Health care organizations, large financial services companies, and not-for-profit and tax-exempt institutions, among others, look to attorney Cassandra Labbees to address compliance-related issues for non-qualified and tax-qualified plans under the Internal Revenue Code and ERISA, health and welfare plans, and the Affordable Care Act (ACA).

With insights gained from working as an investigator for eight years at the U.S. Department of Labor’s Employee Benefits Security Administration (EBSA), Cassandra helps clients spot issues they may have overlooked and provides creative solutions and practical advice to ensure that clients’ needs are met.

Clients appreciate Cassandra’s knack for issue-spotting, strong communication skills, ability to talk to all levels of compliance teams, and efficiency. Cassandra helps clients reduce or defeat penalties and firm up their processes when it comes to their fiduciary obligations.

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Companies turn to Cassandra to design, implement, maintain, and terminate their employee benefit plans. She assists them with compliance-related issues for defined contribution, defined benefit, self-insured and fully insured health and welfare plans, including medical, life, disability, employee assistance programs, wellness plans, cafeteria plans, flexible spending accounts, severance plans, and other types of compensation and benefits arrangements. She also counsels clients on compliance with all aspects of the ACA, including ACA reporting and assistance, employer mandate penalty assessments, applicable large employer determinations, and controlled group analysis.

In addition, Cassandra reviews service provider agreements. She advises clients on compliance issues related to multiple employer welfare arrangements (MEWAs), association health plans, and professional employer organizations (PEOs). She assists clients with audits of benefit plans by the U.S. Department of Labor and corrections of plan errors under the Internal Revenue Code.

For companies contemplating a merger or acquisition, Cassandra advises on the impact of the transaction on employee benefit plans and assists with plan termination and integration.

While at the EBSA, Cassandra conducted compliance audits of employer-sponsored group health plans and qualified retirement plans to ensure compliance with ERISA. She worked with Assistant U.S. Attorneys and local district attorneys to handle criminal investigations of fraud and theft involving employee benefit plans.

Cassandra speaks frequently on ERISA fiduciary basics and employee benefit issues.

While attending law school, Cassandra was a legal intern at the Legal Aid Society – Juvenile Rights Division, at the St. John’s Child Advocacy Clinic, and for the Honorable Ruben Martino of the Harlem Community Court in New York City.

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Focus Areas


  • Represented a global financial institution that acquired an entity with many compliance issues that posed a risk of affecting the client’s own retirement plan. Cassandra worked with the client, consultant, and record-keeper to correct all the errors, file the appropriate filings with the regulator, and clean up all errors to put it back in compliance with ERISA and the Internal Revenue Code.
  • Represented a health and wellness company that was assessed a large penalty by the U.S. Department of Labor for filing failures. Cassandra assisted the client with correcting the errors, finding out the lapse in its processes, and submitting the applications to the IRS. The client’s penalty was reduced significantly and its processes were firmed up to prevent such an error in the future.
  • Represented a medical group whose group health plan was audited by the Department of Labor. Cassandra helped the client make corrections as required by the regulators.


  • The Legal 500 United States recommended attorney in Employee Benefits, Executive Compensation, and Retirement Plans: Design (2019, 2023)



  • St. John’s University School of Law (J.D., 2007)
  • State University of New York at Albany (B.A., 2004)

Bar Admissions

Professional & Community Involvement

  • New York City Bar Association, Employee Benefits and Executive Compensation Committee
  • Metropolitan Black Bar Association





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