Job ID: 60348

Job Category: Community & Emergency Services

Division & Section: Toronto Shelter & Support Services, Outreach and Access

Work Location: Metro Hall, 55 John St. Toronto

Job Type & Duration: Full-time, Permanent

Salary Range: $150,823.40-$177,213.40, PSG #TM0382, Wage grade 10

Ideal Hiring Zone: $179,443-$194,554

Shift Information: Monday to Friday, 7 Hours per day, 35 Hours per week

Affiliation: Non-Union

Number of Positions Open: 1

Posting Period: 22-Dec-2025 to 12-Jan-2026

An exciting opportunity to draw on best practices and join a team that is focused on transforming services for people who are experiencing sheltered and unsheltered homelessness in Toronto to achieve better housing outcomes.

The Director, Homelessness Initiatives and Prevention Services (Outreach and Access), will drive the mandate for access to shelter services, street outreach and encampment office services. An integral part of this role will be to direct homelessness initiatives, including City and community non-profit operated shelter, 24-hour respite, 24-hour and street outreach services, including case management services, and centralized intakes, as we focus on the stability of the sector and implementing a performance-based housing outcome-focused shelter and outreach system. The Outreach and Access section delivers, coordinates, and oversees an integrated system of direct services for individuals and communities impacted by homelessness.

Reporting to the General Manager of Toronto Shelter and Support Services Division, the Director, Homelessness Initiatives and Prevention(Outreach and Access) is accountable for the oversight of service system management of a shared shelter system that has experienced unprecedented demand, providing over 9000 shelter beds. In this role, you will provide executive leadership oversight and strategic decision-making, and direction on the City’s encampment response. Ensuring a successful coordinated, multi-sectoral approach to supporting individuals experiencing homelessness with complex needs, in collaboration with other relevant City Divisions, health care partners and community partners.

Toronto Shelter and Support Services is committed to working with Indigenous partners and communities towards reconciliation, supporting Black staff and clients and working within the principles of Equity, Diversity, and Inclusion to support diverse communities

Strategic orientation, continuous improvement and change

• Lead the continuous improvement of the Division's performance through analysis and the development and implementation of sound management practices and procedures, and by providing staff with the direction, guidance, processes and tools they need to increase efficiencies and improve effectiveness
• Lead and oversee a complex and robust service system, including outreach, shelter and support services to people experiencing homelessness and contract management for purchase of service programs.
• Develop and monitor an operating budget of over $50 million and ensure the effective, efficient use of City funding and City accountability for funding from provincial and federal governments through proactive negotiations and financial and program reporting
• Partner with other sections in the Division, all levels of government, community agencies and partners, City and external stakeholders to ensure integrated, client-focused housing services to address homelessness.
• Build, lead and motivate a diverse union and non-union workforce of approximately 500 staff within a 24/7/365 operation. Welcome different perspectives and optimizing creativity while ensuring effective teamwork, providing resolution to controversial labour relations issues, ensuring high standards of work quality and organizational performance, and encouraging continuous learning and innovation
• Participate actively in complex organizational and change management initiatives and in creating a workplace that supports and enables a high level of individual and organizational performance.
• Provide and encourage opportunities for intellectual growth, creative teamwork and professional accountability.

Customer focus and collaborative partnerships in a diverse environment

• Provides leadership and establishes partnerships with clients, external consultants, non-profit groups, members of Council, public, unions, Provincial and Federal government officials, etc. to address and resolve conflicting demands and problems from various stakeholders and foster effective partnerships while balancing corporate interests
• Establish an inclusive work environment by ensuring that policies, programs, resource or budget allocations, and systems are free from systemic, attitudinal or physical barriers to produce equitable results
• Integrate population diversity considerations in decisions, and assess their impact when planning, implementing, adapting and evaluating public programs, policies, services, systems and budgets.

Key Qualifications

• University Degree or College Diploma in a relevant discipline pertinent to the job function, or an equivalent combination of education and relevant management experience
• Extensive experience leading, managing and motivating a diverse workforce
• Extensive organizational and change management experience, utilizing effective management strategies and action planning to facilitate service delivery improvements
• Considerable financial management experience in developing, recommending and administering a budget
• Well-developed communication skills and an ability to inspire and mobilize people by developing and maintaining strong relationships, within staff, committees, politicians, peers and community leaders
• Advanced strategic, analytical and conceptual thinking skills with the capacity to understand complex operating and policy issues, evaluation frameworks, performance measures, program inter­ relationships and the potential consequences of intended policy action
• Knowledge of relevant employment legislation, including Employment Standards Act, Human Rights Act, Occupational Health & Safety Act etc
• Experience leading a Human Services organization will be an asset, in addition to an understanding of anti-oppression principles and practice
• Experience working in a unionized environment is a strong asset
• Extensive experience building and sustaining highly effective relationships and partnerships

Please Note

• Selected candidates may be required to provide a current Police Reference Check as a condition of employment for this position.
• For more information on our Programs and Services, please visit the City's website at: http://www.toronto.ca/housing

Equity, Diversity and Inclusion The City is an equal opportunity employer, dedicated to creating a workplace culture of inclusiveness that reflects the diverse residents that we serve. Learn more about the City’s commitment to employment equity.

Accommodation The City of Toronto is committed to creating an accessible and inclusive organization. We are committed to providing barrier-free and accessible employment practices in compliance with the Accessibility for Ontarians with Disabilities Act (AODA). Should you require Code-protected accommodation through any stage of the recruitment process, please make them known when contacted and we will work with you to meet your needs. Disability-related accommodation during the application process is available upon request. Learn more about the City’s Hiring Policies and Accommodation Process.