Retention Specialist

Costi•Mississauga, ON

3d•CA$63,000 - CA$70,000•Onsite

About The Position

This is a full-time union position scheduled to work 35 hours per week. This is a fully on-site position with no remote or hybrid options, due to funder and role requirements. Position Summary: The Retention Specialist is an integral part of a mission- and results-driven employment services team responsible for supporting individuals in achieving and sustaining meaningful employment. Reporting to the Regional Site Manager/ Site Manager and/or Assistant Site Manager, this role engages with clients and employers from the offer stage through onboarding and throughout the retention lifecycle, identifying risks to job retention, resolving conflicts, and applying strong problem-solving, negotiation, and patience to support long-term employment success. Operating in a structured, performance-driven environment, the Retention Specialist is accountable for retention targets and program outcomes, while also serving as a key service integrator who identifies client needs and facilitates timely referrals to COSTI programs and community resources. This position requires a professional, approachable manner, flexible working hours including evenings and weekends. The Retention Specialist consistently demonstrates a professional, approachable, and engaging manner, fostering a welcoming environment for all individuals accessing services, including job seekers, employers, and community partners, and maintaining a strong commitment to service excellence. Maintain flexible working hours, including evenings and weekends, to better connect with clients and accommodate their availability. This position requires in-office presence. PRIMARY ACCOUNTABILITY: To ensure sustained employment outcomes by providing structured, ongoing support to both clients and employers, while proactively identifying and addressing risks that may impact long-term job retention.

Requirements

Post-secondary diploma or degree in Social Services, Career Development, or related field, or equivalent experience.
Minimum of one (1) to three (3) years of experience in employment counselling or career advising.
Experience working with diverse client populations, including individuals facing barriers to employment.
Strong problem solver with the ability to identify barriers quickly and develop practical solutions.
Skilled negotiator who can de-escalate issues before they become conflicts and support effective resolution.
Demonstrates patience, professionalism, and strong interpersonal judgment when working with clients, employers, and partners.
Strong knowledge of job search strategies, employment programs, and labour market trends.
Demonstrated ability to conduct assessments, develop employment plans, and facilitate group coaching and training sessions.
Strong communication, facilitation, and interpersonal skills.
Fully on-site position with 100% in-office presence, five (5) days a week.
No hybrid or remote work options due to funder and position requirements.
Client-Centered Communication & Relationship Building: Builds trust through empathetic, professional, and effective communication with diverse clients and partners.
Facilitation, Collaboration & Interpersonal Skills: Engages individuals and groups while working collaboratively to support integrated service delivery.
Problem-Solving, Judgment & Adaptability: Applies critical thinking and sound judgment to address client needs in a dynamic environment.
Accountability, Organization & Results Orientation: Manages priorities effectively while delivering accurate, high-quality work and achieving performance targets.
Experience and knowledge of case management and client information systems, including systems such as CaseFLO, FFAI CaMS / EOIS CaMS, CIS, and related internal tracking systems.
Knowledge of Microsoft Office / Microsoft Office Suite, including commonly referenced tools such as Word, Excel, PowerPoint, and email.
Knowledge of virtual collaboration and service-delivery tools, especially MS Teams, Moodle other online tools used for workshops, coaching, and service delivery.
Knowledge of internet-based and online tools, including online employment tools, online service platforms, and web-based resources.
Knowledge of databases, reporting tools, and data-entry systems used for documentation, tracking, reporting, and performance monitoring.
Ability and willingness to learn new technologies, systems, databases, and digital tools as required for service delivery and reporting.
Aptitude and willingness to learn and work with new online, digital systems, databases, and technologies.
Must be willing to provide itinerant services and work regularly across multiple locations throughout the GTA, based on program and partnership requirements.
Required to provide a valid Vulnerable Sector Screening (VSS) Police check completed within the past 6 months.

Nice To Haves

Retention Management & Follow-Up Monitors employment stability, conducts structured follow-ups, and supports achievement of retention outcomes.
Client Support & Intervention Provides proactive coaching and resolves workplace challenges to sustain employment.
Employer Relations & Support Engages employers to support onboarding, address issues, and promote successful workplace integration.
Risk Identification & Problem Solving Identifies early retention risks and implements timely, practical interventions.
Service Navigation & Coordination Connects clients to appropriate supports and collaborates with internal teams to ensure continuity of service.
Performance, Documentation & Compliance Achieves targets while maintaining accurate records and meeting all program and audit requirements.
Technology Proficiency (CaseFLO, CaMS, Excel, PowerPoint, Word)
Client-Service Orientation: Delivers respectful, empathetic, responsive, and high-quality service to participants, employers, and partners.
Individualized, Person-Centred Support: Provides custom-tailored, flexible, one-on-one support tailored to each participant’s goals, strengths, and barriers.
Participant- and Employer-Centred Employment Success: Builds strong participant and employer relationships to support quality job matches and successful employment outcomes.
Responsive, Equitable, and Solutions-Focused Service Delivery: Applies fairness, sound judgment, and practical problem-solving to deliver consistent, accountable, participant-centred service.
Welcoming, Engaging, and Uplifting Service Experience: Creates a friendly, inclusive, and motivating environment that builds trust and encourages participant engagement.
Whole-Person, Integrated Service Navigation: Connects and integrates services to support the full range of participant needs and enable sustainable employment outcomes.

Responsibilities

Maintain a thorough understanding of organizational policies, program requirements, and contractual obligations, including retention-related performance targets and outcome expectations.
Ensure all activities are delivered in accordance with Employment Ontario (EO), IES guidelines, and internal service standards.
Engage with clients and employers at the offer stage to support successful onboarding and transition into employment.
Provide guidance to clients on workplace expectations, communication, and job readiness as they begin employment.
Support employers in onboarding new hires, including clarifying expectations and supporting effective workplace integration.
Conduct scheduled post-employment follow-ups with clients and employers at defined intervals, including 1,3,6 and 12 months, in accordance with WCG, IES and EO requirements.
Maintain consistent communication to monitor employment stability, satisfaction, and integration.
Identify retention risks early and refer clients to Career Advisors or Employment Consultants for timely intervention.
Document all follow-up activities, employment status changes, and supports provided accurately and in a timely manner.
Track job sustainment outcomes to support performance reporting, Success Measures, and contractual requirements.
Plan and deliver engaging individualized and group coaching sessions on a daily/weekly basis that support clients for employment by addressing potential workplace challenges and building the confidence and soft skills needed to succeed in a work environment including job retention topics such as, including dealing with conflict in the workplace, understanding workplace culture, email and workplace communication and interpersonal skills.
Facilitate both single-session and multi-week job retention group coaching sessions using in-person and virtual formats, using online tools to enhance engagement, accessibility, and learning outcomes.
Manage all event logistics, including preparation of training spaces, setup of materials and equipment, and room reset following sessions.
Track and analyze group coaching session enrollment, attendance, and client feedback to evaluate effectiveness, measure satisfaction, and support continuous improvement.
Provide individualized coaching and support to clients experiencing workplace challenges, including performance issues, interpersonal conflicts, or external barriers.
Support clients in accessing additional services and resources where required.
Maintain ongoing communication with employers to monitor employee performance and satisfaction.
Provide timely and customer service and professional support to address workplace concerns, including communication or performance challenges.
Conduct worksite visits where appropriate to support retention outcomes and strengthen employer relationships.
Monitor client progress and proactively implement strategies to support long-term employment retention.
Secure and document proof of employment and retention milestones as required.
Ensure all case files reflect accurate and up-to-date retention activities and outcomes.
Participate in case conferences, team meetings, and service planning discussions.
Collaborate with Career Advisors and Job Developers to ensure seamless service delivery and transitions.
Contribute to coordinated, team-based approaches to client success.
Update client records in CaseFLO, FFAI, CaMS, CIS, and internal tracking systems with accuracy and timeliness.
Maintain complete, accurate, and timely documentation of all client and employer interactions daily.
Maintain confidentiality and adhere to privacy legislation and EO guidelines.
Ensure all documentation meets audit, compliance, and funding requirements.
Contribute to reporting on retention outcomes, follow-up activities, and performance metrics.
Refer clients to training programs, education pathways, and community supports based on assessed needs.
Refer clients to other supports provided by COSTI, and to the community as required.
Assist clients in accessing appropriate financial support training opportunities and complete required financial support documentation.
Collaborate with internal staff (e.g., Job Developers) to ensure client readiness for job matching and placement.
Maintain accurate, timely, and complete case notes and service records in accordance with funder requirements.
Document all client interactions, progress, and outcomes in required systems (e.g., CaseFLO, CaMS).
Ensure compliance with program guidelines, audit requirements, and privacy standards.
Provide backup support across the intake-to-retention continuum, as required by caseload demands, to ensure service continuity and program outcomes, within the scope of the role.
Achieve individual service delivery targets, including client volumes, group coaching delivery, and retention reporting.
Maintain accurate, complete, and timely data entry for all client monitoring and employer retention activities, including employer engagement tracking, client follow-up retention tracking (1,3, 6 and 12 months), service interventions, group coaching sessions participation, referrals, employment outcomes, and follow-up activities in required systems (e.g., CaseFLO, FFAI, CaMS, CIMS).
Track, monitor, and report on key performance indicators, including service volumes, client progress, and employment outcomes, and adjust service delivery approaches as needed to meet program targets.
Prepare and contribute to statistical and narrative reporting, including activity summaries, service outcomes, and performance reviews, in accordance with program and organizational requirements.
Participate actively in performance accountability processes, including daily, weekly, monthly, quarterly, and annual performance meetings and the annual learning retreat.
Demonstrate accountability for individual and team performance outcomes, ensuring alignment with funder expectations and organizational standards.
Engage in ongoing learning and professional development, including participation in training sessions, knowledge-sharing activities, and continuous improvement initiatives throughout the year.
Gather success stories and testimonials of placements and share with site management and communications team.