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. 

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

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

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