Program Supervisor

StepStones For Youth; Toronto; On-site; CAD 60,000 - 80,000; Full time

Job summary

StepStones for Youth is looking for a dedicated Supervisor to lead the Building Connections Program. This program aims to empower youth from the child welfare system through supportive relationships and community engagement, fostering resilience and stability. The role involves mentoring staff, overseeing program activities, and ensuring effective service delivery, making a meaningful impact in the lives of vulnerable youth.

Benefits

Comprehensive Benefit Package

Flexible vacation policy

Professional development allowance

Qualifications

• 7–10 years of leadership experience in social services.
• Experience supporting youth involved in child welfare.
• Demonstrated expertise in case management and service delivery.

Responsibilities

• Mentoring and supporting youth service staff.
• Overseeing engagement activities and major events.
• Managing the recruitment and training of volunteers.

Skills

Leadership

Communication

Problem-Solving

Case Management

Community Engagement

Education

Degree in Social Sciences or Social Work

Tools

Microsoft Office

Case Management Platforms

Job description

The Organization

We value and celebrate diversity:We are committed to a selection process and work environment that is inclusive and barrier free. We encourage applications from all backgrounds and communities and are committed to having a team made up of people with diverse skills, experiences, and abilities. We actively encourage BIPOC and LGBTQ+ applicants to apply and we value the positive impact that diversity has on our teams. We are committed to equity, diversity, and social inclusion within our workforce and in all opportunities provided at StepStones. Accommodations will be provided in accordance with the Ontario Human Rights Code.

StepStones for Youth (www.stepstonesforyouth.com) is an innovative and dynamic charitable organization in Toronto dedicated to providing intervention and sustainable support for children and youth. Many of these youth are exiting the foster care and group home system or are currently living in foster homes and shelters.

Our goal is to create positive and meaningful connections; increase school engagement, high school graduation, and post-secondary enrolment; and increase stable housing, improved mental and physical health, and strong support networks. StepStones adheres to a “whatever it takes” approach to servicing youth and we go above and beyond to support their needs.

Why Work With Us:

• 
  Comprehensive Benefit Package: includes 3K to paramedical services, and Short Term and Long-Term Disability including Employee Assistance Program (EAP) & Grief counselling available free of charge (in addition to benefits) for work related incidents
• 
  Time-Off: 17 days vacation with a 1-day vacation increase per year worked, up to 35 day’s vacation
• 
  Leave:8sick days, 3 personal days, 1.5 medical appointment days, bereavement allowance
• 
  Professional Development:Training allowance of $700 per year
• 
  Reimbursements:Mileageprovided at a competitive rateand all staff are given a petty cash budget
• 
  Tools you need to succeed: All staff receive a MacBook, Headphonesand access to our mobile friendly CRM system
• 
  Extended Break: 1.5 lunch break healthy living program when you exercise for 30 minutes during lunch

The Opportunity

StepStones for Youth is seeking a Supervisor to support our Building Connections Program. This program is rooted in the belief that meaningful, supportive relationships provide youth from the child welfare system, with the stability and resilience needed to reduce the likelihood of negative long-term outcomes. We focus on shifting primary support responsibilities from professional service providers to trusted, non-professional figures in the youth’s life—strengthening their natural support networks. Through targeted training and consistent support, we empower communities and caregivers to take on these roles.

This is a unique opportunity to make a lasting difference in the lives of some of society’s most vulnerable youth.

Position Overview

Reporting to the Programs Director, the Program Supervisor plays a key leadership role by mentoring and supporting youth service staff in their day-to-day efforts. The ideal candidate brings strong clinical insight and assessment skills to guide frontline work and ensure excellence in service delivery. The Program Supervisor will also cultivate relationships with external partners and stay current on relevant community resources to ensure responsive, wrap-around care for youth.

Key Responsibilities

Engagement Coordination

• Lead the planning and delivery of engagement activities, including:
  • Annual engagement calendar
  • Weekly Tuesday dinners and monthly Saturday events (excluding major holidays)
• Oversee major events, such as:
  • June BBQ
  • October Harvest Dinner
  • December Holiday Celebration
  • February Family Night
• Manage four annual workshop series, examples include photography, cooking, basket weaving, and yoga.

Supervision of Connection Coordinators

• Provide regular one-on-one and group supervision for Connections Coordinators.
• Review case notes, provide strategic guidance, and assist with developing action plans to support positive outcomes for youth.
• Ensure adherence to ethical, legal, and organizational standards, including proper documentation and compliance with regulations.
• Identify professional development needs and coordinate training in collaboration with the Programs Director.
• Support the facilitation of internal training sessions, workshops, and continuing education.

Volunteer Program Oversight

• Lead the implementation and expansion of the volunteer program.
• Supervise the recruitment, training, and matching of mentors with youth and frontline staff.
• Manage the corporate volunteer program, especially during high-demand seasons like the holidays.
• Ensure all mentors are appropriately vetted and records maintained through DonorPerfect.

Additional Responsibilities

• Manage distribution of TTC transit tickets.
• Provide supervision and support to staff delivering direct services, including:
  • Weekly check-ins
  • Goal setting
  • Training and development
    
  • Performance evaluations
  • Approving expense reimbursements
• Participate in organizational events and represent StepStones at community engagements.
• Attend weekly leadership and engagement meetings.
• Undertake special projects and other duties aligned with organizational priorities.

Other duties as assigned

Qualifications and Requirements

• Degree in Social Sciences, Social Work, or a related field.
• 7–10 years of leadership experience in social services, ideally with experience supporting youth involved in the child welfare system.
• Demonstrated expertise in case management, supervision, and service delivery.
• In-depth knowledge of child protection services, foster care, adolescent development, and community engagement strategies for marginalized youth.
• Proficiency with digital tools, including Microsoft Office and case management platforms.
• Strong communication skills—written and verbal—with proven leadership, decision-making, and problem-solving abilities.
• Ability to manage competing priorities and maintain professionalism in a fast-paced, multi-stakeholder environment.
• High degree of discretion, diplomacy, and tact in handling confidential matters.
• Valid Ontario G Class Driver’s License.

Equal opportunity

StepStones values the unique skills and experiences each individual has to offer and we are committed to creating an inclusive and accessible organization. We are committed to providing barrier-free and accessible employment practices in compliance with the Accessibility for Ontarians with Disabilities Act (AODA). If you require accommodation to participate fully in our recruitment processes, please let us know when we contact you.

StepStones is an equal opportunity employer seeking to live its values in all we do. We are committed to taking proactive steps to provide and create opportunities for historically marginalized groups. We seek applicants who will strengthen our commitment to diversity, equality, and inclusion. We strongly encourage qualified candidates from Indigenous, Black, and other racialized persons, 2SLGBTQI+ people, individuals with disabilities, and other members of marginalized communities to consider working with and for StepStones. We recognize that structural barriers shape experiences and job qualifications, and therefore we seek to use employment equity to evaluate candidates who meet the required qualifications.

We thank all applicants for their interest in this position; however, only those applicants will be selected for an interview will be contacted. No phone calls or in person submissions please.