Retention Specialist

POSITION TYPE: Full-Time

DEPARTMENT:Employment Center

AFFILIATION:Unionized Position

LOCATION:North York, ON

HOURS:Mon-Fri, 7 hours per day

EXTENDED HOURS: Dependent on needs of the program

SALARY: $28.49

START DATE: December 1, 2025

About the Organization

For over 45 years, Tropicana has been a pillar of strength and support, proudly standing as one of Canada's largest Black-led, Black-serving, and Black-focused organizations. Our mission is to provide access to opportunities that lead to personal success and positive life decisions for Black, African, and Caribbean individuals, as well as others facing barriers. This includes those who experience challenges in education, language, finances, and social circumstances.

We are dedicated to empowering our community through culturally responsive services in education, employment,and community development. Tropicana is committed to making a lasting impact, with programs designed to address the unique needs of the populations we serve. Our motto, "We Change Lives," reflects our unwavering commitment to driving meaningful change for those we support.

About the Position

The Client Focused - Retention Specialist plays a critical role in strengthening client relationships and ensuring successful, long-term employment outcomes for all stream clients. This position provides ongoing support, mentoring, and coaching to clients after they secure employment, with a focus on promoting engagement, resolving concerns, and fostering self-sufficiency.


Areas of Responsibility

Client Services:

  • Provide mentoring and on-the-job coaching to both clients and employers, promoting successful workplace integration
  • Build and maintain strong relationships with clients, fostering rapport and enhancing their soft skills for long-term success
  • Deliver consistent, reliable support by responding promptly and effectively to client needs
  • Address workplace crises swiftly, offering tailored training on workplace expectations and providing on-the-job coaching to resolve challenges
  • Manage a caseload of clients to ensure successful progression toward one year of sustained employment, meeting funder Key Performance Indicators (KPIs)
  • Provide offsite retention services as needed to accommodate clients' work schedules
  • Deliver individual and group career coaching sessions focused on successful job performance and career advancement
  • Offer referrals to childcare, healthcare, mental health services, and other resources to support long-term employment retention and career growth
  • Maintain regular client contact via phone, email, ensuring timely follow-ups in alignment with funder guidelines
  • Engage with clients using customer service principles to meet performance-based funding goals, program targets, and reporting deadlines
  • Assess client needs promptly and collaborate with the Employment Consultants and Job Developers to provide additional support, resources, and referrals
  • Support clients requiring additional job retention coaching by offering guidance and relevant referrals
  • Educate clients on online tools and resources to enhance work sustainability
  • Provide information on job search strategies, workplace expectations, and adapting to changes in workplace settings

Employer Services:

  • Educate employers on program requirements, promoting an understanding of decent work principles and workplace standards.
  • Advocate for clients with employers, addressing concerns and facilitating conflict resolution to support workplace integration and success.
  • Demonstrate strong knowledge of the Accessibility for Ontarians with Disabilities Act (AODA), employment law, and the Employment Standards Act (ESA) to support compliance and best practices.

Administrative:

  • Collect and verify clients paystubs and attestations, ensuring timely and accurate upload to the FFAI system
  • Complete file closures data entry requirement on approval
  • Assist with quality control of client files by verifying accuracy of data entered and notifying Manager of discrepancies/concerns
  • Gather, review, input, and assess client and service information in alignment with Service Delivery Guidelines

Client Assessment and Resource Knowledge:

  • Ability to conduct and interpret client assessments to identify individual needs, provide coaching and mentoring, and support clients from diverse cultural backgrounds and with complex barriers
  • Stay informed about the local labour market, community resources, government programs, job search techniques, career development strategies, and issues related to unemployment to better assist clients
  • Provide professional resume writing, career coaching, personalized goal setting and planning for clients

Other Duties

  • Proactively contributes to the organization.
  • Initiates or assists with other projects as required

Skills and Qualifications

  • A post-secondary diploma/degree in a relevant discipline, which may include Social Work, Human Resources, Career Counselling, or related and two years' service experience in job coaching, mentoring, and retention with individuals facing complex barriers to employment or a combined equivalent education and experience
  • Demonstrated ability to work with marginalized and diverse groups, including barriered youth, newcomers, Indigenous persons, individuals with disabilities, and those experiencing mental health or addiction challenges
  • Excellent technology skills (MS Office Suite, DocuSign, Adobe Acrobat, etc.), experience using client/customer databases and aptitude to learn new technologies autonomously
  • Excellent communication skills, both verbal and written
  • Ability to follow guidelines and procedures for standardized outputs
  • Proven ability to act professionally and maintain confidentiality, ensuring sensitivity to the needs and interests of clients
  • Proven organizational skills coupled with the ability to handle multiple tasks, meet deadlines, and report on the status of work when requested
  • Proven ability to apply sound judgement and work with limited supervision
  • Experience in effectively and creatively connecting clients to employers based on mutual needs/benefits
  • Ability to achieve program goals/targets including planning ahead for contingencies and identifying solutions to problems to ensure best results
  • Second language an asset

Although we appreciate each application, only those candidates being considered for the position will be contacted.

Tropicana Community Services commits to promoting inclusion, diversity, equity, and access (IDEA) through its information and support, advocacy, programming, internal policies, and governance structures. Tropicana Community Services will aim to ensure that our staff reflect the experience, skills and diversity of the communities we serve and create an inclusive, barrier-free work environment, beginning with the recruitment process. If you have restrictions that need to be accommodated to fully participate in any phase of the recruitment process, please contact Human Resources. All information received in relation to accommodation will be kept confidential.

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