At Wilderness Inquiry, we believe that everyone belongs. We work to ensure this belief holds true in our workplace, in our community, and in the outdoors. We pursue this belief through our mission and shared values of paddling together, seeking the exceptional, and finding a way.
Outdoor Leaders create the magic at WI, creating life changing outdoor experiences for adults, youth, and families of all backgrounds and abilities. They facilitate and execute programming in a variety of locations and settings.

For the 2021 summer season, we are currently hiring for two distinct Outdoor Leader Positions:

Little Sand Bay Sea Kayak Outdoor Leader: Our Apostle Islands kayaking staff lead 3-5 day, front and/or backcountry kayaking and hiking adventures out of our Little Sand Bay Base Camp near Bayfield, Wisconsin.

Backcountry Outdoor Leader: Our extended trip team of Outdoor Leaders predominantly lead 3-5 day trips in the Boundary Waters Canoe Area, Voyageurs National Park, Superior Hiking Trail, and the St. Croix and Namekagon rivers in Wisconsin.

To apply for and review full job descriptions for each individual position please click here: https://www.wildernessinquiry.org/about-wilderness-inquiry_old/employment-volunteers/employment-opportunities/

We recognize that as an industry, there is much to do to increase representation in our field to reflect the communities we aim to serve. We also know that diversity of identities, experiences and ways of thinking result in better solutions for our communities. For this reason, we especially encourage applicants from communities who experience systemic barriers – including people of color, women, LGBTQIA+ and people with disabilities – to apply for these positions.

The primary responsibility of Outdoor Leaders is to serve participants and ensure the safety, quality and cost-effectiveness of WI experiences. Outdoor Leaders are responsible for the lives and well being of WI participants throughout a WI adventure. Life as a WI Outdoor Leader can be fun, exciting, and incredibly rewarding, but it is also a tremendous amount of responsibility and it can involve a lot of hard and challenging work.

Group Facilitation
• Provide excellent leadership for adults and families.
• Use effective judgment and decision making regarding trip implementation.
• Uphold Wilderness Inquiry’s Trail Community Agreements

On-Trail Technical Skills & Safety
• Assess participant ability and expectations to safely and effectively meet their needs.
• Provide emergency first aid and conduct and/or assist in back-country medical issues including evacuations.
• Care for equipment while in the field.
• Proficiently perform activities conducted on WI trips including navigating routes in the front and backcountry, cooking, canoeing, hiking, camping, etc.
• Safely drive a 15-passenger van pulling a loaded trailer in all weather and road conditions.

Tagged as: Backcountry Skills, Instruction and Guiding


The ability to plan, implement and follow through with responsibilities is essential. Must have an aptitude for wilderness leadership, excellent people skills, the ability to oversee projects independently and as part of a team, and strong communication skills. Must be interested in leading extended wilderness trips for people of all abilities, including people with disabilities. Must be willing to keep flexible hours.

Required Skills:

Required certifications, or ability to obtain (courses may be offered as an addition to initial training):
Basic First Aid & CPR required, Wilderness First Aid (WFA), Wilderness First Responder (WFR), or higher preferred (A minimum of WFA required for SeaKayak Outdoor Leaders)
Wilderness Water Safety or Lifeguard/Professional Rescuer
Current Driver's License and a safe driving record dating back at least 5 years

About Wilderness Inquiry

Wilderness Inquiry’s mission is to connect people from all walks of life to the natural world through shared outdoor adventures. Through the medium of outdoor adventure travel, we inspire personal growth, enhanced awareness of the environment and community integration. Wilderness Inquiry is all about access, inclusion, and opportunity. We believe exploration of the natural world is a birthright we all share, and we act on that belief. We operate in a manner that facilitates full participation by everyone, including people of all ages, background, and abilities.

Application Instructions

Please apply on our website using this link: https://www.wildernessinquiry.org/about-wilderness-inquiry_old/employment-volunteers/employment-opportunities/