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Job Description

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

Program and Role description: This program provides eligible participants with a 14-week pre-employment and skills development training model that integrates technology, sales and high-performance workplace skills to prepare women for future-oriented careers across Ontario and British Columbia.  Participants will consist of women, including those who are immigrants, women with disabilities, self-identifying LGBTQ2 individuals, and those who have experienced prolonged unemployment.  The program team will also work closely with employers to conduct Gender Based Analysis (GBA+) workplace and policy assessments and to deliver Gender Equity and Inclusion training.

The Outreach/Wraparound Support Worker is an integral part of the team, responsible for recruiting eligible participants into the program, finding appropriate job placement opportunities for program participants, and facilitating wraparound supports to ensure their success. The Outreach/Wraparound Support Worker will also be responsible for establishing new relationships with employers, and other essential duties.  

  • Position Type: This will be a full-time, one-year contract with good possibility to lead to permanent employment and is currently contingent on program funding that is anticipated to commence on April 1, 2022.
  • Reporting to: Program Coordinator
  • Location(s):  This will be a hybrid-remote position comprised of on-site work at a base office in Toronto, ON, work-from-home functions, and travel between other sites across the Greater Toronto Area. Schedule will be as determined by management. Must have valid G driver’s licence and access to reliable vehicle for work-related travel, and appropriate work-from-home space with high-speed internet connection.
  • Number of positions: 1
  • Experience: 2 + years
  • Start date: April 2022

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.


Responsibilities include but are not limited to:

Outreach, Program Promotion & Participant Recruitment:

  • Presents the program to community partners and applicants in Ontario and British Columbia, ensuring that they understand the program components, objectives, and time requirements.
  • Conducts assessments of applicants based on program eligibility requirements and ensures that all mandatory intake forms are completed.
  • Recruits eligible and suitable participants for the program via numerous methods, including outreach to community partners, utilization of job boards, social media campaigns, etc.
  • Screens applications for eligibility and suitability factors, schedules interviews, conducts intake sessions, and facilitates numerous information sessions.
  • Other duties as assigned.

Wraparound and Individual Support:

  • Assesses clients’ employment goals and co-designs suitable individual action plans
  • Coordinates wraparound services with community partners to meet participant needs.
  • Provides information and referral services to other community programs as necessary.
  • Contacts candidates to extend offers or communicate regrets and refers those not selected to other appropriate services.
  • Liaises with community partners regarding client referrals and client progress as needed.
  • Provides participants with program overview and outline of training components.
  • Provides one-on-one support and/or group counselling to participants on employment-related topics, such as job search, employer research, marketing skills, conflict resolution, career advancement, accepting feedback, etc.
  • Identifies barriers to employment and provides participants with suitable referrals as needed.
  • Assists participants in the exploration of employment requirements, industry accreditation, and further education/training opportunities.
  • Supports participants in planning and conducting effective job search strategies.  
  • Collects and monitors program data regarding participants’ attendance, case plans, training status, training outcomes, employment status, employment outcomes, etc.
  • Maintains documentation of participant files and records of service, including participant progress reports, in internal and funder-mandated systems.
  • Creates case files in databases for all participants, including entering data pertaining to education, work history, NAICS and NOC numbers.
  • Ensures that 80% of participants who start training complete all training components, including job placements.
  • Other duties as assigned.

Pre-Employment Workshop Facilitation:

  • Researches and develops content for pre-employment workshops in collaboration with the Program Coordinator.
  • Facilitates and delivers engaging workshops catered to Tech-forward careers, both online and in-person.
  • Provides industry-specific orientation to the workplace and employer expectations.
  • Coordinates and schedules external training with training partners and industry guest speakers.
  • Professionally presents information to participants on topics including employment roles, effective job search strategies, job posting analysis, cold calling, resume and cover letter writing, interview skills, and appropriate workplace behaviour.
  • Resolves scheduling conflicts and participant disruptions during workshops, as needed, in a proactive and professional manner.
  • Regularly monitors personal performance against program targets to ensure the achievement of expected results for the project.
  • Other duties as assigned.

Job Retention Services / Job Development:

  • Conducts outreaching to employers and secures placements for participants.
  • Coaches participants in job placements to ensure job retention.
  • Mediates on-the-job conflict between employers and participants as needed.
  • Advises employed participants on career laddering opportunities and plans next steps.
  • Provides on-going job placement services as required.
  • Completes weekly check-ins with participants while in work experience.
  • Purchases and distributes participant support items.
  • Other duties as assigned.


  • Post-secondary degree or diploma in human services or related field is required, or equivalent combination of education and experience.
  • Must possess a minimum of 2 years’ transferrable experience in workshop facilitation, community outreach, recruitment, and/or sales and marketing.
  • Experience with employment counselling, public speaking, and workshop facilitation considered an asset. Candidates who possess the above qualifications as well as previous resume and cover letter writing experience will be given preference.
  • Knowledge or experience in IT, Sales, Marketing or Business and an understanding of the unique needs of women seeking access into these fields, considered a strong asset.
  • Exceptional relationship-building skills in order to establish connections with employers and community partners in Ontario and British Columbia, is required.
  • Excellent workshop facilitation skills with proven ability to maintain participant engagement.
  • Knowledge of adult learning principles considered an asset.
  • A professional and courteous approach to client service with a high level of respect for the diversity of the people served, including participants who face barriers to employment.
  • Must be results-driven in nature in order to achieve program goals and targets.
  • Knowledge of current labour market trends, the impact of COVID-19 on the labour market, job search techniques, and employment research methods.
  • Excellent verbal and written English communication skills with ability to clearly communicate information verbally and in writing.
  • Advanced proficiency in Microsoft Office Suite (Word, PowerPoint, Excel), as well as Zoom, and Outlook 365 applications, including Teams, SharePoint, Forms, and Bookings. Must also possess aptitude and willingness to learn and work with new online systems and technologies.
  • Exceptional customer service skills and ability to uphold the organization’s service standards, policies, and core values.
  • Outstanding organizational skills, time management, and ability to multi-task in order to meet deadlines and achieve program targets and objectives.
  • Punctual, self-motivated and self-directed.
  • Willingness to step-in to assist team members as needed to help ensure program goals are met.
  • Ability to maintain sensitive information, exhibit tact, diplomacy and good judgment, with high standards of professionalism, ethics and confidentiality when facing challenging situations.
  • Capable of working under pressure with frequent interruptions.
  • Ability to build strong working team relationships.
  • Must be able to work from base office location in Toronto, ON, and travel between other locations in the GTA on a regular basis. Must possess a valid G driver’s licence and access to reliable vehicle for work-related travel.
  • Must be equipped to perform some job functions remotely from home with appropriate work-from-home space and high-speed internet connection.
  • Willingness and flexibility to occasionally work outside of normal business hours during peak periods, when required.
  • Must be fully vaccinated (two doses) against COVID-19. The successful candidate will be required to submit official documentation to confirm vaccination status prior to job offer.

Application Form

To apply for this position, please complete the application form below. We suggest using the latest version of Google Chrome or Microsoft Edge to complete the form, in order to ensure that your application is submitted correctly. 

*Should you experience any technical difficulties while submitting your application, please submit your résumé to jobs@careerfoundation.org, along with a Word document that addresses all of the questions in the application form.

About The Career Foundation

The Career Foundation offers a wide range of career and job-related programs. 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. For more information please visit our website at www.CareerFoundation.com.

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.

We are a professional, result-driven organization that has been described by our employees as caring, compassionate, innovative, and team-oriented.

We also offer:

  • Competitive compensation
  • A comprehensive health benefits plan that includes massage therapy, naturopath services, and travel coverage
  • An Employee & Family Assistance Program
  • An RRSP matching plan
  • A wellness program
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