Closing Date: 15th July, 2026

Description:

Job Description:
The Office of Labor Relations (OLR) represents the Mayor in the conduct of all labor relations between the City of New York and labor unions representing employees of the City. The Commissioner serves on behalf of the Mayor as the City's liaison with both labor and management in the private sector. The office is authorized by Executive Order 38 (February 7, 1967), amended by Executive Order 13 (July 24, 1990).

Additionally, OLR administers the Health Benefits Program, Management Benefits Fund, Employee Assistance Program, Work Well NYC, Medicare Part B Reimbursement and Pre-Tax Benefits & Citywide Programs including the Deferred Compensation Plan and NYCE IRA. In addition to negotiating collective bargaining agreements, OLR serves as a resource to agencies with regard to workforce labor issues and works with the Municipal Labor Committee (MLC) to pursue innovations in a variety of areas, particularly regarding City health insurance programs. The staff at OLR assist their fellow agencies in handling personnel and payroll issues, conducting labor-management meetings, representing the City at representation hearings, and handling all employee grievances and arbitration matters while also negotiating collective bargaining agreements with the City's 149 bargaining units.

Office of the General Counsel (OGC): Under the supervision of the General Counsel, OGC serves as the agency's legal counsel, providing legal support and advice agency-wide on the wide range of issues that arise at the agency given the breadth of its portfolio. In addition to advising on collective bargaining and labor relations, the legal team attorneys represent the city before the Office of Collective Bargaining (OCB) in administrative proceedings, including arbitrations, and serve as neutrals during Step III grievance proceedings. The legal team is also responsible for contracts administration across the various procurements held by OLR's administered programs. Further, OGC is responsible for ensuring compliance with the various regulatory requirements that set the legal framework for the employee benefits programs that serve the city's approximately 300,000 employees and city retirees and their dependents. Lastly, the legal team liaises with the Law Department on litigation, discovery, and is responsible for FOIL, privacy, and the other day-to-day legal matters that arise for an agency's in-house counsel team.

Job Summary:
OGC seeks a seasoned attorney to serve as Special Counsel to develop and evolve the agency's compliance framework and systems for the management of the agency's healthcare, and employee benefits. Reporting into the General Counsel and serving as a member of OGC's leadership on a team of approximately 15 legal and procurement professionals, the Special Counsel will provide legal counsel on employee health benefits, including group health plans, supplemental benefits, wellness programs, and Federal/New York State regulatory compliance. Further, the Special Counsel will be responsible for designing a short-term and long-term operational plan for the development of the agency's compliance and privacy infrastructure, development of key performance indicators, and policy development with respect to the data generated by the benefits and plans the agency manages.

The successful candidate must have experience with and interest in the applicable regulatory legal framework, policy, and in designing and operationalizing compliance systems. They must be self-starter, curious, driven, and able to work holistically with the various stakeholders who need to be engaged as OLR evolves to better meet the needs of the city's health and benefits plans. The successful candidate must be a strategic thinker, possess strong communication skills, organized, detail-oriented, and solutions oriented. While expertise in ACA, HIPAA, COBRA, and other relevant federal and New York State laws and regulations is a plus, the successful candidate must show the ability and desire to develop a strong foundation in the relevant regulatory frameworks and an actionable plan for success. They must be eager to learn, a problem solver who can work both collaboratively and independently without close supervision, and understand the many facets and interests involved in making decisions and investments that impact on the city's workforce as a whole. Patience, flexibility, sound judgment, creativity, and a good sense of humor to help ensure a collegial environment are also necessary for successful integration to OGC's small (but mighty) team.

Key responsibilities include but are not limited to:

Provide legal guidance on the design, implementation, and administration of health and employee benefit plans, specifically the city's self-funded group health plans;
Ensure organizational compliance with ACA, HIPAA, COBRA, and other federal/New York State laws governing employee health benefits programs;
Advise on legal risks and mitigation strategies related to employee benefits, health benefits and wellness programs;
Design and, with OLR leadership buy-in, operationalize a scalable compliance framework that is actionable within the relevant budgetary constraints;
Work with OGC and agency leadership to identify tools and investments that could meet needs of compliance and OLR efficiently;
Liaise with outside counsel and law department on matters associated with the city's benefits plans;
Work with the Agency Privacy Officer (APO) to develop relevant policies and conduct use case analysis for any data or tech investments in the agency's infrastructure;
Draft, review, and negotiate contracts with employee benefit plan vendors, third-party administrators, consultants, and insurers;
Support audits and governmental inquiries from federal/New York State agencies;
Monitor and interpret changes in federal/New York State laws/regulations governing employee benefits programs and communicate their impact to executive decision-making team;
Collaborate with the employee benefits administration team to develop and regularly update plan communication materials, policies and procedures;
Assist in dispute resolution and litigation involving employee benefit plans; and
Additional duties as assigned.

Executive Agency Counsel - 95005

Minimum Qualifications:
Admission to the New York State Bar; and four years of recent full-time responsible, relevant, satisfactory legal experience subsequent to admission to any bar, eighteen months of which must have been in the supervision of other attorneys, in an administrative, managerial or executive capacity, or performing highly complex and significant legal work.

Incumbents must remain Members of the New York State Bar in good standing for the duration of this employment.

Public Service Loan Forgiveness
As a prospective employee of the City of New York, you may be eligible for federal loan forgiveness programs and state repayment assistance programs. For more information, please visit the U.S. Department of Education's website at https://studentaid.gov/pslf/.

Residency Requirement:
New York City Residency is not required for this position

Additional Information:
The City of New York is an inclusive equal opportunity employer committed to recruiting and retaining a diverse workforce and providing a work environment that is free from discrimination and harassment based upon any legally protected status or protected characteristic, including but not limited to an individual's sex, race, color, ethnicity, national origin, age, religion, disability, sexual orientation, veteran status, gender identity, or pregnancy.