “Tax Law Series: Employee Benefits-Related Tax Issues” Institute of Continuing Legal Education (November 2017)
- Presenter, “2017 Fiduciary Litigation Update” Oakland County Bar Association Employee Benefits Committee (October 2017)
- Co-Presenter on Cybersecurity Issues, “You Can't Make This Stuff Up! Things We Wished Our Clients Asked Us Ahead of Time!” International Society of Employee Benefits Specialists Educational Seminar (June 2017)
- Presenter, “Employee Benefits Year In Review,” Employment Matters, A Year in Review, Oakland County Bar Association Employment Law Committee (June 2017)
- Presenter, “Wearable Health Technology and HIPAA: Know Whether Your Company is Violating the Regulations in 2016,” The Knowledge Group Seminar (November 2016)
- Co-Presenter, “Employee Benefits Law,” Oakland County Bar Association OCBA U Series (October 2016)
- Presenter, “Issue Spotting in a Post-Obergefell World,” Oakland County Bar Association Continuing Legal Education Seminar (September 2016)
- Presenter, “2016 + ACA – New Rules on an Existing System,” Michigan Association of CPAs Insurance Conference (September 2016)
- Presenter, “Affordable Care Act: 2016 Update,” Oakland County Bar Association Employee Benefits Committee (September 2016)
- Presenter, “Help Me, Help You: ACA Filings,” Michigan Association of CPAs and IRS: Successfully Working Together Conference (June 2016)
- Presenter, “ERISA Fiduciary Duty for Retirement Plan Investment Decisions: Managing Risk, Avoiding Liability, and Improving Function” Dickinson Wright PLLC Sunrise Seminar (April 2016)
- Presenter, “ACA Updates, Reporting and Forms…Oh My!” Dickinson Wright PLLC Sunrise Seminar (October 2015)
- Presenter, “Determination Letter Program Update: What Plan Sponsors Need to Know,” State Bar of Michigan Taxation Section, Employee Benefits Subsection (September 2015)
- Presenter, “The Best Data Practices for ERISA Fiduciaries,” Oakland County Bar Association Employee Benefits Committee (March 2015)