Job Description

Competition #2026-240-CPCareer Success Coach (2026-240-CP)Employment Type:Contract Hourly, until September 30, 2026 Bargaining Unit (1 Vacancy)Work Hours:35 hours/week (9:00am-5:00pm)Work Setting:Exclusively Onsite (219 Dufferin Street, Toronto, ON)Salary:G: $31.85/hrApplication Deadline:June 1, 2026 by 11:59 pmWho We Are
WoodGreen is a team of diverse and innovative change makers working together to make a difference in our communities. A United Way Anchor Agency with a proven track record and an entrepreneurial mindset, we continuously seek to develop solutions to critical social needs while striving to become a Centre for Equity.
Visit www.woodgreen.org to learn more about who we are and to review our Equity Statement
We are committed to building an inclusive and diverse workforce, representative of the communities we serve. We encourage, and are pleased to consider, applications from Indigenous peoples, racialized persons/persons of colour, women/women identifying, persons with disabilities, 2SLGBTQIA+ persons, and others who contribute towards promoting innovative ideas and solutions.

Program Overview – Integrated Employment Services, Community Programs
The Career Success Coach is the trusted support resource for clients who have entered employment, as well as a touchstone to WoodGreen for all other clients regardless of outcome for the first 12 months after pre-employment ends. They carry a caseload of clients and connect with each on a monthly basis to understand their employment status, offer support and help remove barriers to their success. The Career Success Coach, Integrated Employment Services, is part of a high-performance team that improves communities, families and individual lives through effective access to employment. Working at a local Integrated Employment Services Centre or other sites in the City of Toronto, they ensure that clients and employers are supported after employment starts and that required documentation is obtained as part of WoodGreen performance-based funding agreement.

What You Will Do

• Build rapport and an emotionally supportive context for each client to feel trusting, engage readily in the job search process, and believe in their own success to obtain employment. Help clients build their motivation and confidence.
• Ensure clients understand the Integrated Employment Services approach and the value of services provided, particularly retention support.
• Create equity in all aspects of service delivery, striving for inclusion and equitable outcomes for all jobseekers who come to WoodGreen.
• At the start of employment for each client, responsible for administrating the Transition & Retention Checklist (TRC) with clients who start employment (required for a Brokered Incentive Agreement (BIA) and must be attempted for all).
• Accountable for conducting on-time monitoring checkpoints at one, three, six and twelve months. Monitoring involves direct contact with the client and completion of the Employment Status Questionnaire (ESQ), which pertains to employment status, hours worked, wage, occupation, and client experience.
• Manage a caseload of clients: Using excellent time management, standardized regular communications, effective appointment planning, and interventions when necessary, help clients remain in employment throughout the first year after obtaining a job.
• Enter case notes and data in CaMS and/or WCG’s CRM as required.
• Deliver retention support that is flexible and becomes less or more intensive based on the results of the TRC and the ongoing situation.
• Participate in the client care team with the Employment Consultant and Job Developer (if involved), meeting clients during the early stages and helping sell clients on the process and value of in-work support.
• Prepare monthly forecasts with the risk status of clients in caseload, indicating those at higher risk to fall out of work.
• Liaise between the client and/or employer to assess job satisfaction, identify potential performance or workplace issues (e.g., absenteeism, behavioral concerns, task completion, work schedule, or workplace/cultural integration), and assist in resolving them.
• As needed, sit with and support clients as they use onsite computers while they engage in activities that help return them to work or access life stabilization supports.
• Readily participate in training and coaching to support achievement of targets. Use supervisor monitors and feedback as a constructive learning experience.
• Demonstrate excellent customer service and skills in interactions with employers and clients.
• In an efficient and prompt manner, complete all documentation and data entry per WoodGreen standard operating procedures (e.g. client notes, data entry, referrals, updating forms).
• Develop and/or learn to facilitate existing materials and deliver in group activities or workshops, particularly on topics related to job retention, both in person and online, as part of a regular rotation of duties within the team.
• Participate in and complete upgrading training and education as required by WoodGreen.
• Participate in regular supervisory sessions with the manager, as well as regular staff and unit meetings within the unit.
• Perform other duties as assigned.

What You Bring to the Team

• Degree or diploma in Social Work, Social Services Worker, Business, Human Resources, Community Development or related field
• Strong clerical aptitude, including attention to detail, organizational skills, data management, documentation accuracy, and efficient multitasking.
• Strong computer literacy, including Microsoft Office suite and database application, online learning, online job search, online research, building an online presence (e.g. with LinkedIn), networking and community building online.
• Experience and/or training in career counselling (e.g. needs assessment, job search, job development, job retention)
• Excellent customer service skills
• Experience in leading group workshops or activities
• Highly ethical, compassionate and purpose driven with an overarching desire to support client success toward employment success.
• Energy and enthusiasm to meet new people, listen and learn about their needs and experience, and work to improve their life and the lives and their families.
• Oriented toward coaching and facilitating others to share information and suggest success strategies;
• Comfortable speaking with employers to understand their needs/perspective while advocating for clients.

What Will Set You Apart

• A strong sense of personal accountability for achieving individual targets
• Coachable and able to adapt and change in procedures, systems, client needs, external trends, etc. as the service delivery context evolves.
• Patience, compassion and sensitivity to deal with different cultures and different levels of abilities among clients, colleagues, partners and others in the work environment.
• Understanding of and ability to communicate principles and practice of diversity and anti-racism.
• Excellent interpersonal skills as well as verbal and written communication skills.
• Primarily working in-person at a WoodGreen location. Ability to work a staggered schedule that could include up to two evenings (e.g. 6 p.m. to 8 p.m.) per week and occasional weekends (e.g. Saturday 9 a.m. – 11:00 a.m.) working from home to place client calls.
• Ability to report to work at various WoodGreen locations throughout Toronto.

WoodGreen is an equal opportunity employer. We are committed to providing an inclusive and barrier-free selection process and work environment. If contacted in relation to an employment opportunity, please advise our People & Culture representatives at careers@woodgreen.org of the accommodation measures required. Information received relating to accommodation will be addressed confidentially.

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