Regional Manager – Winnipeg Region

Workplace Education Manitoba is looking for a Regional Manager – Winnipeg Region who will report to the Executive Director of Operations and be responsible for leading and managing MEET’s Skills for Success activities and service delivery within the Winnipeg region.

This position provides operational, project and people leadership to ensure effective, high-quality service delivery that aligns with MEET’s mission, funding agreements and approved regional objectives. The Regional Manager develops and maintains regional partnerships, oversees projects, resources and service providers, and provides direction, guidance and support to regional employees. Operating with a high degree of autonomy, the Regional Manager acts in the best interests of the organization and upholds MEET’s core values of leadership, collaboration, customer service and innovation.

Key Responsibilities

Regional Operations & Program Leadership

• Lead and manage Skills for Success service delivery within the Winnipeg region, ensuring alignment with MEET’s mission, strategic objectives and funding agreements.
• Coordinate and oversee regional activities, including Workplace, Apprenticeship, WEM Centre and pre-employment programming, as applicable.
• Participate in strategic and operational planning and lead the implementation of approved regional initiatives.
• Identify regional Skills for Success needs, priorities and opportunities and work with partners and internal teams to develop appropriate responses.
• Monitor and evaluate program and service delivery to ensure quality, efficiency, effectiveness and achievement of intended outcomes.
• Ensure appropriate allocation of staff, service providers and other resources to support successful service delivery.
• Stay informed on workforce development, training innovation and labour market needs relevant to the region.
• Serve as a positive, knowledgeable and professional representative of MEET in all interactions with staff, partners, funders, government representatives and other stakeholders.

Partnership Development & Regional Engagement

• Initiate, develop and maintain effective partnerships with workplaces, non-profits, Indigenous Nations and communities, government representatives, and other regional stakeholders.
• Build awareness of Skills for Success through presentations, meetings, consultations and ongoing relationship development.
• Conduct or coordinate needs assessments with partners to identify Skills for Success opportunities and priorities.
• Represent MEET professionally and contribute to the development of regional partnerships and future activities.

Project Development & Management

• Identify, develop and coordinate approved Skills for Success projects within the region.
• Develop project plans in collaboration with partners and internal teams, including learning objectives, activities, timelines, partnerships, resources and evaluation strategies.
• Support the development of customized Skills for Success training and assessment responses based on identified needs, past successes and available or newly developed content.
• Manage project activities, deliverables and timelines from initiation through completion.
• Select, engage and coordinate appropriate service providers and ensure services meet project requirements and quality standards.
• Monitor project progression and provide ongoing project support, communication and problem-solving as required.
• Track project expenditures, budgets, invoices and financial commitments to ensure activities remain within approved budgets.
• Complete or coordinate project evaluations, reporting and documentation required by MEET and funders.
• Identify project risks, emerging issues or changes in scope and address or escalate them as appropriate.

People Leadership & Team Development

• Provide direct leadership, supervision and day-to-day management to employees assigned to the region.
• Foster a positive, respectful, inclusive and collaborative work environment that promotes teamwork, accountability, innovation and open communication.
• Establish clear individual and team goals, priorities, expectations and deliverables and monitor progress toward their completion.
• Provide direction, coaching, feedback and mentorship to support effective performance and professional growth.
• Monitor workload, scheduling, priorities and resource allocation to support balanced workloads, productivity and timely service delivery.
• Identify staff development and training needs and coordinate appropriate opportunities for skill-building and professional development.
• Support recruitment, selection and onboarding of regional employees in collaboration with HR.
• Address day-to-day performance, conduct, attendance and workplace concerns and work with HR on performance management, employee relations and other employment matters as required.
• Ensure employees understand and follow MEET policies, procedures, project requirements and applicable workplace practices.
• Serve as a liaison between regional employees and the broader leadership team.

Service Provider Management

• Recruit, select, engage and maintain effective working relationships with service providers, as appropriate.
• Provide direction and support to service providers to ensure project requirements, timelines and quality expectations are met.
• Monitor service-provider performance and deliverables and address issues as required.
• Ensure service-provider contracts and activities comply with approved project requirements and organizational standards.
• Support service-provider development activities and share relevant information, resources and best practices.

Management, Administration & Financial Accountability

• Direct and manage regional service delivery operations, including resource allocation, operational planning, partner relations, reporting and quality assurance.
• Manage and monitor regional budgets, expenditures, invoices, contracts and financial commitments within delegated authority.
• Maintain accurate project, financial, employee and administrative records and ensure required documentation and reporting are completed.
• Evaluate and improve regional administrative systems, processes and practices to enhance efficiency and effectiveness.
• Work collaboratively with HR on recruitment, onboarding, training, workplace safety, performance management, employee relations, compensation and compliance matters.
• Work with communications staff to support regional marketing, promotional initiatives, presentations and digital materials as appropriate.
• Provide regular updates to the Executive Director of Operations regarding regional activities, project performance, staffing, financial status, risks and emerging issues.
• Perform additional duties as assigned.

Qualifications & Requirements

• Experience in project management and coordination.
• Experience providing leadership and direct supervision to employees and/or teams.
• Ability to build and maintain partnerships with individuals, workplaces and organizations.
• Understanding of adult learning principles and experience working with adult learners.
• Understanding of Skills for Success responses, including assessment and training, and their implementation.
• Demonstrated organizational, coordination and time-management skills.
• Strong leadership skills, including the ability to identify change, support innovation and make sound decisions.
• Ability to manage multiple projects, priorities and changing regional needs.
• Excellent verbal, written, communication, negotiation and interpersonal skills.
• Effective and independent work skills, with the ability to collaborate across teams and functions.
• Experience with budget planning, expenditure tracking, financial management and reporting.
• Competence in recruitment, onboarding, staff development and performance management.
• Strong analytical and problem-solving skills.
• Advanced proficiency in Microsoft Office Suite (Outlook, Excel, PowerPoint, Word).
• High level of professionalism, integrity and discretion in handling confidential information.
• Flexible, collaborative and solution-focused approach to leadership.
• Ability to travel throughout the Winnipeg Region to oversee regional operations, WEM Centre activities, partnerships and training activities.
• Job Type: Full Time (37.5 hrs per week)
• Applicants must be legally entitled to work in Canada.
• The position involves periodic travel to oversee project activities and foster partnership development. Applicants must have access to a reliable personal vehicle.
• Successful applicant will be required to provide the results of the below listed safety checks.

Vulnerable Persons Check

Driver’s Abstract Check

If you are interested in joining a dynamic Organization, please submit your cover letter, resume and a list of references to Workplace Education Manitoba by Oct 28, 2026. Your application should clearly demonstrate how you meet the qualifications for the position.

To know more about WEM please visit Workplace Education Manitoba | Adult Training

Applicants may request reasonable accommodation related to the materials or activities used throughout the selection process.

This position will remain open until filled.

We thank all who apply and advise that only those selected for further consideration will be contacted.