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, JHST plays an important role in helping people navigate some of the most complex moments in their lives.
JHST is now seeking an Executive Director to lead the organization through its next chapter by strengthening its operational foundation, supporting its people, and 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, JHST must balance mission-driven service delivery with strong operational leadership, financial stewardship, and organizational accountability.
The next Executive Director will provide the leadership needed to strengthen internal systems and management capacity, ensure programs remain effective and responsive, maintain strong relationships with funders and justice-sector partners, and position the organization for continued stability and impact.
This role requires a leader who understands that meaningful social impact depends on both compassion and operational discipline.
The Opportunity
The Executive Director serves as JHST’s chief executive, with overall responsibility for organizational leadership, operations, financial stewardship, workforce leadership, program performance, and external relationships.
Working closely with the Board of Directors under a policy governance (Carver) model, the Executive Director operates within Board-established strategic direction and policies while holding responsibility and accountability for the organization’s operational leadership and decision-making.
The Executive Director leads a multidisciplinary organization delivering justice reintegration and housing supports and ensures that people, programs, resources, and partnerships are aligned to achieve meaningful outcomes.
The role also provides an opportunity to contribute to the broader conversation about how reintegration and housing supports are delivered within Toronto’s justice and community services ecosystem.
Why Join the JHST
JHST offers the opportunity to lead an established organization whose work contributes directly to community stability, successful reintegration, and second chances.
The Executive Director will work alongside a committed team, an engaged Board of Directors, and justice and community-sector partners dedicated to ensuring individuals have access to the supports they need to rebuild their lives.
For a leader motivated by meaningful social impact, this is an opportunity to strengthen an important organization and guide its next stage of stability, sustainability, and impact.
Key Responsibilities
Organizational Leadership
· Provide clear, accountable leadership aligned with JHST’s mission, values, and strategic direction.
· Build, develop, and support a strong management team accountable for program delivery, operational performance, and staff leadership.
· Translate organizational priorities into clear plans, expectations, and accountabilities across the organization.
· Foster a workplace culture where employees feel heard, respected, and supported while ensuring clear direction, accountability, and timely decision-making.
· Promote trauma-informed and inclusive leadership practices in interactions with staff and the communities JHST serves.
· Navigate complex organizational and workforce challenges with sound judgment while supporting staff safety and well-being.
· Provide steady, decisive leadership during complex, sensitive, or high-risk situations.
Program Impact and Service Delivery
· Provide executive oversight of programs supporting justice-involved individuals, including reintegration and housing initiatives.
· Ensure services are safe, effective, responsive, and aligned with JHST’s mission and contractual obligations.
· Ensure programs remain responsive to the needs of communities disproportionately impacted by the justice system.
· Strengthen the measurement, evaluation, and reporting of program outcomes and organizational impact.
· Establish and monitor meaningful key performance indicators across program delivery, client outcomes, and organizational performance.
· Identify and manage operational and program risks and ensure appropriate systems of oversight and accountability are in place.
Financial Leadership and Sustainability
· Provide strong financial leadership and stewardship across the organization.
· Lead annual budgeting and financial planning and ensure effective financial controls, monitoring, and accountability.
· Ensure program and financial reporting meet funder, contractual, regulatory, and organizational requirements.
· Maintain fiscal discipline and work with the Board and leadership team to support a balanced and sustainable financial position.
· Identify opportunities to diversify revenue and strengthen JHST’s long-term financial sustainability.
· Oversee the organization’s grant funding strategy, including identifying opportunities, supporting strong proposals, and ensuring compliance with funding requirements.
Labor Relations and Workforce Leadership
· Provide effective leadership within a unionized workplace.
· Build and maintain constructive labour-management relationships.
· Lead and participate in collective bargaining, including organizational preparation and mandate development.
· Oversee significant employee and labour relations matters with fairness, consistency, sound judgment, and appropriate regard for organizational risk.
· Ensure effective people practices support employee engagement, accountability, organizational effectiveness, and service delivery.
External Leadership and Partnerships
· Build and maintain strong relationships with government funders, justice-sector partners, community organizations, and other key stakeholders.
· Represent JHST publicly and serve as the organization’s primary spokesperson on local matters.
· Strengthen JHST’s credibility, visibility, and relationships across Toronto’s justice and social services sectors.
· Identify opportunities for collaboration, partnership, advocacy, and sector leadership that advance JHST’s mission.
Governance and Board Partnership
· Build a strong, transparent, and effective working relationship with the Board of Directors.
· Support the Board in advancing JHST’s strategic direction and fulfilling its governance responsibilities.
· Provide timely, transparent reporting on organizational performance, finances, risks, opportunities, and emerging issues.
· Operate effectively within JHST’s policy governance framework, maintaining clear accountability and appropriate boundaries between governance and management.
· Provide the Board with the information, analysis, and advice required to support sound governance and informed decision-making.
The Leader We Are Looking For
You are an experienced senior leader who combines mission commitment with operational discipline. You are comfortable leading through complexity, making difficult decisions when required, and building trust and accountability across an organization.
You bring:
· Progressive senior leadership experience in the nonprofit, public, justice, social services, or a similarly complex mission-driven environment.
· Demonstrated experience leading people, programs, operations, and organizational change.
· Strong financial acumen and demonstrated experience with budgeting, financial oversight, risk management, and resource allocation.
· Experience strengthening organizational systems, management practices, and operational accountability.
· Experience managing complex workforce and employee relations matters; experience within a unionized environment is strongly preferred.
· Experience working with and reporting to a Board of Directors.
· Demonstrated ability to build productive relationships with government, funders, community partners, and other stakeholders.
· Strong judgment, emotional intelligence, conflict resolution, and decision-making capabilities.
· Excellent communication skills and the ability to build credibility and trust with diverse stakeholders.
· A demonstrated commitment to equity, inclusion, and trauma-informed leadership.
Experience working within the justice sector or with justice-involved populations, reintegration services, supportive housing, or related community-based programs is considered a strong asset.
Above all, JHST is seeking a leader who can balance people, purpose, performance, and sustainability. Someone who can listen and build trust while also providing the clarity, accountability, and decisive leadership required of a chief executive.
How to Apply
Interested candidates are invited to submit a resume and cover letter outlining their qualifications and experience. Applications will be accepted until September 16, 2026. They will be reviewed as they are received, and early applications are encouraged.
We offer a competitive executive compensation package, including a starting salary of $130,000-$160,000 per year, with placement within the range based on the successful candidate’s experience, qualifications, and leadership expertise, along with a comprehensive benefits program.
The John Howard Society of Toronto is committed to an inclusive, accessible, and equitable recruitment process. Accommodations are available upon request throughout the recruitment process.
Our recruitment process is led by people. AI may be used for administrative support only and is not used to evaluate candidates or make hiring decisions.
We thank all applicants for their interest. Only candidates selected for an interview will be contacted.
Pay: $130,000.00-$160,000.00 per year
Benefits:
- Dental care
- Extended health care
- Life insurance
- Paid time off
Application question(s):
- Do you have senior leadership experience in the nonprofit, public, justice, or social services sector? If yes, please specify the sector and the number of years of experience.
- Do you have experience with financial planning, forecasting, and reporting at an organizational level?
- Do you have experience managing employee relations within a unionized environment?
Work Location: In person
