Supervisor Programs

Supervisor, Programs & Operations

Terms of Employment:
 six-month contract -Full-time (37.5 hours per week)

Salary:
 50,000- 60,000

Location:
 Oakville

Reports to:
 CEO

Role Summary

The 
Supervisor, Programs & Operations
 is a hybrid leadership role that integrates program delivery, operational oversight, and strategic growth. This position combines hands-on program management and supervision with organizational leadership responsibilities, ensuring excellence in employment and mentorship services while strengthening internal systems, partnerships, and revenue sustainability.

This role is ideal for a dynamic leader who can balance frontline impact with big-picture thinking—supporting participants directly, leading staff, ensuring compliance and performance, and contributing to fundraising, brand growth, and long-term organizational sustainability.

Key ResponsibilitiesProgram Delivery & Client Services

·      Maintain a caseload of participants, providing career counselling, employment planning, job search support, and barrier resolution.

·      Conduct and approve milestone verification at 1-, 3-, 6-, and 12-month intervals using employment letters, pay stubs, or Employment Status Attestations.

·      Approve financial supports for participants and employers in alignment with program and funder guidelines.

·      Ensure accurate and timely documentation of services, outreach, and outcomes in FedcapCARES (FCC) or other designated systems.

Team Leadership & Program Oversight

·      Provide day-to-day leadership, coaching, and supervision to program staff.

·      Review and approve milestone and financial submissions prior to submission to the Service System Manager (SSM).

·      Monitor performance against KPIs, funding agreements, and contractual deliverables.

·      Prepare and submit quarterly activity and performance reports, analyzing trends and recommending improvements.

·      Participate in regular performance review and accountability meetings with the SSM and funders.

·      Support recruitment, onboarding, training, and performance management of staff.

Operations, Compliance & Financial Stewardship

·      Strengthen internal systems, processes, and workflows to support efficiency and scalability.

·      Ensure compliance with all program, financial, privacy, accessibility, and equity standards.

·      Oversee data integrity, reporting accuracy, and audit readiness.

·      Contribute to sound financial management by ensuring appropriate allocation, approval, and tracking of participant and employer supports.

Fundraising, Partnerships & Brand Growth

·      Support fundraising initiatives, including corporate sponsorships, grants, and donor stewardship.

·      Collaborate with leadership to grow and manage a donor pipeline and support a monthly donor program.

·      Strengthen partnerships with corporations, government, schools, and community organizations.

·      Contribute to storytelling, reporting, and impact communications that elevate BMI's brand and visibility.

Strategic Leadership

·      Contribute to organizational planning, board reporting, and strategic decision-making.

·      Support revenue diversification and long-term sustainability initiatives.

·      Identify opportunities for program expansion, innovation, and increased community impact.

Education, Experience & Attributes

Education
 - Post-secondary education in human services, social work, nonprofit management, career development, or a related field. - Career Development Practitioner (CDP) certification or equivalent is an asset. - Knowledge of financial management, reporting, or nonprofit accounting is an asset.

Experience
 - Minimum 3 years' experience in employment services, mentorship, or community-based programming. - At least 2 years' experience in a leadership, supervisory, or management role. - Demonstrated experience supporting individuals facing complex barriers to employment. - Experience with outcome-based funding models, performance monitoring, and compliance reporting. - Exposure to fundraising, donor relations, or partnership development is a strong asset.

Attributes
 - Strong people leadership skills with the ability to balance hands-on service delivery and strategic oversight. - Highly organized with strong analytical, problem-solving, and decision-making abilities. - Exceptional professionalism, discretion, and judgment. - Strong written and verbal communication skills, including reporting and stakeholder engagement. - Detail-oriented with a strong commitment to accountability, equity, and excellence.

Skills & Requirements

·      Strong understanding of employment services, labour market trends, and community resources.

·      Familiarity with outcome-based funding and milestone reporting.

·      Proficiency in MS Office and client management systems (e.g., FedcapCARES).

·      Ability to travel locally within the catchment area (valid driver's licence required).

·      Clear criminal record check.

About Black Mentorship Inc.

Black Mentorship Inc. (BMI) is a federally registered Canadian charity dedicated to empowering Black youth and professionals through mentorship, employment pathways, leadership development, and strategic partnerships.

How to Apply

Please submit your resume and cover letter to