JOB DESCRIPTION
POSITION TITLE: Supervisor, Programs & Services
PROGRAM: AI Upskilling - Program Operations
COMPANY: Skills for Change
LOCATION: 65 Overlea Blvd, 2nd Floor Suite 260, Toronto, ON M4H 1P1
SALARY $65,000-$68,000
REPORTS TO: Manager – AI Upskilling & Workforce Development
CONTRACT TYPE: Full-time (indefinite)
HOURS: 35 hours per week (Monday-Friday, Hybrid)
GENERAL ACCOUNTABILITY:
With over 40 years of operations, Skills for Change is a highly respected charity with a province-wide reputation for pioneering programs that respond to shifting immigration and workplace trends and lead to employment. We offer a range of accelerated programs including mentoring, employment, mental health, entrepreneurship, settlement, language training, and specialized programs for trades, women, Black communities, seniors, and youth.
Skills for Change recognizes the urgent need to provide AI skill development programs to address the challenges faced by racialized and newcomer youth, women, and other marginalized communities who experience high unemployment and underemployment despite constituting a significant portion of Canada's growing population.
PROGRAM NATURE & SCOPE:
The AI Upskilling Program aims to reach as many Canadians, newcomers, refugees & other equity-seeking groups in gaining foundational AI literacy. The Supervisor, AI Upskilling will be accountable for the operations and continuous improvement of the AI Upskilling Program. Reporting directly to the Manager, AI Upskilling, the Supervisor manages frontline staff and has the primary responsibility of ensuring operational excellence.
THE IDEAL CANDIDATE HAS:
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Past experience in managing the operations of educational or workforce programs
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A strong sense of project management and ability to run multi‑stage, multi‑stakeholder initiatives.
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A strong affinity for using technology, automation, and data to drive continuous improvement in program delivery.
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Demonstrated understanding of barriers faced by equity‑deserving and newcomer communities.
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Ability to lead a team, coach staff, and maintain a positive, collaborative work environment.
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Highly skilled in Excel, SharePoint, Power Automate, workflow systems, and reporting dashboards.
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Excellent communication, facilitation, documentation, and stakeholder engagement skills.
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Day-to-day- Program Operations
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Oversee the daily operations of the AI Upskilling Program, ensuring seamless learner experience across onboarding, training, support, and program completion.
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Ensure Client Service Navigators and trainers utilize systems, workflows, and guidelines to their full potential.
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Monitor program outcomes and KPIs (completion rates, engagement levels, learner feedback, automation errors, etc.).
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Create feedback loops by reviewing survey data, session analytics, and team reports
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Troubleshoot challenges proactively, providing frontline support to staff when complex learner or technology issues arise.
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Ensure program delivery aligns with funder agreements, reporting requirements, and Skills for Change standards.
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Coordinate across locations and departments to ensure consistency in delivery.
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Operational Excellence & Systems Management
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Support, refine, and implement operational processes to increase efficiency and quality.
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Support the adoption and integration of automation workflows in Power Automate, optimizing repetitive processes (e.g., onboarding emails, attendance tracking, survey workflows).
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Oversee SharePoint structures, permissions, and document management to ensure data accuracy and accessibility.
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Maintain Excel reporting tools and dashboards to track participant metrics, staff performance indicators, and program milestones.
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Monitor staff data entry practices to ensure data integrity and compliance.
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Identify operational risks and implement mitigation strategies, escalating where appropriate.
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Training Coordination
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Coordinate schedules, trainers, guest speakers (when applicable), and session logistics.
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Track learner progress data and create weekly reports to discuss with the Manager
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Stakeholder Engagement & Cross‑Departmental Collaboration
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Liaise with Employer Engagement, Marketing, Research, and other departments to align program goals with organizational strategy.
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Participate in cross‑departmental working groups, sharing insights and operational considerations.
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Build external partnerships that enhance learner experience.
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Represent the AI Upskilling Program at events, community networks, and external committees.
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Administration, Reporting & Budget Management
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Support the preparation monthly, quarterly, and annual reports for internal leadership and funders.
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Monitor program targets, taking corrective action when indicators fall behind.
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Support with the management of program budgets, approve expenses, oversee purchasing, and maintain financial documentation.
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Track statistical data (enrolment, demographics, completion rates, employment outcomes) and ensure timely submission.
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Use data insights to identify and address inequities in program participation or outcomes.
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Attend management meetings, staff meetings, and cross-site coordination sessions.
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Ensure compliance with funder guidelines and Skills for Change policies.
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Team Leadership:
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Coach, support, and manage a team of Client Support Navigators to coordinate and deliver upskilling training and coaching, ensuring staff feel confident, resourced, and aligned with program goals.
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Continually work at building and maintaining a strong team environment, fostering collaboration, psychological safety, and a culture of continuous learning.
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Oversee hiring, onboarding, probation evaluation, and ongoing performance management of staff.
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Share professional development opportunities, updates on AI tools, and emerging digital learning practices to ensure the team stays current with sector trends.
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Facilitate clear communication channels, ensuring staff understand expectations, priorities, workflows, and program changes.
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Support staff in problem‑solving around challenging client cases, onboarding issues, learner engagement barriers, or technology disruptions.
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Ensure staff uphold anti‑racist, anti‑oppressive, equity‑informed service delivery principles consistent with Skills for Change values.
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Encourage team collaboration across departments, supporting integrated service delivery between AI Upskilling, Employment Services, BCAP, Sustainable Communities, etc.
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Project Management:
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Maintain project plans covering timelines, workflows, reporting cycles, and training schedules.
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Monitor project milestones, KPIs, and risks, taking corrective action when targets fall behind.
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Coordinate cross‑departmental contributions to ensure smooth, aligned program delivery.
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Ensure high data integrity through consistent tracking, documentation, and quality assurance processes.
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Handle additional tasks as required by Program Manager or Program Director
SKILLS, EDUCATION AND ATTRIBUTES:
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Education: Post‑secondary degree (ideally in education, social work, career development, project management, or a related field).
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Experience:
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Minimum three years in educational program operations or workforce development.
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Minimum two years supervising staff within a unionized environment
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Experience working with underserved communities and/or blended learning environments are preferred
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Workforce Development: Demonstrated experience supporting racialized and underserved communities in developing career-ready skills.
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Technical Knowledge:
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Advanced Excel (dashboards, formulas, data validation).
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Strong proficiency with SharePoint and Power Automate.
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Familiarity with AI tools such as Gemini, ChatGPT, Claude, Perplexity, Notion, etc. are preferred
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Project Management: Experience managing projects from start to finish. Project Management education is an asset.
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Data & Reporting: Experience collecting, analyzing and reporting data
Should be comfortable with Excel, SharePoint, Power Automate & PowerBI -
Attributes
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Analytical, detail‑oriented, and solutions‑driven.
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Strong communication, facilitation, and interpersonal skills.
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Organized, adaptable, and comfortable managing multiple priorities.
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Equity Focus: A strong understanding of the barriers faced by equity-deserving communities and innovative ways to address them.
ADDITIONAL INFO: How to apply
To apply, please submit your resume and cover letter, detailing your two most significant professional achievements related to educational program operations management, customer success, and/or AI upskilling. Applications will be reviewed on a rolling basis, and early submissions are encouraged.
As part of our commitment to diversity & inclusion, racial justice, and reconciliation, Skills for Change encourages applications from those who identify as Black, Indigenous, 2SLGBTQ+, racialized, and other under-represented communities. Skills for Change offers accommodation for applicants with disabilities in each stage of the hiring process. If you are contacted regarding a job opportunity, please advise if you require accommodation. This document is available in an alternate format on request. We thank all applicants for their interest in this position however only those selected for an interview will be contacted.
