Career Retention Specialist

About The Career Foundation:

The Career Foundation is a dynamic non-profit organization and registered charity that offers a wide range of employment, training, and workforce development services to job seekers and employers. Since its inception in 1988, The Career Foundation has steadily expanded its services. Operating out of seven locations in the Greater Toronto Hamilton Area, as well as offices in British Columbia, Alberta, and Nova Scotia, we now help thousands of people each year successfully achieve 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 and Role Description:

The Career Foundation operates five full suite Integrated Employment Services (IES) Centres across the Greater Toronto Area (GTA), conveniently located in Etobicoke, North York, Toronto, York, and Scarborough. These centres provide job seekers with a comprehensive range of services, including career exploration, résumé and interview preparation, job search support, employer connections, and employment retention support. The Career Foundation also partners with employers that share our commitment to community hiring. Employer services include access to a diverse talent pool, support with coordinating and hosting hiring events, guidance on how to effectively coach and support new hires, and strategies to support job retention.

Career Retention Specialist

As a Career Retention Specialist, you will fulfill a critical role in the Start & Succeed phase of the Integrated Employment Services (IES) client journey by supporting clients and employers following successful job placements to ensure long-term employment stability and positive workplace outcomes. This role assumes primary responsibility for clients who have been successfully placed into employment, ensuring a seamless handoff from other team members who helped facilitate their employment outcome.

You will be responsible for managing the retention phase of the client journey, maintaining ongoing relationships with employed clients and employers, and ensuring that successful employment outcomes are sustained over time. Additionally, you will be responsible for meeting ongoing individual targets relevant to your position, which contribute to the team’s collective ability to fulfill all contractual obligations with our funder and guide clients toward successful outcomes.

As the ideal candidate, you are a relationship-focused professional who is committed to supporting clients in achieving long-term employment success. You proactively identify and address barriers, coordinate supports, and provide ongoing follow-up to help prevent job loss. You also have strong interpersonal and conflict resolution skills, combined with the technical proficiency, organizational skills, and attention to detail needed to ensure accurate documentation and reporting within required digital systems.

Position Type:

Full-time (37.5 hours per week) one-year contract with excellent potential for permanency.

Starting Salary:

The starting annual salary for this position is $57,000.00 (or $58k if the successful candidate holds a master’s degree, full bilingualism in French, or full proficiency in Sign Language).

Base Location and Hours of Work:

This opportunity is based at The Career Foundation’s Central Toronto Employment Centre, located near Yonge & St. Clair Avenue East, and requires periodic travel to other locations as needed, including employer sites and other stakeholder locations. The successful candidate must be willing to work on site from the office on a full time basis. The position will also permit a hybrid schedule, allowing for one work from home day per week. The hybrid schedule is based on performance and operational requirements and is therefore subject to change at any time.

Please also note that, in order to effectively support our employed clients who work standard full-time business hours, the Career Retention Specialist position requires availability to work evening and weekend hours to ensure accessibility to these clients.

Vacancy Status:

This posting is for an existing vacancy.

Start:

As soon as possible.

Reporting to:

Area Manager, Employment and Placement Services

Vulnerable Sector Check:

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

Use of Artificial Intelligence:

Artificial Intelligence (AI) is not currently used to screen, assess, or select applicants at any stage of the hiring process.

Responsibilities include:

Retention Monitoring, Mandatory Checkpoints, and Post-Placement Client Support

• Conducts structured post placement follow ups with clients, including mandatory 3 month, 6 month, and 12 month checkpoints to monitor and support employment stability, job satisfaction, and long term outcomes.
• Maintains ongoing rapport with employed clients, applying consistent engagement to develop trust and rapport and to provide proactive support throughout the retention period.
• Provides ongoing coaching and support to assigned clients, supporting them to adjust to workplace expectations, responsibilities, and work environments.
• Monitors client progress between checkpoints to identify early signs of retention risk and implements timely interventions to minimize job loss.
• Supports clients in developing workplace communication, problem solving, and conflict resolution skills.
• Identifies challenges affecting clients’ employment retention and proactively develops solutions to prevent job loss.
• Encourages client confidence, motivation, and accountability to support long term employment success and career progression.
• Plans and facilitates job retention workshops.
• Performs other relevant duties as assigned.

Retention Tracking and Service Continuity

• Takes ownership of communication with clients who have obtained employment and are entering the retention phase, ensuring a seamless handoff from team members who facilitated their employment outcomes to maintain continuity of service.
• Confirms job start details, including employer information, start dates, and employment status, ensuring accurate documentation and transition into retention services.
• Communicates regularly with internal team members to ensure accuracy in tracking and reporting job starts, retention outcomes, and program performance metrics.
• Enter and maintain accurate and up-to-date information on client employment status, follow-up communications, required checkpoints, and other outcomes within mandatory online reporting systems.
• Performs other relevant duties as assigned.

Employer Follow-Up and Workplace Relationship Management

• Builds and nurtures strong employer relationships that foster long-term partnerships and positive employment outcomes.
• Maintains ongoing communication with employers to monitor the performance of placed clients, including workplace integration and overall satisfaction.
• Provides guidance to employers to support onboarding, workplace integration, and employee success.
• Works collaboratively with employers to address workplace challenges, including resolving issues that may impact job retention.
• Facilitates communication between clients and employers to ensure constructive and timely resolution of concerns.
• Performs other relevant duties as assigned.

Administration, Quality Support, and Data Management

• Documents all retention milestones, follow-ups, interactions with clients and employer partners, retention plans, coaching sessions, and required checkpoint data within mandatory online reporting systems, ensuring compliance with funder requirements, audit readiness, and program standards.
• Collaborates with team members as needed to ensure accurate and consistent data entry across reporting systems, tracking all activities to meet deadlines and properly record outcomes.
• Maintains strict confidentiality of client and employer information in accordance with privacy and security protocols and policies.
• Provides reports to management, as assigned, related to retention outcomes, checkpoint completion, and other program data.
• Completes quality assurance activities, including file reviews, audit preparation, and compliance monitoring, ensuring adherence to funder and organizational requirements.
• Supports team members with post employment case management, ensuring documentation standards and compliance requirements are met.
• Contributes to continuous improvement activities to enhance service delivery and retention outcomes.
• Performs other relevant duties as assigned.

Qualifications/ Skills Required:

• Post secondary degree or diploma in Career Services, Social Services, or another related field relevant to the position’s duties is highly preferred, or an equivalent combination of education and experience is required.
• Minimum of two (2) years’ experience in employment services, career coaching, case management, or other directly transferable experience related to the position’s responsibilities is required.
• Solid coaching and client support skills, with the ability to guide clients through workplace challenges and support long term employment success.
• Proven track record in a results driven environment, with experience meeting targets.
• Strong data entry accuracy and attention to detail; highly organized and able to manage multiple client follow ups across different stages of the retention and monitoring process.
• Excellent verbal and written English communication skills, with the ability to clearly communicate information. Fluency in a second language is considered an asset.
• Experience supporting individuals facing barriers to employment and working within government funded employment programs is considered an asset.
• Exceptional relationship building skills, with a proven ability to develop rapport with individuals from diverse backgrounds and a range of stakeholder groups.
• Demonstrated understanding of workplace expectations, employment standards, and employer practices.
• High emotional intelligence, demonstrating patience, empathy, and connection when working with clients of varying experiences, needs, and abilities.
• Exceptional customer service skills and the ability to uphold the organization’s service standards, policies, and core values.
• High ethical and confidentiality standards, with proven experience handling sensitive information and demonstrating tact, diplomacy, and sound judgment.
• Excellent time management and organizational skills, with the ability to multitask, meet deadlines, and achieve targets and objectives.
• Strong problem solving and conflict resolution skills.
• Proficiency in Microsoft Office Suite and Microsoft 365 applications, including Outlook, Teams, and SharePoint.
• Demonstrated aptitude for learning new technologies and systems. Prior experience using case management systems (e.g., FFAI, CaMS) is considered a strong asset.
• Flexibility to work outside regular business hours, including evenings and weekends, to meet the core deliverables of the position.
• Strong work ethic, with the ability to multitask while maintaining a positive and proactive attitude.
• Demonstrated ability to remain flexible and resilient, adapting quickly to changing priorities while maintaining trust and positive working relationships.

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.