Deputy Director

City of Boston; Boston (MA); On-site; USD 120,000 - 180,000; Full time

Benefits offered by this job

Retirement plan

Health insurance

Educational assistance

Salary information

Job summary

City of Boston is seeking a Deputy Director for the Department of Youth Employment and Opportunity to lead strategy, operations, and financial management. The role focuses on building systems, optimizing processes, and expanding access to youth programs citywide.

The incumbent will work with the Executive Director and lead program teams, including employment, grant, outreach, and career-readiness functions, while guiding evaluation and growth across initiatives in Boston's youth ecosystem.

Qualifications

• Four (4) years of senior leadership experience in public, nonprofit, or youth services administration.
• Bachelor's degree required; master's preferred can substitute years of experience.
• Three to four (3-4) years in operations, change management, nonprofit leadership, finance and administration.

Responsibilities

• Provide strategic leadership to maximize internal effectiveness and external impact.
• Oversee program operations, personnel, budgeting, reporting and grant management.
• Coordinate cross‑department collaboration and drive department initiatives.

Skills

Senior leadership

Operations management

Change management

Youth development

Nonprofit leadership

Finance administration

Project management

Education

Bachelor's degree

Master's degree preferred

Tools

Project management systems

HR and finance management

Learning management platforms

Job description

About the Department

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.

Position Duties

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.

Minimum Qualifications

• 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

Benefits

At the City of Boston, we provide our employees with a wide array of benefits and resources that foster both their professional and personal development. Our goal is to make City government a place where everyone is empowered to make a positive impact for the communities in which we live, work, and play.

For full-time positions, employees may be eligible for the following benefits depending on the nature of their employment and applicable Collective Bargaining Agreement (CBA) for the position. View the Collective Bargaining Agreements page to learn more.

Benefits Available to City Workers

• Retirement & Savings Opportunities: Membership in the Boston Retirement System (BRS), a benefit pension plan providing lifetime income to vested employees when they retire, along with deferred compensation options to help you build a secure future. Visit boston.gov/retirement to learn more.
• Health Insurance & Benefits: The City offers competitive medical, dental, and vision coverage, plus flexible spending (FSA), dependent care accounts, and life insurance for our employees. Visit boston.gov/insurance to learn more.
• Other Benefits: City employees enjoy a benefits package featuring paid time off and leave, subsidized transit (MBTA and Bluebikes), educational assistance, and employee wellness programs. Visit boston.gov/life-city-boston to learn more.
• Salary information: To view salary plans and understand how salaries work at the City of Boston, go to boston.gov/salary.

Part-time employees who are scheduled to work for 20 hours or more per week may also be eligible for benefits on a pro-rated basis. Please refer to the applicable Collective Bargaining Agreement (CBA) to learn more about any benefits available for this position.

If you have any questions about the benefits offered for this position, please contact the Office of Human Resources at 617-635-3370 or [e-mail].

Agency Information

Employer: City of Boston (MA)

Address: 1 City Hall Plaza, Room 612, Boston, Massachusetts, 02201

Phone: [phone]

Website: https://www.boston.gov