Chief Executive Officer (CEO)

About Opportunity for Work & Learning (OWL)

OWL is a nonprofit organization dedicated to breaking barriers to employment for individuals with disabilities and individuals impacted by incarceration, poverty, and workforce displacement. Through supported employment, training, and wraparound services, OWL helps people regain economic independence, stability, and purpose.

OWL exists to serve people first, operations support the mission, not the other way around. OWL has a subsidiary called the Lexington Manufacturing Center (LMC), which is a for-profit arm that partially funds OWL’s operations and overhead.

 

Position Summary

Opportunity for Work & Learning (OWL) seeks a changemaker, a Chief Executive Officer (CEO), to lead the organization’s nonprofit mission focused on serving individuals with disabilities and individuals seeking a second chance through employment, training, and dignity of work.

This is a mission-first, community-centered CEO role, accountable for restoring leadership stability, strengthening programs, rebuilding trust, and positioning OWL for long-term sustainability, growth, and impact. This role is about people, programs, funding, community impact, and organizational leadership.

The CEO reports to the Board of Directors and is the public, operational, and strategic leader of the nonprofit.

 

Core Areas of Leadership

1. Mission & Community Impact Leadership

• Own and advance OWL’s mission of serving individuals with disabilities and second-chance populations
• Ensure programs directly translate to real employment outcomes, wage growth, and long-term stability
• Build strong partnerships with social service agencies, justice system partners, disability advocates, educators, and workforce organizations
• Serve as OWL’s chief ambassador in the community, advocating for inclusive employment

2. Financial Sustainability & Fund Development

• Own full nonprofit financial leadership: budgeting, cash flow, transparency, and audit readiness
• Lead all fundraising strategy: grants, public funding, philanthropy, corporate sponsorships
• Diversify revenue so OWL is not dependent on single-source funding
• Ensure every program is financially viable and mission-aligned
• Build long-term financial resilience

3. Manufacturing management and support

• Strengthen business development process
• Ensure LMC supports the OWL mission financially
• Continually improve manufacturing processes and increase ROI
• Ensure quality and safety across the organization

4. Organizational Stabilization & Growth

• Rebuild and stabilize internal operations following leadership transition
• Implement structure, discipline, accountability, and performance management
• Strengthen policies, procedures, HR systems, and compliance
• Build a reliable, high-performing leadership team
• Transition OWL from reactive to strategically led

5. Board & Governance Leadership

• Serve as the primary strategic partner to the Board of Directors
• Ensure strong governance, reporting discipline, and board engagement
• Translate board vision into executable strategy
• Operate with transparency, accountability, and trust

6. Talent, Culture & People Leadership

• Lead with empathy, clarity, and performance expectations
• Build a culture of dignity, professionalism, accountability, and compassion
• Prioritize staff development, retention, and leadership succession
• Foster a values-based workplace rooted in service and excellence

 

Qualifications

• Bachelor’s degree required, advanced degree in nonprofit management, public administration, social work, business, or related field preferred
• Minimum 7–10 years of proven leadership experience in:
• Nonprofit executive leadership
• Workforce development
• Disability services
• Reentry / second-chance employment
• Community-based organizations
• Grant-funded programs
• Proven experience in:
• Fund development and grant leadership
• Financial management is key
• Board partnership
• Organizational turnaround or growth
• Communication skills through writing and presenting
• Deep emotional intelligence and people-centered leadership
• Lean manufacturing experience and knowledge a plus

 

CEO Success Profile

The successful CEO will be:

• Financially disciplined
• Politically and socially savvy
• Comfortable in crisis
• Comfortable leading transformation
• Comfortable making hard decisions
• Equally credible with funders, staff, clients, and community leaders

 

The successful candidate will reshape the organization’s future and directly impact hundreds of lives each year.

 

Email your resume and cover letter to [email protected].  Interviews will begin in January and will continue until the position is filled.