About BBBSW and the Position

Big Brothers Big Sisters of Winnipeg has been providing life-changing mentoring relationships to children and youth for over 55 years. As we expand our programs, deepen community partnerships, and innovate new ways to support young people, we are seeking a Mentoring Specialist to deliver high-quality, relationship-focused programming across multiple mentoring streams.

This role is ideal for someone who is joyful, curious, highly organized, and passionate about youth development. You will work directly with volunteers, caregivers, and youth to create, support, and sustain healthy mentoring relationships that help young people thrive. An ideal candidate is someone who brings warmth, curiosity, and professionalism to every interaction. Who thrives in environments where relationship-building and strength-based support are the anchors to our work.

Position Overview & Key Responsibilities

Deliver High-Quality Mentoring Programs

- Facilitate all aspects of match creation, including interviewing youth and volunteers, conducting assessments, and preparing families for program participation.
- Lead match introductions and support new matches as they begin their mentoring journey both in Community and in School Settings
- Provide ongoing coaching, guidance, and monitoring to established matches according to National Child Safety Standards.
- Support group mentoring programs, including supervision, facilitation, and behaviour management.

Casework, Documentation & Standards
- Maintain accurate, timely case notes and documentation
- Experience with computers, Word, Outlook Microsoft Dynamics/CRM, Sharepoint, TEAMS required
- Organization managing multiple needs
- Conduct match closures, including meetings and follow-up communication.
- Prepare reports, statistics,



and written content for internal and external use (board reports, newsletters, awards, etc.).

Relationship Building & Family Support
- Interact joyfully and respectfully with people of all ages and cultural backgrounds.
- Communicate effectively by phone, email, text, in-home, and in schools.
- Support families through strengths-based, anti-oppressive, and culturally aware practice.
- Make referrals to community agencies when appropriate.

Training, Events & Community Engagement
- Deliver pre-match training for volunteers, youth, and caregivers.
- Provide program-specific training as required.
- Participate in agency events related to recruitment, fundraising, and recreation.
- Coordinate special opportunities for youth and volunteers (e.g., camperships, scholarships, special programs).

Qualifications
- A 2-year diploma or degree in Human Services, Social Work, Sociology, Psychology, Human Ecology, Conflict Resolution, or a related field.
- Candidates in their final year of study or those with extensive relevant experience may also be considered.
- Solid interviewing, assessment, coaching, and group facilitation skills.
- Excellent written and verbal communication skills — you enjoy writing and dialogue.
- Ability to see people in context and understand issues from multiple perspectives.
- Comfort working independently, managing time well, and adapting to changing needs.
- High proficiency with technology:



CRM/SDP systems, Outlook, TEAMS, SharePoint.
- Valid driver’s license and access to a smartphone.

Additional Skills/Experience
- Conflict resolution skills
- Volunteer management experience
- Leadership and time management
- Understanding of mentorship and youth development
- Ability to work flexible hours (afternoons/evenings + occasional weekends)

Schedule & Work Environment
- 35 hours/week
- Anticipated start date to be negotiated, with hopes of starting before October. This is a term position until May 19, 2027
- Primarily afternoons and evenings (ex. 11-6 PM or 1-8 PM)
- 1–2 weekend shifts per month (ex. g., 12- 4 PM)
- This position is front-line and expected to meet with clients/volunteers/school and community liaisons daily
- Occasional work-from-home flexibility, to be approved by supervisor

Why Join Us? At Big Brothers Big Sisters of Winnipeg, you will be part of a team committed to justice, equity, diversity, and inclusion. We value lived experience and encourage applicants from equity-seeking groups to self-identify. You will have the opportunity to make a meaningful impact on youth, families, and volunteers across Winnipeg.

Requirements

- Cover Letter and Resume outlining specific experience to the job posting
- Three work or volunteer references
- Successful candidates will be required to complete a Child Abuse Registry Check
- Police Record Check with Vulnerable Sector Check
- Copy of Diploma (if graduated)

Pay: From $40,000.00 per year

Benefits

- Casual dress
- Flexible schedule
- On-site parking

Application question(s):
- Do you have experience managing a caseload?
- Do you have experience working with children, caregivers, or mentors?

Work Location: In person

📌 Mentoring Specialist (Winnipeg)
🏢 Big Brothers Big Sisters
📍 Winnipeg