Field Instructor (Trip Leader, Co-Leader, Intern)

This job has been Expired
The Road Less Traveled
Job Overview

State/Location of Employing Organization: Our office is based in Chicago, but our participants and Field Instructors have the opportunity to venture to unique and culturally rich spots in the American West, California, Hawaii, Florida Keys, the Gulf Coast, Belize, Costa Rica, Ecuador, Italy, Norway, Michigan, Bonaire, New Zealand, Tanzania, Thailand, Vietnam, and Iceland

Position Qualifications: The following are characteristics/qualifications that each staff person is expected to match regardless of position:


Minimum of Bachelor’s degree or in the process of completing a degree.


Must be 21 years of age.

Current WFR or WEMT

This certification needs to be complete by the start of staff training and CURRENT through the end of employment.

Lifeguard Training or Swiftwater Rescue

These are preferred certifications but not mandatory.

Current Unrestricted Drivers License


Previous experience working with and/or teaching young people ranging in age between 12-19 is mandatory. Knowledge of and experience in group dynamics, teaching or facilitating groups, supervision of meal planning, food preparation and cooking, and managing logistics. Ability to teach program specific skills, environmental awareness, and related scientific, cultural, and historical knowledge pertaining to the regions through which you will travel and their relationship to each other.


Self-assurance is required to live and relate with adolescents and other Instructors in close-knit situations.


Must be self-motivated and act as a role model, possessing personality characteristics that will accelerate and maintain a healthy rapport with participants and other staff.


Must have the patience to respond to stress, crisis, change, and non-glamorous tasks in positive and productive ways at all times. Must have the ability to organize and assure a smooth flow of activities.

Legal right to work in the United States

PLEASE NOTE: RLT is not able to assist with work visas.

Position Requirements:

The Road Less Traveled offers three summer positions: Trip Leaders, Co-Leaders and Interns. Co-Leaders and Interns work in conjunction with the Trip Leader in a variety of supportive roles. Most first year staff are Co-Leaders. However, if you feel you have the qualifications and would like to apply specifically for a Trip Leader position, please indicate that on your application.

Trip Leaders will plan, coordinate and execute daily activities and trip logistics; monitor Co-Leader and participant assignments for the day; plan and execute the evening programs; act as a positive role model for participants; supervise the health and safety of the participants and environment; manage finances and accounting including monitoring of expenditures, record keeping, advances, and bookkeeping; manage gear, vehicles, inventory, storage and documentation; perform reviews and summer end evaluations; and evaluate programming and current season while making suggestions for the following year.

Dates of Employment:

Dates of employment can range anywhere from mid-June to the end of July or middle of August, depending on your trip assignment. You may lead one, two or possibly three sessions of a program over the course of a summer. RLT will make every effort to employ you for as long as you wish, but flexibility is necessary with trip assignments and dates, keeping in mind the students experience is a direct result of its leadership. If you are a first year staff with RLT, it may be late spring or even staff training before final placement is determined.


Your salary is based on experience/certifications/qualifications and includes all food, lodging and transportation from the beginning through close of your trip. You will also receive a stipend towards certifications, pro-deals on outdoor equipment from a variety of well-known manufacturers and the opportunity to work with world-renown, expert guides!

Application Procedures/Deadlines:

Please fill out an application on this link: Our hiring season runs from September through early May. A large volume of resumes are received during this time period, so it may take a week or more for a reply. There is no official closing date, but the earlier you send in your application, the more likely you will be hired.

Contact Information: 

Director: Jim Stein

[email protected],

2331 N Elston Ave.

Chicago, IL 60614