Director, Employment Services

About The Career Foundation

The Career Foundation is a dynamic non-profit organization that offers a wide range of employment, training, and HR services to job seekers and employers. Since its inception in 1988, The Career Foundation has steadily expanded its services. Operating out of multiple locations, we now help thousands of people each year successfully accomplish their employment goals. Our team of dedicated professionals has described The Career Foundation as caring, compassionate, innovative, and team-oriented. For more information about us and our services, please visit our website at CareerFoundation.com.

Some of the benefits and features available to our employees include:

• Competitive compensation
• A comprehensive health benefits plan that includes massage therapy, naturopath services, travel coverage, and much more
• A comprehensive dental insurance plan
• An RRSP Matching benefit
• An Employee & Family Assistance program
• Employee wellness initiatives
• Paid days off for religious observance purposes
• Paid days off for personal wellness purposes

Position Type: Full-time (37.5 hours per week)

Experience Required: 5+ years

Number of Positions: 1

Reports To: COO

Position Summary

In this executive-level position, the Director, Employment Services provides strategic leadership and oversight for a designated portfolio of funded employment and training programs delivered by The Career Foundation. This position is responsible for ensuring the success, quality, and growth of all assigned programs through effective operational management, performance leadership, quality assurance, evaluation, reporting, and budget oversight.

The Director, Employment Services manages and collaborates closely with program management to ensure that program outcomes consistently meet or exceed established targets, while maintaining a client-centered approach that addresses the needs of diverse communities and ensures programs operate at a high level of effectiveness and efficiency.

In addition to internal leadership, the Director, Employment Services leads stakeholder relationship management by engaging with job seekers, community partners, employers, training providers, associations, networks, funders, and other key stakeholders. This engagement strengthens collaboration and expands opportunities for program participants and the organization.

Key areas of oversight for the Director, Employment Services include operational management, funder collaboration and negotiation, business planning and proposal development, project planning, financial management, target achievement, and comprehensive program evaluation. The role also involves initiating partnership initiatives, resolving conflicts, and building trust-based, long-term relationships that support program success.

The Director, Employment Services continually seeks opportunities to grow, enhance, and expand contracts and funding streams. The role also represents The Career Foundation at events, meetings, and strategic initiatives. As a member of the executive team, the Director, Employment Services holds signing authority and actively participates in senior-level planning and decision-making.

Base Location and Travel Requirements

The designated base location for this opportunity is our Head Office located in North York (Lawrence Ave. W. & Allen Rd.). The Director, Employment Services is also required to travel regularly to all program sites within the GTHA under the assigned portfolio of programs to provide effective oversight and fulfill the core deliverables of the position. The role also currently permits a hybrid-remote work schedule, allowing for one work-from-home day per week, based on operational requirements and performance. A full-time in-office work arrangement is also available, if preferred.

The successful candidate should possess a valid Ontario G driver’s licence and a vehicle for frequent travel between locations and other stakeholder sites across the GTHA.

Vulnerable Sector Check Requirement

An offer of employment for this opportunity will be contingent on the incumbent providing an acceptable Vulnerable Sector Check (VSC).

Responsibilities include:

Strategic Leadership and Portfolio Oversight

• Provides overall strategic direction and leadership for an assigned portfolio of employment and training programs across multiple locations in the GTHA.
• Ensures all assigned programs operate at a highly effective and efficient level, maintaining a client-centered approach that meets the needs of diverse communities.
• Stays abreast of environmental factors such as industry changes, government priorities, and labour market conditions, and evaluates and revises program models and systems when needed to ensure long-term success.
• Seeks opportunities to grow, enhance, and expand current funding contracts with additional funding and deliverables.
• Works with program managers and coordinators on quality proposal and business plan submission processes to ensure successful renewal of current contracts.
• Represents The Career Foundation at events, meetings, networking sessions, and initiatives as needed, including serving as either an attendee or speaker.
• Performs other relevant responsibilities as needed.

Program Development and Strategic Growth

• Leads the identification, development, and pursuit of new program opportunities aligned with The Career Foundation’s strategic goals and community needs.
• Oversees the preparation and delivery of high-quality proposals to public and private funders, ensuring responsiveness to requirements and competitiveness in the sector.
• Participates in annual business planning, including reviewing past outcomes and setting priorities for future growth initiatives.
• Stays abreast of funding prospects, labour market trends, and emerging client needs to proactively position The Career Foundation for new opportunities.
• Builds strategic linkages and partnerships with community organizations, employers, and training providers to co-create innovative service models.
• Collaborates with managers, coordinators, and the executive team to ensure readiness to respond to appropriate funding solicitations and opportunities.
• Performs other relevant responsibilities as needed.

Program Operations and Performance Management

• Leads program managers and coordinators under the assigned portfolio to ensure projects consistently meet targets and budget expectations.
• Streamlines processes and systems to ensure programs and sites operate in sync wherever possible.
• Maintains accessible tracking systems for managers, coordinators, and the executive team to monitor progress toward targets and expenditure goals.
• Reviews, approves, and signs assigned program reports, ensuring they are high-quality and submitted on time.
• Works with program managers and coordinators to negotiate contract terms with funders and requests amendments as needed.
• Reviews and signs contracts received from funders, ensuring thorough contract reviews are conducted and documented.
• Coordinates tasks related to special requests from funders, such as managing complex client cases.
• Performs other relevant responsibilities as needed.

People Leadership and Management Development

• Provides training and orientation to new managers and program coordinators to ensure they understand organizational expectations and systems.
• Provides regular coaching and professional development opportunities to develop the talent of management staff.
• Continuously monitors management performance, conducting ongoing reviews and appraisals to ensure managers meet and exceed role expectations.
• Supports program managers and coordinators with problem-solving as needed.
• Participates in the recruitment process and conducts interviews for managerial positions under assigned portfolio when needed.
• Reviews and approves vacation requests from program managers and coordinators under assigned portfolio to ensure appropriate coverage and continuity.
• Assumes executive-level responsibility for ensuring that staff at all levels under assigned portfolio consistently meet targets and role expectations.
• Supports program managers and coordinators in developing effective relationships with partners and negotiating or setting up sub-contracting agreements as needed.
• Reviews and signs community partner support letters, MOUs, and contracting partner agreements.
• Handles customer complaints that require escalation to a senior level, ensuring they are resolved professionally and in alignment with organizational policies and values.
• Performs other relevant responsibilities as needed.

Funder and Stakeholder Relations

• Serves as the primary point of contact for funder communications for programs under assigned portfolio, ensuring inquiries are answered in a timely and professional manner.
• Organizes and coordinates contract amendments with funders as needed.
• Prepares for and attends all funder audits with management staff, putting plans in place to ensure any recommendations for improvement are addressed and implemented.
• Works with management staff to make special requests to funders related to contracts, budgets, and program activities as needed.
• Develops and maintains strong relationships with employers, trainers, associations, networks, community partners, and other key stakeholders.
• Builds rapport and trust to establish long-lasting partnerships that support program success and community impact.
• Performs other relevant responsibilities as needed.

Financial Oversight and Contract Management

• Carefully manages and monitors all program budgets to ensure financial targets and funder expectations are consistently met.
• Approves and signs managerial expense reports and supplier invoices as needed.
• Works with the executive team and finance department to ensure accurate, timely budget reporting and compliance with contractual obligations.
• Works in collaboration with the finance department to ensure robust financial management practices are in place and adhered to across all assigned programs and sites.
• Collaborates with program managers and coordinators to negotiate contract terms with funders, ensuring sustainability and growth of services.
• Performs other relevant responsibilities as needed.

Evaluation, Quality Assurance, and Continuous Improvement

• Works in collaboration with the Director of Quality Assurance to ensure quality assurance monitoring systems are in place to evaluate compliance related to client service, file documentation, budget management practices, and other policies and procedures at the organization.
• Collaborates with the Director of Quality Assurance and the Manager of Digital Services and Strategies to ensure systems effectively support program operations and quality service delivery.
• Regularly evaluates program effectiveness, client outcomes, and operational efficiency to identify opportunities for continuous improvement.
• Leads change management initiatives to ensure successful adoption of new processes, systems, and strategies across all locations.
• Performs other relevant responsibilities as needed.

External Representation and Partnership Development

• Represents The Career Foundation at community and employer advisory meetings, funder meetings, and other external partner events.
• Builds and maintains strong relationships with employers, community partners, training providers, associations, and networks.
• Promotes the organization’s mission, values, and services in the community to enhance visibility and reputation.
• Supports management staff in developing partnership initiatives and negotiating roles, responsibilities, and agreements with external partners.
• Actively seeks opportunities to establish new partnerships and projects that advance organizational goals and improve client outcomes.
• Performs other relevant responsibilities as needed.

Qualifications/ Skills Required:

• Post-secondary degree in business management, human services, or a related field relevant to the scope of the position.
• Minimum of 5 years’ progressive leadership experience overseeing large teams in the employment services or recruitment sectors, with a proven ability to strategically manage program operations and lead teams to successful outcomes
• Budget and financial analysis expertise is required.
• Experience preparing proposals that generate funding, liaising with funders and other stakeholders, and demonstrating strong negotiation skills.
• Excellent organization, analytical, time management and administrative skills.
• Exceptional rapport-building and relationship development skills.
• Strong problem-solving and conflict resolution skills, with the ability to mediate issues and implement effective solutions.
• Excellent verbal and written English communication skills, with experience writing high-quality reports. Bilingualism is considered an asset.
• Tech-savvy, with experience using CRM systems, advanced Excel functions, and Power BI, considered a strong asset.
• Advanced proficiency in Microsoft Office Suite, including Outlook 365 applications. Must possess the aptitude and willingness to learn and work with new online systems and technologies.
• Excellent interpersonal skills, with a proven ability to demonstrate tact, diplomacy, and exceptional customer service.
• Professional and courteous approach to client service, with a high level of respect for the diversity of the people served.
• High ethics with a proven ability to maintain sensitive information, uphold confidentiality standards, and exhibit sound judgment.
• Capable of working under pressure and meeting deadlines in a fast-paced environment with resilience.
• Ontario G-class driver’s licence and reliable access to a vehicle for frequent travel to program sites and other stakeholder locations across the GTHA.
• Willingness and flexibility to occasionally work outside regular business hours as needed.
• Proactive and solutions-oriented leader who fosters a positive team culture, leads by example, and consistently demonstrates initiative, accountability, and a strong commitment to collaboration and shared success.

The Career Foundation’s Commitment:

The Career Foundation is committed to diversity and inclusion and aims to create a healthy and rewarding environment for all. We welcome applications from qualified individuals who represent the diversity of the people we proudly serve, including, but not limited to, visible minorities, women, persons with disabilities, Indigenous peoples, and individuals of all genders and sexual orientation. The Career Foundation, in accordance with the Accessibility for Ontarians with Disabilities Act (AODA), is also committed to accommodating applicants with disabilities throughout the recruitment process. We will work with candidates requesting accommodation at any stage of the hiring process.