Executive Director

Justice, Reintegration, and Community Stability

Some organizations change lives quietly.

For decades, the John Howard Society of Toronto (“JHST”) has supported individuals involved in the justice system as they rebuild stability, secure housing, reconnect with supports, and move toward a different future.

Working at the intersection of justice, housing, and social services in Toronto, the organization plays an important role in helping people navigate some of the most complex moments in their lives.

The JHST is now seeking an Executive Director to lead the organization through its next chapter by strengthening its operational foundation while ensuring the long-term sustainability and impact of its programs.

Why This Role Matters Now

Demand for reintegration and housing supports continues to grow while justice-sector priorities and funding environments evolve.

Like many nonprofits operating within complex systems, the JHST must balance mission-driven service delivery with strong operational leadership and financial stewardship.

The organization is entering a period where strengthening internal systems, leadership capacity, and operational consistency will be essential to supporting long-term program success.

The next Executive Director will ensure programs remain effective, relationships with funders and justice partners remain strong, and the organization is positioned for continued stability and impact.

This role requires a leader who understands that meaningful social impact requires both compassion and operational discipline.

The Opportunity

The Executive Director serves as the organization’s chief executive and is responsible for overall leadership, operations, financial stewardship, and external relationships.

The role ensures the organization remains mission-driven, operationally strong, and financially sustainable while delivering programs that support justice-involved individuals across Toronto.

Working closely with the Board of Directors under a policy governance (Carver) model, the Executive Director provides organizational leadership while maintaining alignment with Board-established strategic direction and policies.

Within this governance framework, the Executive Director holds responsibility for operational leadership and operational decision-making across the organization.

The role oversees a multidisciplinary team delivering programs across justice reintegration and housing support while managing the operational, financial, and partnership responsibilities of a complex community organization.

The Executive Director will also play an important role in shaping how reintegration and housing supports are delivered within Toronto’s broader justice and community services ecosystem.

Why Join the JHST

The JHST offers the opportunity to lead an organization whose work contributes directly to community stability, reintegration, and second chances.

The Executive Director will work alongside a committed team, an engaged Board of Directors, and justice-sector partners dedicated to ensuring individuals have access to the support needed to rebuild their lives.

For leaders motivated by meaningful social impact, the role offers the opportunity to guide an established organization through its next stage of stability, growth, and community impact.

Key Responsibilities

Organizational Leadership

• Provide clear, accountable organizational leadership aligned with the organization’s mission and strategic direction.
• Develop and support a strong management team responsible for program delivery, operational performance, and staff leadership.
• Set clear expectations and ensure alignment across teams so staff work effectively toward shared organizational goals.
• Foster a workplace culture where staff feel heard, respected and supported while providing clear direction and timely decision-making.
• Ensure organizational priorities are translated into clear plans and that teams are supported and held accountable for delivering results.
• Promote trauma-informed and inclusive leadership practices that support respectful engagement with staff and the communities served.
• Navigate complex organizational and workforce challenges with sound judgment while maintaining accountability, staff safety and well-being.
• Provide steady leadership during complex or high-risk situations, ensuring appropriate response and clear communication.

Program Impact and Service Delivery

• Oversee programs supporting individuals involved in the justice system, including reintegration and housing initiatives.
• Ensure services are delivered safely, effectively, and in alignment with the organization’s mission.
• Ensure programs are responsive to the needs of communities disproportionately impacted by the justice system.
• Strengthen outcome measurement and reporting to demonstrate program impact.
• Ensure the organization establishes, tracks and achieves key performance indicators across program delivery, client outcomes and organizational impact.
• Monitor operational risks and ensure appropriate oversight across programs.

Financial Leadership and Sustainability

• Oversee financial management and accountability across the organization.
• Ensure program and financial reporting meet funder requirements.
• Maintain a balanced budget and strong financial controls.
• Identify opportunities to strengthen financial sustainability and diversify revenue.
• Oversee the organization’s grant funding strategy, including identifying funding opportunities, supporting the development of strong proposals, and ensuring compliance with grant requirements.

Labor Relations and Workforce Leadership

• Lead effectively in a unionized environment.
• Support constructive labour-management relationships.
• Lead, prepare for and participate in collective bargaining processes.
• Address employee relations matters with fairness, clarity, and sound judgment.

External Leadership and Partnerships

• Maintain strong relationships with government funders, justice partners, and community organizations.
• Represent the organization publicly and serve as its primary spokesperson on local matters.
• Collaborate with sector partners on justice and reintegration initiatives.
• Build credibility and trust across Toronto’s justice and social services sectors.

Governance and Board Partnership

• Work closely with the Board to advance the organization’s strategic priorities.
• Provide transparent reporting on organizational performance, risks, and opportunities.
• Support the Board in fulfilling its governance responsibilities while maintaining clear boundaries between governance and management.

The Leader We Are Looking For

You bring:

• Senior leadership experience in the nonprofit, public, justice, or social services sector
• Demonstrated financial stewardship, with sound judgement in budgeting, risk management and resource allocation
• Strong operational management and strategic thinking capability
• Experience leading complex organizations, programs, and systems
• Experience managing workforce and employee relations issues, ideally within a unionized environment
• Experience working with or reporting to a Board of Directors
• The ability to lead change while building trust, accountability, and team alignment
• Sound judgment, emotional intelligence, and strong conflict resolution skills
• Excellent communication and relationship-building abilities
• A commitment to equity, inclusion, and trauma-informed leadership

Experience working with justice-involved populations, reintegration services, or housing programs is considered a strong asset.

We are looking for a leader comfortable navigating complexity, making difficult decisions when required, and building trust with staff, partners, and the communities we serve.

Our Commitment

The JHST is an equal opportunity employer dedicated to building an inclusive and accessible workplace. If you require accommodations during the hiring process, please let us know.

We recognize that great leaders come from diverse experiences. If this role excites you, even if you don’t meet every qualification, we encourage you to apply.

Salary Range: $130,000 - $150,000

How to Apply

Please submit your resume and cover letter to:   

In your cover letter, please tell us:

•       Why this role interests you

•       What excites you about the organization’s work

•       One example of leadership experience that has prepared you to guide an organization through complexity or change

We thank all applicants for their interest. Only those selected for an interview will be contacted.