Position SummaryThe Benefits Division’s focus is to provide a quality health benefits package that serves the needs of both the organization and its employees. The Deputy Director of Health and Welfare directs the design and administration of the City Administered Benefits Plan for active employees and retirees, with a strong focus on health equity and wellbeing. Many initiatives are primarily intended to promote health literacy, and healthy lifestyles of employees, and families while effectively managing costs.The Deputy Chief Human Resources Officer (DCHRO) of Health and Welfare reports to the Chief Human Resources Officer for the City.  The position provides effective management of employees benefits though vendor relationships  and direction of  activities including health provider contract solicitation and evaluation, oversight of the  union-administered plans for active and retiree members, administration of citywide life insurance, dependent care, and transportation benefits, payment validation for self-insured union plans, provision of retiree data for actuarial analysis for inclusion in the City’s Annual Financial Report, maintenance of data on incurred-but-not-paid claims, annual provision of the 1095 form for employee tax compliance, administration of the City’s service-connected disability program under Regulation 32, and provision of ongoing training for HR representatives in client departments. City Representation, Trustee for all City Health and Welfare Union Funds.Essential FunctionsThe DCHRO of Health and Welfare has responsibility for key areas that include strategic direction, financial oversight, program management, and compliance.Designs, implements, and refines the company's health and welfare plans for active and retiree populations. This includes medical, prescription, dental, vision, life insurance, wellness, EAP, FSA other ancillary benefits include: Back up Care/ Concierge Services, Pregnancy / Postpartum / Menopause, Voluntary Benefits include: Term Life, Hospital, Accident, Critical Illness, Pet Insurance.Stewards financial resources and monitors budget and performance of all benefits plans; negotiates with carriers and vendors to manage costs and ensure a competitive and fiscally sound benefits portfolio.Engages and maintains relationships with all third-party vendors, including insurance companies, benefit administrators, and wellness providers.Ensures all benefits programs comply with complex federal and state laws, such as the Affordable Care Act (ACA), COBRA, ERISA, HIPAA, FMLA and Medicare.Leads Health literacy communications to educate the HR community and City employees about benefits and champions change to improve health outcomes. Directs a team of benefits professional and administrative staff, providing technical direction and guidance as well as growth and development in all aspects of health and welfare program administration.Reports on the status and performance of benefits programs to the Mayor, City Council, and other key City officials.And other duties as assigned.Required Competencies, Knowledge, Skills, and AbilitiesKnowledge of:Principles and practices of employee benefits administration, including medical, prescription, dental, vision, life insurance, FSA / Health/ Dependent Care and Commuter Benefits, wellness programs and voluntary benefits.Federal, state, and local laws governing employee benefits, including ACA, HIPAA, COBRA, FMLA, ERISA, Medicare and related compliance requirements.Health plan design, funding strategies, and cost containment methods for large, complex organizations.Collective bargaining agreements and the interaction between union-administered and City-administered benefit programs.Actuarial principles, financial reporting requirements, and data analytics used to evaluate plan performance, incurred-but-not-paid claims, and retiree health liabilities.Demonstrated thorough understanding and articulation of group health plans, insurance principles, and benefits administration is essential.Skill in:Strategic program design and evaluation to balance employee wellness with fiscal sustainability.Negotiating and managing contracts with benefit providers, consultants, and third-party administrators to ensure value and accountability.Analyzing and interpreting complex data, including claims experience, utilization trends, and actuarial valuations, to inform policy decisions.Leading and developing multidisciplinary teams responsible for benefit operations, compliance, and customer service.Communicating complex benefit concepts clearly and persuasively to executive leadership, unions, employees, and external stakeholders.A strong command of the complex legal landscape governing employee benefits is mandatory.Ability to:Develop and implement comprehensive benefits strategies that align with organizational goals and promote employee well-being.Ensure compliance with all applicable benefit laws, regulations, and reporting obligations, including preparation of annual filings and tax documentation (e.g., 1095 forms).Collaborate effectively with union representatives, actuaries, finance staff, and departmental HR offices to resolve complex benefit issues.Evaluate program effectiveness through metrics and performance indicators, recommending data-driven improvements to enhance outcomes and control costs.Exercise sound judgment and confidentiality in handling sensitive employee, financial, and health information.The ability to lead a team, manage vendors, and communicate with diverse stakeholder audiences and employees is critical.Advocacy for improving disparate health outcomes among varied employee populations and fostering access to quality health and wellness coverage and resources.