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Wilderness Inquiry

  • 33095 Little Sand Bay Rd, Bayfield, Wisconsin
  • https://www.wildernessinquiry.org/

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Little Sand Bay Sea Kayak Outdoor Leader


min experience

salary range

$112 - $160 / day

Additional Job Details

International Applicants Allowed?
Work Visa Sponsoring Available

Job Overview


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 togetherseeking the exceptional, and finding a way.

Outdoor Leaders create the magic at WI, creating life changing outdoor experiences for individuals and families of all backgrounds and abilities. Our Little Sand Bay Sea Kayak staff lead 1-5 day, front and/or backcountry kayaking adventures in the Apostle Islands out of our Little Sand Bay Base Camp near Bayfield, Wisconsin. Some staff choose to live at the base camp during the season, and others will be based out of Minneapolis and commute for each trip. Lodging at Little Sand Bay is free for Outdoor Leaders.

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 this position.


  • May 19th – June 3rd, 2022: Required Training (see schedule in TRAINING section below)
  • June through September – Main programming season in the Apostle Islands
  • September through mid to late October – options for local day programming in the twin cities area as well as work on National Canoemobile Tours


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 wellbeing 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 needs including evacuations.
  • Care for equipment while in the backcountry and at base camp.
  • Proficiently perform activities conducted on WI trips including navigating routes in the front and backcountry, cooking, kayaking, hiking, camping, etc.
  • Safely drive a 15-passenger van pulling a loaded trailer in all weather and road conditions (contingent upon driver eligibility).

Pre-Trip Prep & Post-Trip Paperwork 

  • Work with logistical staff to pack-in and pack-out gear and food.
  • Complete post trip paperwork including evaluations, incident reports and trip summaries.


Required certifications (or ability to obtain- Wilderness Inquiry frequently sponsors courses before seasonal training):

  • A minimum of Basic First Aid & CPR required. Wilderness First Aid (WFA) or Wilderness First Responder (WFR) preferred (staff must possess a WFA or WFR to be eligible for promotion in kayak leadership)
  • Wilderness Water Safety or Lifeguard/Professional Rescuer

Preferred Certifications: 

  • ACA Level 2: Essentials of Kayak Touring Skills Assessment, or ACA Level 3: Coastal Kayak Trip Leader
  • *Current Driver’s License and a safe driving record dating back at least five years

*Driver’s license status will not impact eligibility for hire, but may impact eligibility to work specific trips

For information on how to obtain certifications visit click this link.

TRAINING: Required and hosted by Wilderness Inquiry

  • May 19th – 24th, 2022 – Kayak skills training (staff can choose to participate in an optional ACA Level 2 certification upon completion of this training. Fees for kayak training are covered by WI, however certification fees are the responsibility of the staff member).
  • May 25th – 27th, 2022 – All staff Wilderness Inquiry overview training
  • May 31st – June 3rd, 2022- All staff Wilderness Inquiry field training

Qualified applicants may be asked to participate in WI Driver Training and Voyageur Canoe Stern Training & Assessment, if applicable. All new Outdoor Leader hires are contingent upon successful completion of required training.


Outdoor Leaders are classified according to skill and experience and compensated on a per event basis starting at $112/day. Further details on compensation are available upon request. Opportunities for advancement available upon demonstrated performance with Wilderness Inquiry. Staff housing and professional service stipends available.

All WI Outdoor Leaders regardless of experience are compensated at $14/hr and/or $112/day for training.

Minimum Requirements

  • 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.
  • Must pass a background check.
  • Complete COVID-19 vaccines are mandated for all WI staff and interns
  • The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
    • While performing the duties of this position, the employee is frequently required to sit; talk or hear; and use hands to handle, or touch objects or controls.
    • The employee is regularly required to stand and walk.
    • On a regular occasion the employee may be required to stoop, bend or reach above the shoulders.
    • Must be able to lift and carry heavy loads up to 50lbs over rough terrain for distances of up to 1,000 feet.
    • To meet the demands of the job, the employee must be able to make loud verbal commands, sit and stand for significant periods of time while also directing vessels such as a canoe, use vision to directionally navigate safely, and endure a wide variety of temperatures and elements.
    • Specific vision abilities required by this job include close vision, distance vision, peripheral vision, depth perception, and ability to adjust focus.

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