Title: Director of Program and Services
Location: 962 Bloor St West
Supervisor: Executive Director
Sistering is a multi-service agency which offers practical and emotional support to women and trans people facing a variety of challenging life circumstances, including poverty, homelessness, social isolation, mental health and trauma histories.
Our Vision
Sistering envisions a world where all women and trans people, in all our diversity, are valued; a world where we are safe and supported, treated with dignity, and given the respect we deserve. When opportunities are just and equitable, we can live life on our own terms.
Our Mission
Our goal is to create a safe, non-judgmental space for women and trans people who are socially isolated, poor, homeless or precariously housed. Guided by principles of Anti-Oppression and Anti-Racism, Sistering works to change the social conditions that endanger women and trans people’s welfare.
What We Do
Sistering’s programs include a low-barrier 24/7 Drop In, Housing and Case Support, Harm Reduction, Peer Outreach, On the Path to Employment and Spun Studio social enterprise, and individual and systemic advocacy.
How We Do It
Sistering operates on a trauma-informed and relationship-based model and our harm reduction philosophy is a core element of all the work we do: we are here to respond to participants’ needs, where they are at, in the moment, to support participants to learn how to reduce harm and/or increase safety. And we recognize that their lives have meaning and value.
POSITION SUMMARY:
Under the supervision of the Executive Director (ED), the Director of Programs and Services provides progressive and innovative leadership, strategic management and directs the Programs and Services Department. The Director of Programs and Services efficiently coordinates the strategic and operational functions of the department, to provide high quality programs and services to the community.
KEY RESPONSIBILITIES:
Leadership
- Develop and implement policies, programs, and services that align with Sistering’s vision and strategic plan
- Lead and coordinate services across programs, ensuring a seamless experience for participants
- Support and guide program managers in program-related activities
- Conduct trend and outcome analysis to assess and improve program effectiveness
- Lead the development of evidence-informed, innovative services that address the needs of Sistering’s target population
- Work closely with the Fund Development team to secure funding and advocate for program needs
- Foster and maintain a positive work culture that promotes job satisfaction, respect, and inclusion for staff and participants
- Establish and maintain relationships with key stakeholders, including government agencies, community partners, and advocacy groups
- Represent Sistering on external committees aligned with our mission and goals
- Provide leadership and support to staff and the Board in advocacy efforts
Program Direction
- Develop, monitor, and evaluate program operations to ensure alignment with organizational goals
- Prepare departmental work plans and oversee service delivery quality
- Conduct relevant research and program evaluations to ensure best practices
- Maintain accurate data collection, reporting, and analysis to inform decision-making and funding requirements
- Ensure programs and services comply with funders’ requirements, legislative standards, and best practices related to homelessness services
- Develop and oversee program budgets in collaboration with the Senior Leadership Team
- Monitor program expenditures, approve budgets, and adjust financial strategies as necessary
- Provide oversight and support for funding requests and reporting
- Maintain and update policies relevant to programs and services
- Lead emergency preparedness planning for programs and services
- Act as Executive Director in their absence, including liaising with the Board as needed
- Represent the organization in contract negotiations with the Union
- Ensure alignment with industry best practices through ongoing evaluation and quality improvement initiatives
Human Resources
- Recruit, select, and onboard program managers, supervisors, and staff
- Provide leadership, supervision, and performance management support
- Implement structured performance evaluations focused on individual growth and professional development
- Foster a learning culture with regular team meetings, training sessions, and mentorship opportunities
- Ensure compliance with data collection and quality assurance policies
- Lead program development and risk management initiatives to safeguard staff and participants
- Keep the Executive Director informed of critical operational issues
- Develop strategies for staff retention and workplace wellness initiatives
Advocacy and Community Engagement
- Strengthen partnerships with external agencies to enhance service delivery and collaboration
- Lead Sistering’s participation in coalitions and advocacy efforts
- Identify and pursue new funding opportunities in collaboration with the Executive Director and Fund Development team
- Advocate for policy changes that benefit marginalized communities and enhance service access
- Support Sistering’s role as a thought leader in the homelessness and social services sector
- Engage the Board in advocacy initiatives that support Sistering’s mission
QUALIFICATIONS AND SKILLS:
- Minimum 5 years’ experience in a senior management role within the health or human services sector
- Demonstrated success in policy development, program implementation, and systems building
- Experience working with government agencies, intergovernmental organizations, and non-profits
- Strong background in change management and project management
- Extensive knowledge of community resources, homelessness services, and harm reduction practices in Toronto
- Strong understanding of relevant legislation, including employment law, Occupational Health and Safety Act, and Ontario Human Rights Code
- Experience managing staff, budgets, and complex program implementations
- Proficiency in data analysis, reporting, and outcome measurement
- Excellent problem-solving, negotiation, and communication skills
- Ability to develop strategic partnerships and secure funding from diverse sources
- Experience leading teams through long-term, complex program implementations
- Knowledge of trauma-informed care principles and best practices
- Strong ability to navigate conflict resolution and crisis management scenarios
Education and Experience Requirements
- Master’s degree in social work, nursing, social health sciences, or a related field (preferred)
- Membership in good standing with a relevant professional regulatory body
- Certification in Project Management, Conflict Resolution, Proposal Writing, Quality Improvement, or Change Management (an asset)
- Experience working in non-profit, community-based settings
- Lived experience or deep understanding of issues related to homelessness, social isolation, and mental health is considered an asset
COMPENSATION:
- $100,000 - $110,000 annually
- Non -Unionized Role
-
Comprehensive Benefits Package including:
- Group health and dental benefits
- Defined benefit pension plan
- Generous time-off policies (vacation days, sick time, and personal days)
WORKING CONDITIONS:
This position works in the office and community. Sistering is a 24/7 operation, fast paced, intense environment. There may be the risk of exposure to potentially unpredictable behaviours and situations. Sistering is a pet friendly facility and as such, employees can expect to be in the proximity of animals.
Sistering is an Equal Opportunity Employer; we welcome and encourage applications from black, racialized persons/visible minorities, Indigenous persons, persons with disabilities, ethnic minorities, and persons of minority sexual orientations and gender identities. Those who require special accommodation through the interview process will be provided with the appropriate support.
This role is an open vacancy, and we encourage all qualified candidates to apply. Applicants will be informed of the outcome following an interview as per Ontario employment regulations.