Current Job Openings

Retail and Social Media Manager

WinMan Trails is looking for a Retail and Social Media Manager to bring energy, creativity, and expertise to our team.

Details:

  • Position Term (Flexible) – May to October 2025
  • Weekly Hours – 35-40 Hours per week
  • Compensation: $16 - $20 per hour
  • Application Deadline: rolling until position is filled
  • Must be able to work weekends

Assistant Trail Builder

Working under WinMan’s two professional Trail Builders, the Assistant Trail Builder will be responsible for construction, maintenance, and enhancement of our mountain bike, hiking and skiing trail systems.

Details:

  • Position Term (Flexible) – May to October 2025
  • Weekly Hours – 40 Hours per week
  • Compensation: $17 - $20 per hour
  • Application Deadline: rolling until position is filled

To apply, please email your resume and letter of interest to Isaac at info@winmantrails.com

Meet the Team

WinMan Trails employees 5 full-time staff who manage, build and maintain our year-round trail system.

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Isaac Cowart

Executive Director

Isaac joined the WinMan Crew in April 2022. Prior to that, he served as a clinic director for several organizations and successfully managed clinic operations through multiple acquisitions and leadership transitions. He brings 20+ years of mountain biking experience along with professional credentials as a Certified Run Coach, Certified Mountain Bike Instructor, and BikeFit Specialist. His business and operations experience, combined with his passion for fitness and the outdoors, makes WinMan Trails the perfect fit. 

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Sam Wolter

Director of Community Engagement

Sam brings an immense amount of knowledge and talent that will allow our year-round, 4-season trail system to continue to grow and evolve well into the future. With a degree in tourism management and years of experience in the non-profit field, her diverse background will allow WinMan to be an even stronger resource and asset for our community. Sam recently served as the marketing, membership, and development coordinator at North Lakeland Discovery Center before joining the team at WinMan in March 2024.

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Brad Kusz

Property Manager

Brad Kusz has served as the property manager of WinMan Trails since the Spring of 2019. His depth and breadth of knowledge as a tradesman has allowed WinMan to bring many projects and building plans in-house, saving both time and money. He has worked as a carpenter, plumber, and an electrician as well as in engine and auto body repair. Furthermore, he has been in the ski and bike industry for more than 30 years and brings not only technical skills as a bike mechanic but knowledge and experience of customers and trail users.

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Jeremy Johnson

Trail Builder, Mechanic, Groomer

Jeremy worked as a professional trail builder for Flow Track constructing mountain bike trails throughout the upper Midwest including at WinMan. His experience as a trail builder, welder, mechanic and machine operator allows him to share his talents and continue to grow and improve our year round trail system.

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Joel Kleimola

Lead Trail Builder and Groomer

Joel was trained as a mountain bike trail builder by the nation's largest and most respected trail building contractor, Rock Solid. His vision and creative eye transforms normal terrain into trails that excite and will endure the test of time. His expertise brings a level of commitment to maintaining a high-quality trail system that meets the needs of all our users. 

Part-Time Staff

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Vanessa Embling

Bar and Apparel Shop

If you ever visit the Bar and Apparel Shop you know Vanessa (and probably Archie too). Her smiling face and helpful advice makes sure you have a great day at WinMan. Little known fact, she is also a professional photographer and many of the amazing pictures you see on our social media accounts or the website are thanks to her.

Board of Directors

Sean McCaleb

President

Diane Linn

Member

Amy Kobussen

Board Liaison

Rick Gering

Vice President

Mike Bartling

Member

Isaac Cowart

Secretary/Treasurer

Catherine Egelhoff

Member

Brad Kusz

Member

Paul Egelhoff

Member