The Bicycle Industry Jobs Marketplace

Overland Summers is Looking for Trip Leaders in Canada, Europe and US and Africa


Posted by Overland Summers on 01/12/2022

Job Basics

Industry Sector: Bike, Outdoor

Job Categories: Camp Staff & Counselors, Outdoor Education, Outfitter- Adventure Travel Staff

Company Type: Recreation, Service, Retail, TravelandTourism

State: MA

City: Williamstown

Country: United States

Required Experience: 0 - 1 year

Contact Name:

Job Type: Seasonal Full Time

Salary: $2,500-$5,000/season

Required to Relocate:

Required to Travel: Yes

Employee May Telecommute: No

Job Seeker Must Live Within:

Job Description & Requirements

Imagine a summer of adventure, commitment, and community.

40 itineraries, 12 countries, 3 continents: that’s a lot of adventure. But leading at Overland isn’t really about where you go, and in some important ways, it’s not really about what you do. Instead, leading for Overland is about the people who surround you — the dynamic leaders you work with and the great kids you lead — and the many challenges, both big and small, that you tackle together.

An Overland leader’s commitments are many, but nothing is as important as your co-leader and your kids. No matter where you are, no matter what you’re doing, your most important commitment is the health and well-being of those around you. This commitment drives and informs your leadership every moment of every day.

The Overland community is supportive, wholesome, and empowering. In all we do, we seek to create a culture of respect. We welcome students and leaders from across the country and around the world, we seek to offer broad access to our trips through our Open Arms scholarship program, and we value a range of life experiences and perspectives in our leadership staff. As an organization, we are engaged in continuing the conversation regarding diversity and inclusion in outdoor communities. We recognize that the issues of inclusivity and accessibility within outdoor culture are complex and present issues. In recent years, our hiring team has focused on reaching out to colleges and campus organizations to cultivate a more diverse pool of applicants. Yet, quite frankly, we recognize that we, and our peer institutions, have a long way to go to living out our ideals of equity and representation. We’re eager to partner with leaders so that we can learn and continue to get better. Overland does not discriminate on the basis of race, color, national or ethnic origin, familial status, genetics, ancestry, religion, disability, sex, sexual orientation, gender identity and expression, or any other characteristic protected under applicable federal or state law. These values have been a part of Overland for nearly four decades, and they’re important qualities that we look for when choosing new leaders.

Overland leaders stay connected in a vibrant community that stretches beyond the summer, beyond leading. For over 35 years, Overland leaders have stayed connected—as former leaders, friends, and colleagues—and these relationships, which started in a single summer, have grown in countless ways. The Overland community is a powerful network full of not only strong friendships, but also connections to job opportunities worldwide. Overland leaders go on to attend graduate programs, teach abroad, and work in a wide variety of professional fields.

In the end, leading for Overland is far greater than the sum of its parts — exciting adventure, great people, important commitments, endless challenges, a supportive community, and a vibrant network—but there’s more, too. There’s the chance to deepen and broaden your leadership skills while discovering just how beautiful and exciting, how full of promise the world is.

We encourage you to apply to join us. Everyone on the Overland year-round staff is eager to read your application and to meet you. We look forward to hearing from you!