Supervisor, Programs & Services

Skills For Change Metro•Toronto, ON

11h•Hybrid

About The Position

Skills for Change is a respected charity with over 40 years of experience in providing employment and training programs. They are launching an AI Upskilling Program to address the need for AI skill development among racialized and newcomer youth, women, and other marginalized communities who face high unemployment and underemployment. The Supervisor, AI Upskilling will be responsible for the operations and continuous improvement of this program, managing frontline staff and ensuring operational excellence.

Requirements

Minimum three years in educational program operations or workforce development.
Minimum two years supervising staff within a unionized environment.
Advanced Excel (dashboards, formulas, data validation).
Strong proficiency with SharePoint and Power Automate.
Experience managing projects from start to finish.
Experience collecting, analyzing and reporting data.
Comfortable with Excel, SharePoint, Power Automate & PowerBI.
Analytical, detail-oriented, and solutions-driven.
Strong communication, facilitation, and interpersonal skills.
Organized, adaptable, and comfortable managing multiple priorities.
A strong understanding of the barriers faced by equity-deserving communities and innovative ways to address them.

Nice To Haves

Experience working with underserved communities and/or blended learning environments are preferred.
Familiarity with AI tools such as Gemini, ChatGPT, Claude, Perplexity, Notion, etc. are preferred.
Project Management education is an asset.

Responsibilities

Oversee the daily operations of the AI Upskilling Program, ensuring seamless learner experience across onboarding, training, support, and program completion.
Ensure Client Service Navigators and trainers utilize systems, workflows, and guidelines to their full potential.
Monitor program outcomes and KPIs (completion rates, engagement levels, learner feedback, automation errors, etc.).
Create feedback loops by reviewing survey data, session analytics, and team reports.
Troubleshoot challenges proactively, providing frontline support to staff when complex learner or technology issues arise.
Ensure program delivery aligns with funder agreements, reporting requirements, and Skills for Change standards.
Coordinate across locations and departments to ensure consistency in delivery.
Support, refine, and implement operational processes to increase efficiency and quality.
Support the adoption and integration of automation workflows in Power Automate, optimizing repetitive processes (e.g., onboarding emails, attendance tracking, survey workflows).
Oversee SharePoint structures, permissions, and document management to ensure data accuracy and accessibility.
Maintain Excel reporting tools and dashboards to track participant metrics, staff performance indicators, and program milestones.
Monitor staff data entry practices to ensure data integrity and compliance.
Identify operational risks and implement mitigation strategies, escalating where appropriate.
Coordinate schedules, trainers, guest speakers (when applicable), and session logistics.
Track learner progress data and create weekly reports to discuss with the Manager.
Liaise with Employer Engagement, Marketing, Research, and other departments to align program goals with organizational strategy.
Participate in cross-departmental working groups, sharing insights and operational considerations.
Build external partnerships that enhance learner experience.
Represent the AI Upskilling Program at events, community networks, and external committees.
Support the preparation of monthly, quarterly, and annual reports for internal leadership and funders.
Monitor program targets, taking corrective action when indicators fall behind.
Support with the management of program budgets, approve expenses, oversee purchasing, and maintain financial documentation.
Track statistical data (enrolment, demographics, completion rates, employment outcomes) and ensure timely submission.
Use data insights to identify and address inequities in program participation or outcomes.
Attend management meetings, staff meetings, and cross-site coordination sessions.
Ensure compliance with funder guidelines and Skills for Change policies.
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.
Continually work at building and maintaining a strong team environment, fostering collaboration, psychological safety, and a culture of continuous learning.
Oversee hiring, onboarding, probation evaluation, and ongoing performance management of staff.
Share professional development opportunities, updates on AI tools, and emerging digital learning practices to ensure the team stays current with sector trends.
Facilitate clear communication channels, ensuring staff understand expectations, priorities, workflows, and program changes.
Support staff in problem-solving around challenging client cases, onboarding issues, learner engagement barriers, or technology disruptions.
Ensure staff uphold anti-racist, anti-oppressive, equity-informed service delivery principles consistent with Skills for Change values.
Encourage team collaboration across departments, supporting integrated service delivery between AI Upskilling, Employment Services, BCAP, Sustainable Communities, etc.
Maintain project plans covering timelines, workflows, reporting cycles, and training schedules.
Monitor project milestones, KPIs, and risks, taking corrective action when targets fall behind.
Coordinate cross-departmental contributions to ensure smooth, aligned program delivery.
Ensure high data integrity through consistent tracking, documentation, and quality assurance processes.
Handle additional tasks as required by Program Manager or Program Director