Job Posting 85763

Director of Workforce Development
The Career Foundation
Toronto Metro area, Southern Ontario
Based in Toronto, Ontario
closes in 28 days (Fri, 9 Sep)
full time

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 seven locations, we now help thousands of people each year successfully accomplish their employment goals. Our team of dedicated professionals have described The Career Foundation as caring, compassionate, innovative, and team-oriented. For more information about us and our services, please visit our website at

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 Employee & Family Assistance program
  • An RRSP Matching plan
  • A Wellness program

Position Description: The Director of Workforce Development is responsible for developing and overseeing a growing suite of workforce development training programs at The Career Foundation to ensure project successes and positive outcomes. The Director  works closely with Managers and Program Coordinators of assigned programs to ensure that all targets are continuously met and exceeded through effective performance management, accurate and timely quality monitoring, evaluation, and reporting of all program activities, results, and budget management.

The Director of Workforce Development is responsible for ensuring that programs and services operate at a highly effective and efficient level, while maintaining a client-centered approach that meets the needs of a diverse community. The Director also oversees and drives stakeholder relationship management with trainers and employers, including Advisory Partners, Independent Contractors, and Training Providers (e.g., Private Career Colleges, Public Colleges, Trades Associations, Employer Consortiums, Unions, etc.).

Program oversight for which the Director of Workforce Development is responsible includes proposal submissions, project plans, budgets, targets, and program evaluation. Stakeholder engagement and management includes creating partnership initiatives and projects, negotiating roles and responsibilities, mediating, resolving conflicts, and developing rapport that creates trust and cordial working relationships, while establishing long lasting partnerships. The Director of Workforce Development continually seeks opportunities to grow, enhance, and expand current contracts, and represents The Career Foundation at events, meetings, and initiatives. As a member of the Executive team, the Director of Workforce Development has signing authority and takes part in senior-level planning meetings. 


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

Experience Required: 7+ years

Number of Positions: 1

Reports To: Chief Operating Officer

Base Location: This opportunity is available as a hybrid-remote position comprised of work-from-home functions and on-site work, with the option to work fully from the office, if preferred. The Director of Workforce Development develops and provides oversight for programs across Southern Ontario, both virtually and in-person. Official base location is The Career Foundation’s Head Office at Lawrence and Allen Rd. in Toronto, and travel will be required occasionally to other sites.

Start Date: Immediately

COVID-19 Vaccination Requirement: The Career Foundation is committed to the health and safety of its workforce. As of December 16, 2021, successful candidates for our internal employment opportunities must be fully vaccinated against COVID-19 and submit proof of same prior to receiving an official employment offer. Accommodations will be made where possible for qualifying medical or religious exemptions.


Position-Specific Responsibilities and Deliverables:


Staff Management (Program Managers/Coordinators, Partners, Independent Contractors, and Training Providers):

  • Provides training and orientation to new Program Managers/Coordinators.
  • Manages a team of Program Managers/Coordinators, Independent Contractors, Partners, and Training Providers, to ensure policies and procedures are adhered to and target numbers are accomplished.
  • Supports designated Program Managers/Coordinators with problem-solving and HR issues within their programs, including decision-making related to the employee selection process, and works in consultation with the Director of HR and Operations to solve HR matters that require escalation.
  • Works with Director of HR and Operations to create contracts and MOUs with independent contractors, partners, and training providers.
  • Handles performance concerns with staff, partners, independent contractors, and training providers.
  • Handles occasional customer complaints that escalate.
  • Reviews and approves Program Manager/Coordinator vacation requests.
  • Provides regular coaching to develop the talent of Program Managers/Coordinators.
  • Continuously monitors performance and conducts reviews/appraisals throughout the year to ensure that Program Managers/Coordinators are meeting and exceeding expectations.
  • Assumes full responsibility for ensuring that all designated Managers and Program Coordinators are meeting targets and role expectations.
  • Leads staff training and staff meetings and participates in case conferences as needed.
  • Documents performance issues and terminates agreements with staff, partners, independent contractors, and training providers as appropriate when remedies have been unsuccessful.
  • Cultivates a positive and collaborative working environment.

Project Oversight /Management:

  • Creates project work plans and timelines to ensure projects are running per the schedule and oversees all project components, including development and design, recruitment and intake, curriculum development, pre-employment workshops, sector-specific technical training, job matching and placement, and retention.
  • Oversees the development and monitoring of project work plans using Microsoft Suite project tools, including SharePoint, Forms, Planner, etc.
  • Resolves unforeseen challenges and obstacles and mediates between staff, partners, and funders to remedy the situations.
  • Works with Program Managers/Coordinators to establish participant learning outcomes with project partners and oversee curriculum development.
  • Oversees the creation of project forms, processes, and policies in cooperation with The Career Foundation’s project partners and Program Advisory Committees.
  • Ensures all projects meet targets, project deliverables, and budget management expectations.
  • Stays abreast of sector-specific environmental factors, such as upcoming industry changes, government priorities, and labour market conditions and evaluates and revises program models and systems to ensure long-term success.
  • Attends sector-specific industry events to build networks and industry knowledge.
  • Ensures that specialized projects have adequate insurance for unique activities, events, and initiatives.

Proposal Development:

  • Leads proposal submissions to ensure current contracts are renewed successfully.
  • Develops project ideas and creates opportunities to grow, enhance and expand current projects.
  • Submits proposals and contract amendment requests.
  • Negotiates contract terms and amendment requests with funders.
  • Reviews contracts received by funders and ensures contract reviews are conducted and documented by the review team. Addresses any concerns with funders prior to signing.
  • Contingent on funder signature requirements, signs proposal submission applications/documents, reports, new contracts, and contract amendments.

Financial Management:

  • Oversees the planning/creation of new contract budgets and oversees budget management for each designated project to ensure that Program Managers/Coordinators and partners are operating in alignment with expected quarterly/yearly expenditures.
  • Regularly meets with the Finance team to discuss fiscal needs and/or concerns.
  • Resolves financial challenges and issues as they arise to ensure fiscal responsibility.
  • Reviews and approves the quarterly funder reports for all programs and ensures they are signed prior to submission.
  • Carefully monitors all program budgets to ensure that financial targets and funder expectations are being met.
  • Approves and signs off on Program Manager/Coordinator expense reports and supplier invoices as needed.
  • Monitors program budgets to ensure accounting practices and funders’ budget stipulations are followed.

Evaluation and Reporting:

  • Produces and/or reviews, approves, and signs reports that meet funders’ expectations and meet The Career Foundation’s high-quality standards monthly, quarterly, and annually for funders and other project stakeholders.
  • Creates program evaluation tools, monitors customer service results, and develops annual evaluation reports.
  • Reviews Program Managers/Coordinators’ progress and performance reports and responds to comments, as necessary.
  • Oversees annual program audits to ensure funders’ expectations are met.
  • Ensures that quality assurance monitoring systems are in place to evaluate compliance related to client service, file documentation, budget management practices, and all policies and procedures at The Career Foundation.
  • Ensures that data capture systems are aligned across the organization and that accurate and timely internal reporting occurs which indicates project activities and progress towards goals; regularly uses data to contribute towards strategic decision-making and planning.
  • Organizes and prepares for funders’ site visits, including organizing the trainers, staff, participants, and partners.
  • Collects reports from project partners as necessary.

Partner Relations and Partner Contract Management:

  • Develops relationships with partners to enhance future project offerings.
  • Negotiates and sets up subcontracting agreements with project partners.
  • Supports Program Managers/Coordinators to ensure that partner contract expectations related to deliverables, reporting, and insurance are being met consistently.
  • Attends Employer/Sector Advisory meetings and other external partner meetings.
  • Supervises and motivates trainers, partners, and staff to reach targets and service expectations.
  • Trains and supports Program Managers/Coordinators with negotiating and mediating between partners, students and/or trainers as needed.
  • Receives feedback from the public, partners, trainers and participants, and resolves complaints.
  • Represents The Career Foundation at events, meetings, graduations, etc. as either an attendee or speaker as needed.

Government Relations:

  • Pitches new project ideas or program expansions to funders. 
  • Handles or oversees communications with funders, ensuring inquiries are responded to in a timely manner.
  • Prepares for and attends all funder audits with management and puts plans in place to ensure any recommendations for improvement are followed.
  • Coordinates tasks related to special requests from funders, such as handling a difficult client case.
  • Works with management to handle special requests to funders related to contracts, budgets, and program activities as needed.
  • Organizes contract amendments with funders as needed.


Qualifications/ Skills Required:

  • Post-secondary degree or an equivalent combination of education and experience is required.
  • Must possess a minimum of 7 + years’ progressive experience in a leadership and contract management role, ideally in the field of sector-specific employment, training and workforce development services. Budget and financial analysis knowledge is also required.
  • Demonstrated ability to strategically oversee project deliverables and lead teams to successful outcomes.
  • Demonstrated ability to manage staff and team performance effectively.
  • Demonstrated experience preparing proposals that generate funding.
  • Strong negotiation skills. 
  • Skilled at identifying opportunities, issues and solutions.
  • Experience managing/overseeing multiple teams and contracts, ideally in the employment and training services industry.
  • Experience in managing partner/stakeholder relationships, advisories, and committees.
  • Excellent organization, analytical, time management, and administrative skills.
  • Outstanding verbal and written communication skills.
  • Experience liaising with funders and other stakeholders.
  • Strong work ethic and flexible approach to support teams and meet deadlines.
  • Exceptional people skills and ability to uphold the organization’s service standards, policies, and core values.
  • A professional and courteous approach to client service with a high level of respect for the diversity of people served at The Career Foundation.
  • A demonstrated understanding of the value of inclusion, diversity, equity, and accessibility in the workplace.
  • High standards of ethics and confidentiality with proven ability to maintain sensitive information and exhibit tact, diplomacy, and good judgment.
  • Proficiency in Microsoft Office Suite (Word, PowerPoint, Excel), as well as Zoom and Outlook 365 applications, including Teams and SharePoint. Must also possess aptitude and willingness to learn and work with new online systems and technologies.
  • Capable of working under pressure with interruptions.
  • Responsive and flexible to evolving responsibilities and able to take initiative while maintaining a positive approach.
  • Willingness and flexibility to occasionally work outside of normal business hours during peak periods, when required.
  • Willing to travel periodically as needed.


How to Apply:


Please visit the ‘Join Our Team’ page on our website at and select the position for which you would like to submit your application. You may complete the application form directly through our website. Qualified candidates will be contacted for an interview. No phone calls please. Thank you for your interest in The Career Foundation.



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.

Please Note: is not affiliated with and in no way endorses or vets the organization that posted this job. Any links posted within the job will take you to their external site where the same disclaimer applies.

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