Manager of Site-Based & Group Programming

Big Brothers Big Sisters of Winnipeg - Full-Time Contract Flex Hours Required (35 hrs/week; evenings and weekends depending on program schedule) Annual Salary: $50,000 Term: 12 Months (potential to extend based on funding) Location: Winnipeg, MB In Office or Partner Sites

Our Mission

For 55 years, Big Brothers Big Sisters of Winnipeg has empowered youth through mentorship and meaningful relationships. As we grow and adapt, our commitment to inclusive and innovative programming continues to light the way.

We value diversity and welcome applicants from all backgrounds, particularly those who reflect the communities we serve. Your lived experience matters. Your voice matters.

About the Role

This position is ideal for someone that loves interacting with people and helping folks build growth mindsets, positive self esteem and acceptance for youth in mentoring relationships. This position is a cup filler for folks that enjoy playing while on the job. Utilizing creativity, engagement and joy while attuning to different audiences and strengths and needs.

As our Manager of Site-Based Programming, you'll be responsible for +4 part-time staff within our site-based programs, including our activity centre and our school-based programs, while also having a caseload. You will build and nurture relationships with Winnipeg Schools, where we provide group mentoring for teen mentors with mentees at adjacent elementary schools(Youth In School Mentoring (YISM), currently supporting 5 high schools; 5 elementary schools but looking to expand; 1:1 In School Mentoring programming, our Community Service Learning programming (Monthly group with University Mentors), Ukulele group, and other site based programming designed based on response to community and waitlist needs.

You'll bring curiosity, empathy, and a systems-aware mindset. We love a good multitasker with excellent communication, tech-savvy comfort, and a joyful spirit; time management and organization are integral to this role. You will guide mentor-mentee matches across our programs, build strong connections with the community, and nurture youth development through trauma-informed and anti-oppressive approaches. This is the frontline of mentorship-where impactful relationships are made and grown.

Key Responsibilities

Interview, assess, and match youth and mentors
Provide training, coaching, and supervision of mentoring relationships
Maintain data within Microsoft Dynamics
Facilitate and design responsive group trainings and mentor check-ins
Ensure Standards of Big Brothers Big Sisters of Canada programming Quality Assurance are met to support safe and effective mentoring.
Support families in navigating systems and resources with a strength-based and youth focused approach
Coordinate with all staff and volunteers for successful program delivery
Promote positive youth development and community engagement

Mandatory Requirements

Completion of a 2-year diploma or degree in social work, human services, psychology, or a related field
Valid Manitoba Class 5F Driver's Licence and access to a reliable vehicle
Smartphone capable of supporting work-related applications
Strong proficiency with Microsoft 365 (Word, Excel, Outlook, etc.)
Clear Criminal Record + Vulnerable Sector Search
Clear Child Abuse Registry Check
Legal entitlement to work in Canada

Essential Qualifications

Background in social service delivery, anti-oppression work, and case management
Experience with child development, conflict resolution, and mentorship theories
Capacity to work afternoon, evening, and weekend hours
Ability to build rapport across cultures, ages, and identities
Exceptional written and verbal communication
Joyful, curious, and adaptable approach to facilitation and documentation
Strong organizational and interpersonal skills

Applicant Experience (please demonstrate you have had the following experience in your cover letter):

Required: Applicant must have experience hosting group programming
Required: Applicant must have experience managing staff
Required: Applicant must have experience, education or training regarding working with 2SLGBTQIA+ youth and other diverse communities
Required: Applicant must have experience conducting interviews/assessments
Required: Applicant must have experience working with volunteers, youth, and families
Required: Applicant must have an awareness of child safety practices
Required: Applicant has experience facilitating dynamic trainings to different audiences
Preferred: Applicant has experience working within a school or with various community stakeholders

Benefits & Flexibility

Flexible work hours; primary range 10-8 and 1-2 weekend shifts a month; 35 hours a week;
Negotiable opportunities to work from home on occasion
Casual dress and on-site parking
Benefits available upon renewal to permanent
Opportunity to create lasting change in youth lives

Application Details

Deadline: August 15, 2025
Estimated Start Date: TBD; September 2025
To Apply: Send your resume and cover letter to
Learn More:

Job Types: Full-time, Fixed term contract
Contract length: 12 months

Pay: $50,000.00 per year

Benefits:
Casual dress
Flexible schedule
On-site parking
Paid time off
Schedule:
Day shift
Evening shift
Monday to Friday
Weekends as needed

Education:
Bachelor's Degree (required)

Experience:
Leadership: 2 years (required)

Work Location: In person

Application deadline: 2025-08-15