Deputy Director

Boston; Boston (MA); On-site; USD 110,000 - 170,000; Full time

Job summary

The City of Boston seeks a Deputy Director for the Department of Youth Employment and Opportunity, leading strategic and operational efforts to expand access to youth employment, workforce readiness, and civic engagement across Boston’s youth programs.

The role drives program management, financial oversight, and cross‑department collaboration, guiding change initiatives and ensuring impactful, equitable outcomes for Boston’s youth. Evening/weekend participation may be required.

Qualifications

• Four years in a senior leadership role in public sector/nonprofit
• Bachelor's degree required; Master's preferred in related fields
• Experience in operations, change management, youth development, finance, and administration
• Ability to collaborate with executive leadership and external partners
• Strong communication, problem-solving, and ability to lead diverse teams

Responsibilities

• Oversee strategic management and leadership across programs and staff
• Oversee operations, systems, and financial management for the department
• Support department investments in systems, staffing, programs, and budgets
• Prepare reports for Mayor's Office and city officials
• Lead coordination of grants, initiatives, and citywide youth employment programs

Skills

Leadership

Strategic Planning

Operations

Budgeting

Grant Management

Staff Development

Communication

Bilingual

Education

Bachelor's degree

Master's degree preferred

Tools

HR systems

Finance systems

Learning management

Job description

Under the direction of the Executive Director of the Department of Youth Employment and Opportunity, the Deputy Director is responsible for leading the department to be an organization that maximizes its external impact while focusing on internal effectiveness and efficiency. This role will support the strategic, operational, and financial responsibilities of the department by overseeing the buildout and optimization of internal systems, processes, organizational structure, and impact evaluation – with the goal of increasing access and opportunities for youth across youth employment, workforce and career readiness, and civic engagement and outreach programs, services, and initiatives.

The Deputy Director will serve as a critical member of the YEO Leadership team, and alongside the Department Executive Director will manage strategy and execution across all program teams & services. This role will also lead efforts to implement new initiatives for the department.

The position is designed for an individual who embodies a genuine passion for the department's mission of employing, developing, and engaging Boston youth by amplifying youth voices and bridging opportunities for personal and professional growth.

Strategic Management and Leadership:

• Oversees the department's general personnel and staff teams (including interns and indirect reports) and provides day-to-day leadership to support productivity, performance, and development of all.
• Oversees the department's core programmatic functions, including but not limited to:
  • Employment (youth recruitment, onboarding, and payroll processes)
  • Grant (multi-phase planning and implementation of the SuccessLink Grant process that serves over 230 partners annually across City departments and local nonprofits)
  • Communication, Engagement & Outreach (citywide youth jobs fair and other events, partnership management, and other related efforts)
  • Career-readiness (curriculum development and workshop administration)
• Serves as key thought partner and advisor alongside the Department Director to support the implementation of strategic goals, recommendations, team management, and ensuring innovative approaches and best practices are incorporated into the department's work that promote youth development.
• Manages and supervises direct reports for all program operations.
• Drives the impact, communication, and development work of the department.

Operational, Systems, and Finance Management:

• Develops & incorporates process improvement techniques into program operations and functions.
• Leads the implementation of new department investments around systems, staffing, programs, etc.
• Supports the annual budget and planning process with the Department Director and Grant & Budget Manager.
• Prepares weekly and quarterly reports and materials to share across the Mayor's Office, Human Services cabinet, and associated city offices.
• Supports the Grant & Budget Manager to build out financial, grant, and budget management systems.
• Oversees the analysis of current programs & initiatives to identify gaps and opportunities for growth.
• Co-manages staff performance management, training, and professional development across the department.

Programs and Special Initiatives:

• Leads change management initiatives to improve organizational effectiveness, specifically within the scope of the SuccessLink program.
• Oversees emerging department programs, events, services, and special projects and manages strategic alignment of proposed initiatives.
• Supports the department's grant funding initiatives to nonprofits and helps manage grant coordination, resource development, and alignment.
• Provides leadership of citywide events alongside the Engagement & Outreach team.
• Supports oversight of SYEP Evaluation and Impact Projects and leads and supports citywide youth jobs stakeholder priorities to improve job quality and align youth workforce development efforts across Boston's Youth Employment Providers - Boston PIC, ABCD, John Hancock MLK Scholars, and Youth Option Unlimited (YOU).

General:

• Ensures appropriate technical assistance is offered to all stakeholders and constituents.
• As needed, supports and participates in general youth employment activities, events, and special projects & represents the department.
• Performs related work as determined by the Director of YEO and/or delegate.
• Performs related work as required.

• Four (4) years of experience, or equivalent part-time professional experience working in a senior leadership position within the public sector, nonprofit, or with youth service providers in an administrative capacity, is required.
• Bachelor's degree required, and may substitute for two (2) years of required experience; Master's degree preferred in education, and may substitute for three (3) years of experience, organizational leadership, public administration, or related fields.
• Three to four (3-4) years of professional experience with operations, change management, youth development, nonprofit leadership, finance, and administration.
• Ability to collaborate with executive leadership, peers, and internal and external partners at the local, state, and federal levels.
• Understanding of youth-centered, workforce readiness, and/or civic engagement impact-centered program design and evaluation.
• Experience managing staff and ability to lead, develop, and collaborate with a diverse team.
• Strong communication, clear thinking, and problem-solving.
• Ability to work in a fast-paced environment, take initiative, manage change, adapt to the changing demands of the department, and drive forward the department's strategies and goals.
• Strong time-management and ability to work on multiple projects simultaneously, while maintaining attention to detail required.
• Proficiency with project management systems, HR and finance management, and learning management platforms.
• Demonstrated ability to communicate effectively in person, orally, and in writing with a diverse range of people, including constituents, staff, partners, funders, and city personnel.
• Demonstrated ability to work with limited direct supervision and perform assigned duties in an accurate, timely, and professional manner.
• Seeking a bilingual candidate (Spanish, Haitian Creole, Cape Verdean Creole, Chinese, and Vietnamese).

Must be able to attend evening and weekend meetings or events as required.

C.O.R.I. CHECK REQUIRED

S.O.R.I. CHECK REQUIRED

BOSTON RESIDENCY REQUIRED

Terms:

Union/Salary Plan/Grade: Non-Union/MM2-9

Hours per week: 35