Director of Workforce Development

St. Francis House (SFH) is the Commonwealth’s largest day shelter for adults experiencing homelessness and poverty, serving up to 600 individuals each day, year-round, across two downtown Boston locations. Alongside meals, clothing, showers, and other basic necessities, SFH offers an on-site medical clinic, behavioral health and recovery services, permanent supportive housing, and workforce development, all guided by a person-centered, recovery-oriented, and trauma-informed Philosophy of Care.

For more than 30 years, SFH’s commitment to Workforce Development has helped guests facing homelessness and other significant barriers to employment increase income, build skills, and move toward greater stability. Today, the department is anchored by the Sullivan Family Moving Ahead Program (MAP), a structured 14-week employment readiness and life-skills program, and Employment Services, which provides individualized job search, training, education, and wellness and life skills support. An on-site boutique also provides guests with professional attire. Participants come to these programs from shelters, recovery housing, incarceration, and other life circumstances as they build or rebuild their careers.

SFH is seeking an experienced, steady, and forward-looking Director of Workforce Development to lead a $1.4 million operation and an 11-member team as the department strengthens coordination across programs and adapts to a changing job market. Reporting to the Vice President of Programs & Services, the Director holds a hands-on, highly visible role with responsibility for public contracts and partnerships across Boston’s workforce, recovery, and human-services networks. Priorities include establishing clear goals and measures of success and deepening employer and community relationships. SFH is awaiting decisions on new funding that would expand its programming, and the next Director would help shape that growth.

Ideal Candidate Portrait

• A seasoned workforce development leader committed to SFH’s Philosophy of Care and to helping people achieve lasting economic stability.
• A leadership style that is decisive without being rigid, collaborative without avoiding difficult calls, and confident without losing humility.
• A demonstrated ability to lead in a hands-on service environment, model best practices, and navigate complex or sensitive situations with sound judgment and composure.
• A data-informed approach that values measurable outcomes while recognizing the individual stories behind the numbers.

Primary Responsibilities

• Lead the department’s Workforce Development strategy across MAP and Employment Services, aligning programs around shared goals, and ensuring effective coordination and accountability.
• Lead, coach, and develop a multi-disciplinary team, including direct supervision of MAP and Employment Services Managers, Wellness and Life Skills Coach, and Program Assistant.
• Oversee a $1.4 million budget that braids federal, state, city, and philanthropic funding (including DOL, HUD Continuum of Care, WIOA, and the City of Boston), with responsibility for compliance, reporting, renewals, and quality assurance, working closely with SFH’s finance and contracts teams.
• Serve as a member of SFH's leadership team, contributing to organization-wide planning and decision-making while maintaining a visible, hands-on presence in program operations.
• Establish clear performance goals and measures for employment, income, retention, program quality, and participant outcomes, and use the data to drive continuous improvement.
• Build and sustain strategic relationships with training providers, recovery and housing nonprofits, funders, and other community partners (e.g., MassHire, Boston Private Industry Council, City of Boston), and identify opportunities for collaboration, funding, and program models.
• Deepen employer engagement and develop workforce pathways that respond to labor market demand and lead to sustainable employment and career advancement.
• Ensure programs reflect SFH’s person-centered, recovery-oriented, and trauma-informed Philosophy of Care.

Qualifications

• At least five years of progressive leadership experience in workforce development, with demonstrated success leading established programs, managing multidisciplinary teams, and driving measurable outcomes in a complex direct-service environment.
• Strong knowledge of employment readiness, training, placement, and retention; familiarity with WIOA, MassHire, career centers, and related workforce systems strongly preferred.
• Strong people leadership skills, including coaching and developing staff, encouraging teamwork, setting clear expectations, building trust, and fostering accountability.
• Experience working with people facing homelessness or other significant barriers to employment and integrating supportive services, such as behavioral health, recovery, and housing, into employment programs.
• Experience with budget management, public contracts, funders, data, and performance measurement.
• Bachelor’s degree in social work, public health, public administration, vocational rehabilitation, or a related field; master’s degree preferred.

Annual compensation: $106,000–$117,000, commensurate with experience. Competitive benefits package with generous paid time off and retirement benefits. Hybrid work schedule.

St. Francis House is an Equal Employment Opportunity Employer committed to fostering a diverse and inclusive workforce. SFH welcomes candidates with lived experience and those who have faced historic barriers to competitive employment.

This is a retained executive search conducted by Exceptional Executive Search.

To apply or inquire, contact View email address on click.appcast.io.