Join Our Team


We welcome your application to join our year-round team.

The Overland year-round team is a group of professionals dedicated to advancing our mission to inspire our students to see how beautiful and exciting, how full of promise the world is. We are recent college grads; we are part-time employees and full-time moms; we are fathers and coaches; we are hikers and bikers; we are East Coasters; we are West Coasters; we are inclusive and welcoming.

Based in Williamstown, Mass., we are members of a small-town community in a beautiful corner of New England. The seasonality of both Williamstown and Overland imbues each phase of the year with varied tasks, projects and responsibilities. Beginning in September, our work builds towards peak admissions season in the winter, then transitions to summer preparation in the months between January and June. Our six-week summer season is a time of energy and action; it’s the goal we’ve been striving towards all year. For over 32 years, Overland has created superlative trips and lasting experiences for our students – as a team, that’s what drives us forward.


Admissions & Financial Aid. Responsibilities include generating over 2,500 applications for each summer’s trips, traveling across the country to make presentations, working with parents over the phone and via email and overseeing our financial aid program, Open Arms. As with every position at Overland, members of the admissions and financial aid team will have additional responsibilities that will include assisting with leader recruitment and other tasks. CURRENT STATUS: All positions filled.

Leader Hiring. Responsibilities include recruiting, evaluating and hiring summer trip leaders from colleges and universities across the country. The leader hiring staff works with our current and former leaders to fill approximately 100 spots for each summer’s staff of trip leaders and then generates over 1,000 applications each year for the remaining approximately 100 spots for new leaders. As with every position at Overland, leader hiring staff will have additional responsibilities that will include assisting with student recruitment and can include other tasks (e.g., trip planning and/or managing equipment). CURRENT STATUS: All positions filled.

Trip Planning. Responsibilities include managing a group of trips throughout the year, starting with a September review of the previous summer’s experience and progressing through revisions in the fall (which can include travel to scout locations), reservations in the winter and dialing in the details in the spring. When our summer season begins, trip planners manage their trips from our offices in Williamstown, working with leaders in the field to ensure the smooth operation of their trips. As with every position on the Overland staff, trip planners will have additional responsibilities that will include assisting with leader and student recruitment, managing equipment and other tasks.

CURRENT STATUS: All positions filled.