CharityVillage

Facilitator / Employment Transition Coach - The Career Foundation

Aug 24, 2025
Toronto, Ontario
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
Program & Role Description:
The Career Foundation’s Readiness for Successful Employment Transition (ReSet) program is designed to help income-support recipients prepare for and successfully transition into employment. This program consists of two phases. Phase one focuses on helping participants recognize the barriers that prevent them from pursuing meaningful careers. Through employment readiness and life skills training and coaching, participants develop a new outlook and a strong interest in pursuing employment. As a result of phase one, clients successfully transition into phase two: the Integrated Employment Service. Phase two provides alumni support and coaching to ensure clients are equipped and motivated to strengthen their attachment to the labour market.

As a Facilitator/Employment Transition Coach, you will be an integral member of the program team, responsible for providing clients with inspirational group training on the value and impact that work can have on their professional, personal, and family lives. By facilitating engaging workshops and providing one-to-one coaching to clients, you will help them develop life skills and readiness to transition into active job search, which is the intended purpose of the ReSet program.

You will also perform other important work, including community outreach to recruit new eligible participants and promote the ReSet program within the communities that we serve. You will have individual targets to meet, contributing to the team’s overall goal of achieving successful outcomes for our clients.

Position type:
  • Full-time (37.5 hours per week) contract until March 31, 2026
Base Location and Travel Requirements:
  • This opportunity is based on-site at The Career Foundation’s York office, located at Weston Rd. & Lawrence Ave. W. The role also involves frequent local travel to employer sites, community partners, and other stakeholders within the communities we serve to support program activities such as outreach and workplace tours. Additionally, team members work on-site at our Scarborough (Kingston Rd. & Midland Ave.) and Toronto (Yonge St. & St. Clair Ave. E.) locations on a rotational basis to support program delivery.  
  • The successful candidate should possess a valid Ontario G driver’s licence and a reliable vehicle to perform the core deliverables of the position that require frequent local travel, including to locations not accessible by public transit.
Vulnerable Sector Check:
  • An offer of employment for this opportunity will be contingent on a Vulnerable Sector Check (VSC).
Start date:
  • As soon as possible
Reporting to:
  • Program Manager
Responsibilities include:
Workshop Facilitation
  • Designs and delivers engaging in-person workshops through interactive activities and discussions focused on changing mindsets, goal setting, dispelling myths about work, and progressing clients towards enrolling in an employment program.
  • Maintains an effective working relationship with participants when presenting workshops, ensuring clients with different learning styles and needs are accommodated, and conducting knowledge checks and feedback sessions to ensure reflection, progress, and continuous attendance.
  • Coordinates guest speakers, training opportunities, and group mentorship events to advance clients' learning, exposure, and networking.
  • Manages conflict or disruptions during workshops in a proactive, positive, and professional manner.
  • Facilitates direct coordination of services with employment service partners, ensuring clients successfully transition to Phase 2 of the program, which is active job search.
  • Follows up with each client to ensure their positive engagement in the job search program and provides support as needed.
  • Creates an alumni network and facilitates follow-up workshops, including life skills sessions that support active job search and job retention topics.
  • Performs other relevant duties as needed.
Employment Transition Coaching
  • Conducts accurate assessments of potential clients and their eligibility for the program.
  • Assesses the needs of program participants, identifies their barriers to program participation and employment, utilizing the prescribed processes and systems.
  • Develops customized service plans with appropriate coaching support and employment exposure to help them transition into active job search.
  • Provides one-to-one life skills coaching to participants, encouraging them to apply skills learned through workshops and progress to their goals and employment program participation.
  • Coaches and motivates participants during the program and follows up during the early phases of Phase 2, which involves active job search.
  • Utilizes systems and technologies provided by The Career Foundation to further support clients with achieving successful outcomes.
  • Partners with the employment program to support the clients' job search engagement and progress towards employment.
  • Performs other relevant duties as needed.
Outreach to Participants and Employers
  • Performs effective outreach to recruit eligible participants who have been receiving Ontario Works Income Support or have been unemployed for an extended time.
  • Presents the ReSet program to community partners and potential applicants, ensuring they understand the program objectives, which is to help them become ready to participate in active job search and employment programs.
  • Conducts outreach and cold calls to employers to promote the ReSet program and arranges guest speaking sessions, workplace tours and exposure opportunities, mentorships, and professional networking sessions.
  • Develops two new employer contacts each week and eight new employer contacts each month to generate work exposure opportunities for clients of the program.
  • Conducts accurate assessments of participants based on program eligibility requirements and ensures all mandatory intake forms are completed.
  • Supports the Program Manager in preparing communications about the program, including success stories and entries for annual reports.
  • Performs other relevant duties as needed.
Case Management & Documentation
  • Maintains case notes and participant files in compliance with internal policies and funder requirements.
  • Prepares and maintains documentation on intakes, referrals, participant attendance, suitability indicators, outcomes, and other required information.
  • Documents case notes, including participants’ experiences, challenges, and growth in the program.
  • Monitors participant progress with ongoing follow-up calls and meetings and ensures all appropriate documentation is recorded in online systems.
  • Provides the Program Manager with documentation for supports to be purchased for program participants.
  • Ensures that participant records and files are kept up-to-date and audit-ready.
  • Performs customer service and administrative functions, including document creation and file retrieval.
  • Performs other relevant duties as needed.
Qualifications/Skills Required:
  • Post-secondary degree or diploma in human services, social sciences, or a related field is highly preferred, or an equivalent combination of education and experience is required.
  • Must possess a minimum of three years of related experience in workshop facilitation, job coaching, or other hands-on experience that is directly transferable to the duties of the position.
  • Experience facilitating in-person workshops with high participant engagement and completion rates is considered an asset.
  • Must be willing to work on-site full-time, with regular local travel to other offices, as well as to community partner locations, employer sites, and other stakeholder locations.
  • Must possess a valid Ontario G driver’s licence and a reliable vehicle to conduct frequent local travel required to meet the core deliverables of the position, including travel between sites and outreach in all communities served, including locations not accessible by transit.
  • Candidates who possess the above qualifications and direct experience working with long-term unemployed clients or those receiving government income support will be prioritized.
  • Prior experience working with multi-barriered job seekers and/or experience in government-funded employment programs is considered a strong asset.
  • Life Skills Coaching Certification is considered an asset.
  • Exceptional relationship development skills and the ability to develop rapport with people in all stakeholder groups, including program participants, employers, and community partners.
  • Must be results-driven in nature with a demonstrated ability to achieve targets.
  • Flexibility and adaptability to work effectively with a diverse population and the challenges they face.
  • Exceptional customer service skills and the ability to uphold the organization’s service standards, policies, and core values.
  • Demonstrated organizational skills, effective time management, and ability to multi-task to meet deadlines and achieve objectives.
  • A 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 tact, diplomacy, and good judgment.
  • Advanced proficiency in Microsoft Office Suite (Word, PowerPoint, Excel) and Outlook 365 applications, including Teams and SharePoint.
  • Must possess the aptitude and willingness to learn and work with new online systems and technologies.
  • Willingness and flexibility to occasionally work outside regular business hours when required to ensure the team meets all objectives.
  • Positive attitude with a dedicated work ethic and a willingness to take initiative to lend assistance where needed to help lead clients to successful outcomes.
This job is from CharityVillage
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