City of Boston

Executive Director

Req ID
Youth Employment & Opportunity
Regular Full-Time
YEE Office
Posting End Date
Contact Email


Under the direction of the Chief and Deputy Chief of the Worker Empowerment Cabinet, the Executive Director of the Office of Youth Employment & Opportunity (YEO) will oversee the mission, goal-setting, program design and delivery for both year-round and summer employment for the Mayor and the City of Boston.  This position is a department head level, senior leader in the Mayor’s administration responsible for essential youth serving programs for the City of Boston.


The Executive Director will oversee, manage, develop, and expand major youth-serving initiatives that are core to the Mayor’s agenda to provide Boston’s youth with employment and training opportunities key to positioning them for career success. These programs include the Mayor’s school-year and summer jobs program which places thousands of Boston youth in jobs annually and makes grants to support over 100 nonprofits and programs. It also includes the Workforce and career development programs to ensure youth are developing skills necessary to be ready for future career and educational experiences.  


Core responsibilities will include, but are not limited to engage city and community partners in the design and implementation of the employment programs (e.g. outreach, employer engagement and youth onboarding and hiring) manage a dynamic staff and volunteer team to document progress towards goal attainment, implement an effective and innovative outreach, marketing and communications plan to fully engage youth, community partners and employers, and evaluate the program for process improvement.  The Executive Director will also develop and monitor budgets, grants and other funding sources for successful fiscal compliance.


The Worker Empowerment Cabinet mission is creating a safe, healthy, and climate resilient city for Boston workers. The cabinet aims to advance the well-being of Boston workers in the public and private sectors by;

  • setting the City’s future policy and vision for workers
  • regulating, overseeing, and improving workplace conditions and health for workers, and;
  • expanding economic opportunities for workers through quality jobs, skills training, and career pipelines.

The Office of Youth Employment & Opportunity exists to employ, develop, and engage Boston's youth, by; exposing youth to the workforce, and bridging opportunities for personal and professional growth. YEO envisions a future where youth are educated, equipped, and empowered to transition successfully into adulthood. 


  • Keep abreast of research and evaluation trends on meaningful youth development and employment locally and nationally to develop policies, legislations, and best practices in the field.
  • Represent the Mayor, the Chief and the Worker Empowerment Cabinet at youth, community and industry meetings and events.
  • Engage employers, including community non profit partners, private sector employers, and small businesses in the development of career pathways, job readiness, and work-based competencies for Boston’s youth.
  • Build strong partnerships within the City of Boston’s agencies, community partners, post-secondary education for the selection, hiring, onboarding of Boston youth.
  • Design and implement industry-based employment programs to creatively engage youth during the summer employment.
  • Design and manage a youth hiring campaign to increase private sector employers and small businesses.
  • Assess programmatic, administrative and fiscal work flows to effectively identify skills gaps and manage a diverse staff team.
  • Design and implement an innovative communication campaign for recruitment, hiring and promoting meaningful youth employment programs for the City.
  • Recruit, train and retain a talented staff team to encourage collective action-oriented solutions and a positive working environment.
  • Serve as the external face of the division by building and managing relationships with strategic community partners, the philanthropic community, and the media.
  • Provide fiscal oversight for the unit, including developing and implementing budgets and managing and reporting assets, revenue, and expenditures, developing standard operating procedures for compliance (e.g. payroll verification, grants and contract compliance, and other budgetary tasks).
  • Manage  and oversee the day to day business functions including payroll processing and hiring of the division’s staff.
  • Oversee department strategic and operational functions, including strategic planning, office operations, IT and technical systems, etc. 
  • Prepare weekly and quarterly reports and materials to share across the Mayor's Office, Worker Empowerment cabinet and associated city offices. 
  • Support oversight of SYEP Evaluation and Impact Projects and leading and supporting 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).
  • Ensures appropriate technical assistance is offered to all stakeholders and constituents.
  • As needed, supports and participates in general cabinet activities, events and special projects.
  • Perform related work as determined by the Deputy Chiefs and the Chief.

Minimum Entrance Qualifications:

  • At least five (5) years of full-time, or equivalent part-time, professional experience working in a leadership position within the public sector, private sector or with youth service providers, programs and activities with an emphasis on outreach and program coordination, of which two (2) years must have been in a supervisory or managerial capacity. 
  • A bachelor’s degree in business administration, education, organizational leadership, public administration, social services or in related fields is strongly preferred and may be substituted for two (2) years of the required experience. There is no substitute for supervisory experience.
  • Experience managing staff and ability to lead, develop and collaborate with a team.
  • Ability to collaborate with executive leadership, internal and external partners at the local, state and federal level.
  • Proficiency with Google Suite, MS Office (Word, Excel, PowerPoint, Publisher) and Social Media required. Planning, organization, and project management skills required.
  • Intermediate proficiency with project management systems, HR and finance management and learning management platforms
  • 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 interpersonal, facilitation and listening skills required.
  • Ability to work on multiple projects simultaneously, while maintaining attention to detail required.
  • Demonstrated ability to communicate effectively orally and in writing with a diverse range of people including citizens, staff, and City personnel.
  • Demonstrated ability to establish and maintain effective working relationships with subordinates, peers, superiors, and public and private representatives.
  • Demonstrated ability to work with limited direct supervision and accurately perform assigned duties in an accurate, timely and professional manner.
  • Ability to exercise good judgment and focus on detail in a fast paced environment as required by the job.
  • Must be able to attend evening and weekend meetings or events as required.
  • Bilingual candidates recommended.


C.O.R.I. Check Required. S.O.R.I. Check Required
Boston Residency Required

Union/Salary Plan/Grade: Cabinet Department Head (CDH)
Hours Per Week: 35


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