BenefitsCompetitive compensationA comprehensive health benefits plan that includes massage therapy, naturopath services, travel coverage, and much moreA comprehensive dental insurance planAn RRSP Matching benefitAn Employee & Family Assistance programEmployee wellness initiativesPaid days off for religious observance purposesPaid days off for personal wellness purposesProgram and Role DescriptionThe Career Foundation operates five full suite Integrated Employment Services (IES) Centres across the Greater Toronto Area (GTA). 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.Role Title: Career Retention Specialist. As a Career Retention Specialist, you will support clients and employers following successful job placements to ensure long‑term employment stability and positive workplace outcomes. You will manage 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. You will meet ongoing individual targets that contribute to the team’s collective ability to fulfill contracts with our funder and guide clients toward successful outcomes.Position TypeFull‑time (37.5 hours per week) one‑year contract with excellent potential for permanency.Starting Salary$57,000.00 annually, or $58,000.00 if the candidate holds a master’s degree, both languages proficiency in French, or full proficiency in Sign Language.Base Location and Travel RequirementsScarfield Employment Centre, near Kingston Road & Midland Avenue. Requires periodic travel to other locations, including employer sites and stakeholder locations. Hybrid schedule allowed: one work from home day per week, subject to operational requirements.Vacancy StatusExisting vacancy.StartAs soon as possible.Reporting ToArea Manager, Employment and Placement Services.Vulnerable Sector CheckOffer contingent on acceptable Vulnerable Sector Check.Use of Artificial IntelligenceArtificial Intelligence is not used to screen, assess, or select applicants.ResponsibilitiesRetention Monitoring, Mandatory Checkpoints, and Post‑Placement Client SupportConduct structured post‑placement follow‑ups with mandatory 3‑month, 6‑month, and 12‑month checkpoints.Maintain ongoing rapport with employed clients,



applying consistent engagement to develop trust.Provide coaching and support to assigned clients, helping them adjust to workplace expectations.Monitor client progress between checkpoints to identify early signs of retention risk and implement timely interventions.Support clients in developing workplace communication, problem solving, and conflict resolution skills.Identify challenges affecting clients’ employment retention and develop solutions to prevent job loss.Encourage client confidence, motivation, and accountability to support long‑term employment success and career progression.Plan and facilitate job retention workshops.Perform other relevant duties as assigned.Retention Tracking and Service ContinuityOwn communication with clients entering the retention phase, ensuring seamless handoff from team members who facilitated placement.Confirm job start details, including employer information, start dates, and employment status.Communicate regularly with internal team members for accurate tracking and reporting of job starts and retention outcomes.Enter and maintain accurate and up‑to‑date client employment status, follow‑up communications, required checkpoints, and other outcomes within mandatory online reporting systems.Perform other relevant duties as assigned.Employer Follow‑Up and Workplace Relationship ManagementBuild and nurture strong employer relationships that foster long‑term partnerships.Maintain ongoing communication with employers to monitor performance of placed clients.Provide guidance to employers to support onboarding, workplace integration, and employee success.Collaborate with employers to address workplace challenges, including resolving issues that may impact job retention.Facilitate communication between clients and employers to ensure constructive and timely resolution of concerns.Perform other relevant duties as assigned.Administration and Data ManagementDocument all retention milestones, follow‑ups, interactions with clients and employer partners, retention plans, coaching sessions, and required checkpoint data within mandatory online reporting systems.Collaborate with team members to ensure accurate and consistent data entry across reporting systems.Maintain strict confidentiality of client and employer information in accordance with privacy and security protocols.Provide reports to management related to retention outcomes, checkpoint completion,



and other program data.Perform other relevant duties as assigned.Quality Support and ReportingComplete quality assurance activities, including file reviews, audit preparation, and compliance monitoring.Support team members with post‑employment case management, ensuring documentation and compliance requirements are met.Contribute to continuous improvement activities to enhance service delivery and retention outcomes.Perform other relevant duties as assigned.QualificationsPost‑secondary degree or diploma in Career Services, Social Services, or another related field, or an equivalent combination of education and experience.Minimum of two years’ experience in employment services, career coaching, case management, or directly transferable experience.Strong coaching and client support skills.Proven track record in a results‑driven environment, meeting targets.Strong data entry accuracy, highly organized, capable of managing multiple client follow‑ups.Excellent verbal and written English communication skills; fluency in a second language is an asset.Experience supporting individuals facing barriers to employment and working within government‑funded programs is an asset.Exceptional relationship‑building skills, with a proven ability to develop rapport with diverse stakeholders.Demonstrated understanding of workplace expectations, employment standards, and employer practices.High emotional intelligence, demonstrating patience, empathy, and connection.Exceptional customer service skills and the ability to uphold the organization’s service standards.High ethical and confidentiality standards, with proven experience handling sensitive information.Excellent time management and organizational skills, able to multitask and meet deadlines.Strong problem solving and conflict resolution skills.Proficiency in Microsoft Office Suite and Microsoft 365 applications.Demonstrated aptitude for learning new technologies and systems; prior experience using case management systems is a strong asset.Flexibility to work outside regular business hours, including evenings and weekends.Solid work ethic, with a positive and proactive attitude.Demonstrated ability to remain flexible, resilient, and adaptive.EEO StatementThe 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 orientations. In accordance with the Accessibility for Ontarians with Disabilities Act (AODA), we are also committed to accommodating applicants with disabilities throughout the recruitment process.#J-18808-Ljbffr

📌 Career Retention Specialist - $57,000 - $58,000 A Year (Winnipeg)
🏢 The Career Foundation
📍 Winnipeg