The Director of Employment and Workforce Initiatives is responsible for designing, implementing, and overseeing comprehensive career exploration and workforce development programming for youth served by Heartshare St. Vincent’s Services. This role ensures that youth are meaningfully engaged in structured career readiness activities that prepare them for sustainable employment and long-term career success.

The Director supervises and provides strategic leadership to a team of Employment Specialists, ensuring the delivery of high-quality, individualized employment coaching and skill-building services. The team facilitates one-on-one employment coaching sessions, career assessments, job readiness workshops, and employment-themed activities focused on resume development, interview preparation, workplace professionalism, financial literacy, and career pathway exploration.

Additionally, the Director cultivates and maintains partnerships with internal program leaders. Is also responsible for maintaining accurate and timely employment data, tracking participant outcomes, and utilizing performance metrics to inform program design and continuous quality improvement. This role supports the Vice President of Youth Development and Community Programs by contributing data analysis, narrative reporting, and documentation for grant proposals, reports and compliance requirements.  

Primary Responsibilities and Essential Functions of Position:

• Supervise and support a team of up to six Employment Specialists.


• Design and facilitate career exploration workshops.


• Attend and complete all required Heartshare, ACS, Fair Futures, and career development trainings.


• Lead and manage any on-site internship programs (e.g., Mentored Internship Program).


• Coordinate and implement the Summer Youth Employment Program for Heartshare youth.


• Serve as Advisor to the American Dream Program Youth Council, ensuring consistent meetings and activities year-round.


• Support youth with applications for the ACS Career Choice Program and manage stipend reimbursements in collaboration with the Special Assistant.


• Assist youth in applying to vocational, certificate, and apprenticeship programs.


• Prepare and submit grant applications and reports.


• Monitor and track employment data using the Employment Tracker and Care4 platform; ensure timely documentation and completion of employment goals.


• Complete employment program related grant applications and reports in collaboration with the VP of Youth Development and Community Programs and the Development Team.


• Partner with the Director of Youth Development to co-lead team meetings and staff trainings.


• Oversee any on-site job readiness program(s) (e.g., YA WORC Work Learn and Grow, NYCHer and Career Connected Learning Opportunities from ACS), including enrollment and scheduling of program cycles.


• Help youth develop or refine their resumes and conduct career assessments.


• Meet with youth who are on a vocational pathway, or who have left college, to explore alternative post-secondary pathways and career paths in line with their interests and skills.


• Help youth apply to external programs, including vocational and workforce development programs (after speaking with their Coach).


• Meet with youth who are enrolled in college to do career planning and ensure all college seniors and college graduates secure employment


• Assists with job applications, when needed.


• Oversee and ensure the success of all employment and workforce related programming and initiatives.