Retention Specialist### Retention SpecialistApply: 15-North York Centre: Full time: Posted 9 Days Ago: End Date: October 31, 2026 (2 days left to apply)Scheduled Weekly Hours:35Union:YesWork Shift:Remote Type:Duration:November 16, 2026-

Job Description
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 SummaryThe 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 skilled, 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 ACCOUNTABILITYTo 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 *Job Title*Retention Specialist*Function*Employment retention, Client and employer support, Job sustainment monitoring, Risk identification and intervention*Reports To*Regional Site Manager/ Site Manager and/or Assistant Site Manager*Purpose*To support clients and employers in sustaining successful employment outcomes by providing structured follow-up, early intervention, and ongoing retention support aligned with program and funding requirements.*Key Contribution*Maintains employment outcomes through proactive monitoring, coaching, and issue resolution, contributing to retention targets and performance metrics. Strengthens client stability and employer satisfaction by identifying risks early and implementing effective interventions.

KEY RESPONSIBILITIES
## Program Knowledge and Contractual Alignment
* 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.## Pre-Employment and Onboarding Support
* 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.## Structured Follow-Up and Monitoring
* 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.## Group Coaching Facilitation and Group Services
* 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 o

📌 Retention Specialist (Toronto)
🏢 Costi
📍 Toronto