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.

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.

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.

Brad Kusz
Property Manager

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.

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

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