Job Posting 100463

Engagement/Retention Specialist
Caledon Community Services
Halton / Peel area
Bolton, ON
closed 3 days ago (Wed, 10 Apr)
full time

Position Details:  Permanent Full-Time, 35 hours/week (Monday – Friday)

Location:  18 King Street East, Bolton ON (hybrid – combination of on-site and remote)         

Minimum On-site Work Requirement:  3 days/week

Deadline to Apply:  April 10, 2024  

Applicants are strongly encouraged to apply early; interviews may be conducted throughout the competition process.

Agency Overview: 

Throughout the entirety of the Town of Caledon, Caledon Community Services (CCS) is helping shape the future of a caring and engaged Caledon community.  Our social service programs address community needs in a uniquely challenging and increasingly diverse GTA community.  CCS is home to Caledon’s only accessible transportation program, the Exchange Community Hub that includes food supports and a range of activities, the Caledon Specialist Clinic, and personal support services for seniors. We offer settlement services and language classes for newcomers and comprehensive employment services for job seekers and local businesses. We provide paid training programs for Caledon youth as well as exciting internships and volunteer opportunities.  Finally, we invite the community to shop at Evolve, a retail shopping destination. We host a variety of fundraising events annually.  We invite you to volunteer with us. Proceeds raised support service delivery for many of our programs. The breadth of our services makes for compelling opportunities to attract new friends and raise support for our work. Learn more at 

Our Customer Service Vision:  Making it Easy to Ask, Participate and Give

Position Overview: 

The Engagement/Retention Specialist will primarily focus on providing pre-and post-employment services to assist jobseekers in addressing barriers to employment, through early intervention and retention support services to achieve sustainable employment. 


Position Deliverables/Accountabilities:  The Engagement/Retention Specialist is a member of the Employment and Training Division, Employment Services team. Under the general direction of the Director, Employment and Training the incumbent will be required to undertake general case management duties as required with specific focus on supporting client intake, monitoring clients progress and supporting retention by completing the below duties:

  • Provide services to Clients in a manner that is welcoming, safe and professional and ensures that their privacy rights are protected
  • Deliver services in line with CCS’ contract, guidelines, policies, procedures, and performance requirements
  • Use Case Management System to ensure all documentation is accurate, up to date and submitted within set timeframes
  • Manage workload while working towards Key Performance Indicators (KPIs) through prioritization and effective time management
  • Provide coaching, group facilitation and case management elements and related engagement/retention activities
  • Provide part or all aspects of the Employment Service model as needed
  • Display high level of personal integrity and professionalism when representing CCS
  • Other duties as required that will support Clients return to work


  • Develop and maintain relationships with community stakeholders as part of generating and managing Client referrals
  • Engage and follow up with program inquiries from multiple streams
  • Screen Clients to make the determination if a client is best served through unassisted, assisted and/or other Employment Services programs
  • Support Clients with intake, awareness and navigation support, including accessing community resources for additional support needed to improve their job readiness
  • Manage referrals and book assessments ensuring appropriate documentation in all case management systems; Provide supported referrals as needed


  • Work with an integrated service delivery and case management model including case conferencing to support employability and smooth transition into the workplace
  • Upon employment, monitors client and employer for job retention (at a minimum, or more frequently when required), securing feedback on service quality and long-term impact
  • Provides ongoing job maintenance support and follow-up with newly employed clients for up to 12 months
  • Provide one-to-one follow-up to address issues similar to re-employment or provide referral to further training and education and/or life skills
  • Obtains documentary evidence of employment (i.e., pay stub, attestation form, letter/email from employer) at job start, 1, 3, 6, and 12-months post job start
  • Manages client caseload, ensuring data is entered into case management systems (CaseFLO and CaMS)
  • Collaborates with the Employment Specialist/Job Development team to support clients who are not successful in retaining their paid employment or work placement to assist them in finding new employment. 

Resources and Information:

  • Provide ongoing support to incoming clients to the Resource Centre
  • Maintain and update print and electronic materials in the Resource Centre
  • Support scheduling of events and prepare materials for information sessions/workshops and promotional purposes, and support social media promotion
  • Assist clients onsite with computer access, including internet-based services
  • Support front reception services and general as needed
  • Participate in the hosting of community and employer events 


  • Participate in a team approach to ensure effective and co-operative functioning across the division and all specialists
  • Support and maintain online job bank and social media accounts as required
  • Provide administrative support (client tracking, supports, incentives, reports) as required
  • Participate in staff and community meetings deemed appropriate by the Division Director
  • Travels and works off-site as assigned; Other duties as assigned 

Qualification Criteria:

  • 2-year college diploma in a related field such as Administration, Social Service Work, Career and Work Counseling
  • 1 to 2 years related experience
  • Demonstrated experience in some or all aspects of Job Search or Job Retention including employment/coaching
  • Demonstrated understanding of community resources, programs and employment services
  • Proficiency in working with computers, databases, Microsoft Office 365 (web) and various digital platforms including Google, Zoom, Teams, etc.
  • Effective Communicator; Excellent interpersonal, analytical, communication and teamwork skills
  • Committed to working with a team to build a great customer experience
  • Passionate about helping others
  • Presentation/facilitating and coaching skills
  • Access to a vehicle, valid driver’s license and insurance;
  • Access to a personal device (smart phone or tablet) is required for periodic, two-factor authentication using the Microsoft Authenticator App when signing into CCS networks/cloud environment as part of I.T. security protocols.
  • Satisfactory Criminal Records Check.

We thank all applicants for their interest but will only be contacting those selected to attend an interview. CCS is an equal opportunity employer encouraging applications from qualified individuals from diverse groups including Indigenous peoples, visible minorities, persons with disabilities, persons of all sexual orientation or gender identity and other grounds identified under the Ontario Human Rights Code.  CCS will provide information and/or accommodation pertaining to this job posting and/or the recruitment process in an accessible manner upon request.

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