Children's Ski Program Supervisor

Children's Ski Program Supervisor (Powder Pups) - Seasonal Role

Location: Chestnut Mountain Resort, Galena, IL

Position: Program Supervisor – Children's Ski Program (Powder Pups)

Schedule: Seasonal (Winter): Friday, Saturday, and Sunday (plus select holidays)

Compensation: Hourly wage (TBD) + Season pass + employee housing

About Chestnut Mountain Resort

Chestnut Mountain Resort is the Midwest's premier year-round destination, offering action-packed activities and family-friendly amenities. Our property features 60 acres of lift-accessible terrain for skiing and snowboarding, the Farside Terrain Park, Farside Downhill Mountain Bike Park, Alpine Slide, Soaring Eagle Zipline, Mississippi River Cruises, Disc Golf, Mini Golf and much more.

Our mission is to deliver memorable experiences, enhance people's lives, and create a fun, inspiring culture. We aim to create exceptional guest experiences at every touchpoint, and our employees play a key role in making that happen. We seek natural communicators, problem solvers, and enthusiastic individuals who share a passion for mountain life and providing "best day ever" experiences for every guest.

About the Powder Pups Program

Powder Pups introduces children to the joy of skiing – helping them build skills, confidence, and a lifelong love of the sport in a safe, friendly, and fun environment.

As the Program Supervisor, you'll be the heart of our winter kids' programming, ensuring that each child's first experience on the mountain is positive, exciting, and unforgettable.

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Season Details

● Program runs approximately December through March (exact dates TBD)

● Supervisor role begins with pre-season setup and instructor training

● Powder Pups operates Friday-Sunday and on select holiday weekdays

● Hourly pay reflects the seasonal,part-time nature of the position

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Role Summary

The Powder Pups Program Supervisor serves as a professional representative of Chestnut Mountain Resort, managing and leading a children's learn-to-ski program integrated with the Chestnut Ski and Snowboard School. This role requires a passionate leader dedicated to creating a positive, safe, and encouraging learning environment for young skiers.

You'll work closely with children, parents, instructors, and resort staff to deliver exceptional guest service and help each child discover the thrill of skiing.

Essential Duties & Responsibilities

• Design and lead ski lessons and activities for children ages 4-10, grouped by age and ability
• Manage enrollment, rental setup, and daily program logistics
• Act as the main point of contact for parents – build trust, communicate progress, and address questions or concerns
• Supervise and mentor a small team of instructors, fostering teamwork and collaboration across the Snowsports Department
• Create a warm, encouraging atmosphere where beginners feel safe and excited to learn
• Coordinate lesson schedules, equipment check-in/out, and parent communications
• Oversee on-hill safety, gear fitting, and smooth transitions between activities.
• Prioritize safety and uphold skier/snowboarder responsibility at all times
• Continuously improve personal skiing/riding skills and teaching skills
• Serve as a positive public ambassador for Chestnut Mountain, on and off the slopes
• Comply with Chestnut Mountain Resort's Employee Handbook and follow all resort policies regarding grooming, dress and professional conduct
• Seek opportunities to enhance the guest experience and department operations

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Safety Responsibilities

• Prioritize the safety of self, co-workers, and guests at all times
• Immediately report accidents, incidents, or unsafe conditions to the appropriate supervisor or department
• Operate all equipment safely and responsibly
• Follow all company and departmental safety policies and procedures
• Drive in compliance with all laws and Chestnut Mountain policies

Qualifications

• Must be 21 years or older
• High school diploma or equivalent required; college education preferred
• Strong skiing ability (PSIA certification preferred but not required)
• Genuine passion for skiing and working with children.
• Comfortable skiing on green runs and leading groups of young skiers
• Experience teaching, coaching, or supervising children (ages 4-10 preferred)
• Excellent communication and interpersonal skills
• Patient, creative, and energetic with a playful approach to learning
• Adaptable and eager to learn and grow professionally
• Willingness to work long and irregular hours, including weekends and holidays
• Positive, team-oriented, and professional attitude

Perks & Benefits

● Free season pass for yourself

● Employee housing available

● Supportive, fun, and collaborative team environment

● Instructor training and skill development opportunities

● Endless hot chocolate and smiles from your students

● The joy of helping a child take their first turns and fall in love with skiing

★ Join Us

If you're ready to share your love of skiing and create unforgettable winter memories for young adventurers, we'd love to have you on the Chestnut Mountain t