OVERLAND CAREERS

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Join Our Team

Become an important part of a great team

The Overland year-round team is a group of dedicated, motivated, high performing, and adaptable professionals dedicated to advancing our mission. Everyone plays a part in getting our students outside, where they are challenged and empowered to become the best possible versions of themselves. We place a premium on selflessness, teamwork, and a consideration for others, all things that allow our students to appreciate the beauty and promise of the world around them. We are a small team based in two locations: Williamstown, Massachusetts and Bozeman, Montana.

The seasonality of Overland imbues each phase of the year with varied tasks, projects, and responsibilities. For most of the year, our office is open Monday through Friday. However, our work is seasonal. During our peak student enrollment season (January and February) and during our summer season (June-August) salaried members of our team receive one day off every week. Our six-week summer season is the busiest time of the year; it’s the goal we have been striving towards all year. For over 40 years, Overland has created superlative trips and lasting experiences for our students—as a team, that’s what drives us forward.

Annual opportunities

Our office is divided, predominantly, into three distinct teams: Admissions, Leader Hiring, and Trip Planning. Applicants will be placed onto one of these teams and are welcome to denote specific interest in one, or multiple, of these teams within their application.

Applicants for all positions should have excellent organizational skills, attention to detail, and the ability to communicate clearly. We seek team players who are eager to be a part of a dynamic organization where we share responsibilities, support each other, and celebrate our successes.

Admissions

In our most family-focused role, members of the Admissions team will work with families to get students enrolled for trips. Primarily communicating via phone and email, members of the Admissions team should be patient, professional, and personable. See a more comprehensive description here.

Leader Hiring

Members of the Leader Hiring team are responsible for recruiting, evaluating, and hiring our summer leading staff. This role requires strong communication skills along with superb judgment. See a more comprehensive description here.

Trip Planning

Members of the Trip Planning team will be responsible for managing a handful of our different trip itineraries. You will be responsible for permitting, planning, and budgeting for 6-8 different itineraries. Strong organization skills and an independent work ethic is crucial to success within this role. See a more comprehensive description here.

how to apply

We expect to conduct several rounds of interviews for the 2025-26 season in March of 2025. We typically make most final hiring decisions by April for staff starting the following September. We expect to hire for in-person roles in Bozeman, Montana.

Please send a resume, brief cover letter, and transcript (if applicable) to [email protected]

Salary and Benefits

Salary

Overland offers a competitive salary to interested candidates commensurate with experience. Salaried members are eligible for an annual raise.

Benefits

401k Tax-Sheltered Retirement Plan with a 3% company match
Health Insurance
Gym/Ski Passes: Overland reimburses $500 per year towards gym memberships or ski passes.
Access to industry specific pro-deals ranging from gear to apparel

Work Hours, Expectations, and Paid Time Off

For most of the year, our offices are open Monday through Friday from 8:30-4:30pm. This role requires 3-5 weeks of travel a year, sometimes for a week or more at a time. Office wide holidays are listed below:

National Holidays: Indigenous Peoples’ Day, Presidents’ Day, Memorial Day.
Friday afternoons (starting at 1:00) in September and October.
Thanksgiving Week: The office will work remotely on Monday, and Tuesday. The office will be closed Wednesday through Friday of that week.
Winter Holidays: The office will close for approximately five work days in addition to Christmas Day and New Year’s Day.
Spring Break: Five days to be taken after the first Friday in March and before May 1.
Summer Vacation: Approximately four weeks at the end of our summer season.

What We Look For

Requirements:

Undergraduate Degree
Experience in Outdoor leadership or Outdoor Education roles
Excitement to work in a collaborative environment where employees share responsibilities and support each other.
Experience in customer service
Ability to speak with audiences ranging from 20 – 200 comfortably

In addition, employees are expected to maintain a valid Wilderness First Aid certification or higher. While it is the responsibility of the employee to maintain these certifications, Overland will offer a partial reimbursement for certification and recertification courses.

If you don’t have experience in all of the above, do not fret! Studies have shown that women and people of color are less likely to apply to jobs unless they meet every single qualification. Not every individual currently working in our office met every qualification upon being hired. If you think you would be a good fit, we encourage you to apply.

Please Reach Out

Throughout the year, we are happy to hear from you if you’re interested in a full-time or part-time role at Overland. Cheers!