Compass Instructor (Trip Leader)

Compass Instructor (Trip Leader) Boston, MA $120

• $140 a day
• Temporary, Part-time, Contract $120
• $140 a day

•

Temporary, Part-time, Contract Job Title:

Compass Instructor (Iceland Trip Leader)

Employment Type:

1099

Contractor Compensation:

Daily Stipend (plus all trip-related expenses covered)

Commitment:

Minimum of two trips per year (6-13 days each), plus virtual and in-person trainings

Location:

All Compass programs currently take place in Iceland. Instructors must live within a reasonable commuting distance of one of the following U.S.

cities:

Boston, Nashville, Chicago, Denver, Seattle, or Washington, D.C. Compass covers round-trip travel to and from Iceland from these locations.

PLEASE NOTE

THIS

IS A UNIQUE JOB DESCRIPTION. PLEASE READ IT IN FULL AND VISIT OUR WEBSITE

(COMPASSPATH.ORG)

AND INSTAGRAM

(@COMPASSPATH)

TO FULLY UNDERSTAND THIS ROLE BEFORE APPLYING.

Cover letters are highly recommended as applications that do not reflect an understanding of our mission and work are unlikely to receive a response.

Who You Are:

You're a grounded, flexible leader who cares deeply about young people. You know how to facilitate meaningful conversations and create spaces where people feel seen. You bring emotional and spiritual maturity, a desire to serve, and a steady presence. You're a person of faith—rooted but not rigid—driven more by authentic curiosity than dogma. Whether leading a hike or a late-night debrief, you know how to hold space, lead with humility, and make purpose come alive. What You'll Do Compass Instructors are part personal life coach, part wilderness guide, part travel guru, and part theologian-in-residence. You are the anchor of each trip—leading, mentoring, and holding space for participants as they engage in cultural immersion, community service, and faith exploration. As a Compass Instructor, you'll facilitate transformative service-learning and mission experiences that accelerate purpose in participants. You'll guide individuals and groups through reflection, challenge, and connection—helping them clarify who they are, what they value, and how they want to show up in the world. Your job is to create a safe, dynamic, and growth-oriented environment—spiritually, relationally, and logistically. You'll oversee day-to-day trip logistics while also leading group discussions, mentorship moments, and debrief circles that stick with participants long after the trip ends.

Who We Are:

Compass was founded during the pandemic, born out of an existential moment that demanded people live into their whole selves and deeper purpose. From the beginning, we've been a small staff backed by a committed board and a big mission: to make transformative travel and service accessible to people of all backgrounds and means. We're here to disrupt the travel industry—not just in terms of access, but in the why . We don't run trips for Instagram posts or résumé boosters. We don't show up with a savior complex. We believe that being good global citizens makes us better local neighbors—and the world needs both right now. As a faith-based organization, we're rooted in spiritual connection, but not one-size-fits-all dogma. We value inclusivity, presence, and creativity, and we seek to cultivate purpose in every participant—and in ourselves. We're travelers too, on our own journey toward wholeness. The best part of this work? We get to live it fully, with our whole selves, alongside the people we serve.

Key Responsibilities:

Lead and Facilitate Compass Trips:

Lead and facilitate Compass trips in Iceland, acting as the primary guide and point of contact for participants. You will be the key facilitator of Compass's curriculum, engaging students and groups from diverse backgrounds in meaningful discussions and activities centered around purpose, service, and cultural exchange.

Ensure Safety and Well-being:

Ensure the safety and well-being of all participants throughout the trip, including adherence to Compass safety protocols. Liaison with

Partners:

Serve as the liaison between Compass and Icelandic partners, managing logistics and coordinating service projects.

Leadership and Mentorship:

Provide leadership, mentorship, and support to participants and leaders, fostering a positive and inclusive group dynamic.

Instructor Training:

Prepare for trips by attending a mandatory two-day instructor training on January 14-16, 2026. Compass covers travel and related expenses. Collaborate for

Success:

Collaborate with the Compass team to ensure the successful execution of the trip, including pre-trip preparations (training and logistics) and post-trip evaluations.

Qualifications:

Active Christian Faith Journey:

We're looking for instructors who are on their own journey of faith—curious, grounded, and open. At Compass, spirituality isn't about having all the answers. It's about showing up fully, asking deeper questions, and cultivating connection with God in whatever form that takes. While we serve participants from all backgrounds, we seek leaders who can authentically engage in conversations about faith and purpose, rooted in Christian values and guided by humility, curiosity, and presence.

Mature Confidence and Humility:

We seek leaders who are secure in themselves and their giftings, without feeling the need to prove anything. We value individuals who are deeply gifted at seeing others, using their strengths to help others shine. You should know how to command a room when important information needs to be communicated or decisions are required, but also how to decenter yourself when facilitating experiences and conversations. Our core values of inclusivity, presence, and creativity directly correlate to the type of leader we seek.

Experience Over Education:

At Compass, we believe that expertise and excellent facilitation aren't always indicated by a degree. We do not require a specific level of formal education for this role and welcome applicants from diverse backgrounds. We do require at least 1-2 years of experience in education, trip leading, or facilitation. Ideally, candidates will have participated in a Compass trip before. Those who have not been part of Compass before will participate in an orientation trip prior to being paid as an instructor.

Flexibility/Patience/Organization:

We seek individuals who can navigate stress, crisis, change, and less glamorous tasks with patience and positivity, while embodying Compass's core values of inclusivity, creativity, and presence. Instructors must be able to organize and ensure the smooth flow of activities, while adapting and improvising with creative solutions when necessary, always remaining fully present in each moment.

Personality/Motivation:

We are looking for self-motivated, resilient individuals who can embody Compass's values—fostering inclusivity, thinking creatively, and maintaining a strong sense of presence. Applicants should be able to solve problems independently, build authentic relationships with students, staff, community partners, and administrators, and inspire others through their ability to stay grounded and intentional in every interaction.

Valid Passport and Driver's License:

A valid passport and a driver's license with a clean driving record are required for this role.

CORI Check:

All applicants must pass a CORI (Criminal Offender Record Information) check.

International Phone Plan:

Instructors must have access to a phone plan that works internationally (cellular service, not Wi-Fi dependent) during trips. Compensation for this is included in your stipend. Commitment to

Trips:

We require the ability to commit to a minimum of two trips per year. Instructors must also go on one training trip with another instructor prior to leading their own trips. The expenses of this training trip will be covered by Compass, but is unpaid beyond trip expenses.

Training:

All prospective staff are required to attend our annual staff training.

CPR/First Aid :

A plus but not required. Compass will cover the cost of this training for instructors who pursue it.

Language Skills:

Fluency in Icelandic or Spanish is a plus but not required.

Additional Benefits:

Stipend for each trip, commensurate with the length of the trip All expenses paid for trips, including accommodation, meals, and activities. Paid attendance at a two-day instructor training in January, with travel covered if needed. 2026 Training dates are January 14-16 and will take place north of Boston. Compass reimburses Wilderness First Aid training completed within a year prior to the trip (though this is not required).

Job Types:

Part-time, Contract, Temporary Pay:

$120.00

• $140.

00 per day

Benefits:

Flexible schedule

License/Certification:

Driver's License (Required)

Location:

Boston, MA (Required)

Work Location:

On the road