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

Job Description

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

Leadership & Staff Development

• Operate as an organized leadership team with Crew Leaders and Management-in-Training to ensure constant support in all situations
• Maintain clear and consistent communication with national management and site leadership
• Work with Management-in-Training to develop their skills and prepare them for future Crew Leader responsibilities
• Ensure staff and Rangers consistently meet behavioral, safety, and professional standards

Program Administration & Operations

• Document and reflect on daily activities and attend evening management meetings with thoughtful insights and solutions
• Complete and submit weekly reports to SharePoint
• Complete and submit daily payroll accurately and on time
• Manage weekly activity schedules and timelines to ensure smooth program delivery
• Represent OYEP professionally and maintain strong partner and industry relations at the site level

WHAT'S IN IT FOR YOU?

• Experience living out in nature!
• Ability to expand skills in a remote camp atmosphere
• Career advancement opportunities
• Zero cost of living while working on site
• Pay is combination of hourly and day rated

Qualifications

WHO ARE WE LOOKING FOR?

Applicants with backgrounds, education, or demonstrated experience in youth development, social services, education, training environments, outdoor leadership, or related fields are encouraged to apply.

Minimum 2–3 years of leadership, supervisory, or team management experience is preferred. Experience working with youth in structured, residential, outdoor, or camp environments is considered a strong asset.

Must be available to work for the full duration of the summer program (minimum 7-week live-in contract during July and August).

Strong communication, conflict resolution, and leadership skills, with the ability to exercise sound judgment and make decisions in high-pressure or dynamic situations.

Demonstrated ability to manage schedules, documentation, reporting, and administrative responsibilities effectively.

Proficiency in MS Office and administrative systems; experience with reporting platforms (e.g., SharePoint) is an asset.

Must hold a valid driver’s license in good standing and provide a clean driver’s abstract.

Experience operating trucks, trailers, or work-related equipment in a safe and responsible manner is an asset.

Current Level 1 First Aid & CPR certification is required (or willingness to obtain during the program. Wilderness or advanced first aid training is considered an asset.

Ability to live and work in a remote, land-based setting with rustic cabin-style accommodations and shared facilities for the full duration of the program.

Must be able to successfully complete a vulnerable sector check.

Additional Information

Physical Requirements

Be able to handle the following physical demands:

Lift, carry, push, or pull up to 50 lbs
Climb ladders or stairs
Stand, walk, squat, kneel, or sit according to task for extended periods
Perform repetitive hand work requiring full use of both hands
Perform work with arms extended or above shoulder height
Work outdoors in varying weather conditions

Dexterra Group is an equal opportunity employer committed to diversity and inclusion. We are pleased to consider all qualified applicants for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, protected veterans’ status, Indigenous status, or any other legally protected factors. Disability-related accommodations during the hiring selection process are available upon request.

#IND4