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Supervisor - Outland Youth Program; Summer Field Placement

Job in Winnipeg, Manitoba, A3C, Canada
Listing for: Dexterra
Seasonal/Temporary, Contract position
Listed on 2026-03-01
Job specializations:
  • Management
    Operations Manager, Program / Project Manager
Salary/Wage Range or Industry Benchmark: 30000 - 60000 CAD Yearly CAD 30000.00 60000.00 YEAR
Job Description & How to Apply Below
Position: Supervisor - Outland Youth Employment Program (2026 Summer Contract, 7 Weeks, Field Placement)

Supervisor - Outland Youth Employment Program (2026 Summer Contract, 7 Weeks, Field Placement)

  • Contract
WHO ARE WE?

The Outland Youth Employment Program is a national network of innovative education, training and work opportunities for Indigenous youth that includes our award winning six-week work integrated learning summer program.

Every position involves elements of personal and organizational development and maintenance. We aim to foster a workplace that is safe, fun, flexible, transparent, inclusive, and supportive. As staff, we work collaboratively alongside youth, communities and partners to continually live out our mission.

There’s no real typical day  work hard to be nimble and adaptable to the changing needs of the youth and partners we work with. If you’re looking for a fast paced, multifaceted, energizing and rewarding work environment that will challenge you, then we want to hear from you!

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WHAT'S THE JOB?

This position takes place onsite outside of Swan River, MB. Vehicle provided.

OYEP Supervisors are responsible for the supervision, safety, and overall well-being of youth and staff for the duration of the program. Supervisors maintain a clean, orderly, and professional presentation of camp and operations at all times. This is a live-in leadership role overseeing one full cohort at the site level for the summer program. Program delivery occurs in a remote, land-based setting with rustic cabin-style accommodations and shared facilities, requiring adaptability, maturity, and comfort in a communal living environment.

Supervisors are required to provide consistent, supportive supervision and guidance to staff and participants, assisting with questions, problem-solving, and situations that may arise. Specifically, Supervisors must maintain a safe, structured, and predictable environment for all aspects of camp operations; ensure clarity and adherence to the program schedule; provide final judgment on disciplinary situations; and ensure all staff and participants understand their roles, responsibilities, and behavioral expectations.

Supervisors are also responsible for supporting youth development by coaching participants through workplace expectations, conflict resolution, and personal growth opportunities. Many Rangers are experiencing their first job and first paycheque;
Supervisors play a key role in modeling professionalism, accountability, and workplace readiness.

In addition, Supervisors must serve as a positive, professional, and productive role model for youth at all times.

Supervisors are expected to uphold and support culturally respectful practices at site, working alongside community partners, Elders, and Knowledge Keepers where applicable. This includes supporting culturally grounded activities and ceremonies as guided by community leadership.

Supervisors will work directly with the Operation's Manager to achieve safety and quality programming throughout the summer.

Your work will include, but is not limited to:
  • Provide active oversight and assistance in all work projects and classroom sessions to ensure safety, productivity, and learning objectives are met
  • Maintain and enforce Outland’s workplace health and safety regulations and emergency response procedures
  • Report near misses, hazards, and safety incidents in a timely manner
  • Lead incident management and support emergency response as required
  • Monitor staff and Rangers’ safe operating procedures and PPE compliance
Vehicle & Equipment Safety
  • Ensure safe operation, supervision, and oversight of all program vehicles, boats, tools, and equipment
  • Maintain awareness of vehicle and equipment maintenance requirements and report deficiencies promptly
  • Ensure pre-use inspections are completed and documented as required
  • Promote and model safe driving practices and responsible equipment use at all times
Education & Certification Oversight
  • Ensure delivery of industry certifications and support education components, including high school credit requirements where applicable
Healthy Living & Camp Culture
  • Promote and model healthy living behaviors, including:
    • Healthy lifestyle choices
    • Active living
    • Positive social interaction and cohesive group living
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