Accessible Employer: YesOpen to International applicants with valid Canadian Work permits: YesCypress Mountain is seeking an experienced and passionate Senior Supervisor to join our Snow Sports School leadership team for the 2026/27 winter season. This role is ideal for an experienced snowsports professional who is passionate about instructor development, operational leadership, program coordination, and delivering exceptional guest experiences in a dynamic mountain environment.The Senior Supervisor is responsible for the planning, coordination, implementation, and oversight of Snow Sports School programs and instructional teams within assigned operational areas. The role supports team members development, training initiatives, program delivery, guest experience standards, safety compliance, and operational excellence across medium to large-scale lesson products.The Senior Supervisor works closely with Directors, Managers, Supervisors, and Coordinators to support the growth and development of instructors and supervisors while ensuring daily operations run efficiently, professionally, and safely.Responsibilities & QualificationsProgram Coordination & Operational LeadershipCoordinate and oversee daily Snow Sport School operations within assigned program areas.Support the planning, scheduling, and implementation of lesson products, seasonal programs, and training initiatives.Assist with operational planning, team coordination, and resource allocation to support business needs.Monitor daily program flow and provide operational support to Supervisors and Instructor teams.Utilize scheduling and operational systems including Flaik and RTP to coordinate lessons, instructors, and program logistics.Ensure Snow School programs are delivered in accordance with company standards, policies, and procedures.Collaborate with leadership teams to support long-term operational growth and program development.Team Leadership, Training and DevelopmentLead, mentor, and support Supervisors, Lead Instructors, and Snow Sports Instructors within assigned areas.Coordinate onboarding and orientation support for new Instructors and Supervisors.Deliver coaching, technical feedback, and professional development training in skiing and snowboarding instruction.Support team performance management through regular feedback, mentoring, and leadership development.Assist in creating a positive workplace culture focused on professionalism, teamwork,



communication, and continuous improvement.Lead one day per week of community engagement, team wellness, training, or Instructor development initiatives based on operational needs and areas of expertise.Guest Experience & CommunicationSupport the delivery of exceptional guest service standards across all Snow Sports School operations.Act as an escalation point for guest concerns, questions, and feedback within assigned program areas.Work collaboratively with Guest Services, Rentals, Food & Beverage, Patrol, and other departments to support the overall guest experience.Communicate operational updates and program information clearly with team, guests, and leadership teams.Assist in implementing service improvement initiatives and maintaining high guest satisfaction standards.Safety & Risk ManagementPromote and uphold all safety policies, procedures, and training standards within Snow Sports School operations.Actively uphold the Alpine Responsibility Code, Duty of Care, Emergency Response Procedures and all applicable Safe Work Procedures.Support incident response, documentation, reporting, and follow-up procedures.Ensure incident, hazard, and near‑miss documentation is completed accurately and promptly.Assist in creating a safe, respectful, and inclusive environment for guests and employees.Core ValuesK.R.P. – Kindness, Respect, and Professionalism.L.E.A.D.S. – Long‑Term Thinking, Excellence in Execution, Attitude is Everything, Develop Great People and Serve First.Qualifications / CompetenciesExtensive skiing and/or snowboarding instructional experience.Ability to coordinate team schedules, operational logistics, and program delivery.Solid leadership, mentoring, and conflict‑resolution skills.Knowledge of Flaik, RTP, or similar scheduling and operational systems considered an asset.Ability to work in a fast‑paced outdoor environment.Professional, reliable, punctual, and safety‑minded.Excellent communication and interpersonal skills with peers,



guests and subordinates.Strong organization and planning skills with the ability to coordinate people and resources efficiently.Trustworthy & dependable: able to work independently and collaboratively.Ability to solve problems and thrive in a fast‑paced, dynamic environment.Openness to feedback & willingness to grow.Ability to ski or snowboard for extended periods in variable weather conditions.Ability to lift, carry, and maneuver equipment as required.Comfortable working outdoors in cold, snowy, rainy and changing alpine environments.Ability to stand, walk, kneel, and assist guests on uneven terrain.Certificates, Licenses, RegistrationsMinimum CSIA / PSIC / CASI Level 3 certification (or recognized foreign equivalent) and in good standing within certifying organization.Relevant post‑secondary education in Sports Science, Recreation Management, Education, Leadership, or a related field preferred.Minimum 5 years of supervisory, leadership, or program coordination experience within a Snow School or recreation environment.Minimum of 16 years of age or older at the time of hire. *To meet BCESA and ability to work alone while supervising others in an alpine workplace.A transparent Criminal Record check dated April 2025 or later is required.Must be able to legally work in Canada.Availability & Seasonal CommitmentMid‑November – mid‑April (weather and business‑volume dependent).Availability during Winter Holidays is a requirement of employment.Onboarding & OrientationAttend a minimum of two 6 hour in‑person training and orientation seminars (or acceptable alternative) held at Cypress Mountain Snow School in late November and/or early December.Complete all online training and submit required work, including eligibility documents prior to first day of work.27.50-28.50Other Perks / BenefitsUnlimited all mountain access to skiing, snowboarding, cross‑country, snowshoeing, and snow tubing.Free lessons for staff.Team member discounts in rentals, retail, and F&B outlets.Skiing/riding perks at sister resorts and other reciprocal mountains.Team events and social activities all season long.Hands‑on learning opportunities to grow your career.Work on the biggest local mountain.Ride the best snow & terrain.Be part of a unique mountaintop workplace creating life‑long memories.Job Application Processhttps://www.Cypressmountain.Com/employment#J-18808-Ljbffr

📌 Snow Sports School – Senior Supervisor - C$27.5 - C$28.5 An Hour (Winnipeg)
🏢 Cypress Mountain
📍 Winnipeg