Senior Director of Workforce Operations and Program Management

Job Overview:

Department: Employment ServicesLocation: Fully onsiteEmployment Type: Full Time, RegularSalary Range: Commensurate with experience $110,000–125,000

About Us

Henry Street Settlement is a mission-driven, community-based organization dedicated to advancing economic equity, education, and opening doors of opportunity in underserved communities. We deliver workforce development programs, youth services, job training, and economic mobility initiatives that empower individuals and strengthen families.

Position Summary

The Senior Director of Workforce Operations and Program Management is a key member of the workforce development senior leadership team responsible for overseeing the strategic direction, operational efficiency, and programmatic excellence of workforce development initiatives. This role will ensure programs are responsive to community needs, aligned with labor market demands, and delivered with measurable outcomes. This leader will supervise program directors, collaborate with the Senior Director of Business Development and Workforce Partnerships, manage large-scale contracts, and drive continuous improvement across all workforce development operations.

Qualifications

Required:

• Bachelor’s degree in public administration, Education, Social Work or related field.
• Minimum 8–10 years of progressive leadership experience in workforce development, human services, or nonprofit program management.
• Deep understanding of WIOA, DYCD workforce systems, and employment/training best practices.
• Proven ability to lead teams, manage complex operations, and seamlessly meet outcome deliverables in a mission-driven environment.

Preferred:

• Master’s degree in a related field.
• Experience managing government-funded programs (e.g., HRA, CWE, WIOA, TANF, CDBG, etc.).
• Familiarity with data systems such as Eccovia, Salesforce, YEPS, DYCD CONNECT, or similar platforms.
• Bilingual (Spanish, Mandarin, or other languages spoken in the service area) is a plus.

Key Competencies

• Strategic and operational leadership
• Program design and evaluation
• Budgeting and contract oversight
• Data-driven decision making
• Relationship and partnership management
• Equity-centered leadership

Key Responsibilities

Strategic Leadership & Vision

• Provide management and support for the directors overseeing English for Speakers of Other Languages (ESOL) and Adult Basic Education programs, as well as Job Essentials Training, Jobs Plus, and Youth Employment initiatives.
• Lead the development and execution of a comprehensive workforce development strategy aligned with organizational goals.
• Identify emerging trends, labor market shifts, and funding opportunities to evolve programming accordingly.
• Provide high-level thought partnership to the executive team on workforce innovation and policy.

Program & Operations Management

• Oversee day-to-day operations of all workforce development programs, including adult training, youth employment, apprenticeship, and sector-specific initiatives.
• Ensure program design, implementation, and evaluation are efficient, high-impact, and aligned with performance metrics.
• Direct a team of program managers and operations staff, fostering a culture of accountability and collaboration.

Performance & Quality Improvement

• Develop and monitor program KPIs, dashboards, and reporting systems for internal tracking and external compliance.
• Lead data-informed decision-making and implement continuous quality improvement frameworks.
• Ensure compliance with federal, state, and local workforce regulations and funder requirements.

Partnership & Stakeholder Engagement

• Cultivate and maintain relationships with workforce boards, funders, government agencies, employers, educational institutions, and community partners.
• Represent the organization in coalitions, convenings, and public forums to elevate our workforce mission.

Budget & Contract Management

• Oversee multi-million dollar program budgets, including public and private funding streams.
• Ensure fiscal accountability, contract compliance, and timely reporting to funders.
• Collaborate with finance and development teams to support grant writing, budget planning, and resource development.

Essential Physical Job Functions:

• Ability to work onsite in the Lower East Side