Overland Summers

Hiring:

Summer 2025!

The Leader Application for the 2025 season is now open. 

Imagine a summer of adventure, commitment, and community. Far more than counselors, Overland’s leaders are role models of the highest caliber. Our leaders focus on creating supportive and wholesome environments where each student can flourish.

34 itineraries, 8 countries, 4 continents: that’s a lot of adventure: 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.

We couldn't be more excited for the summer ahead!

Open Arms Fellowship

Available to applicants who self-identify as BIPOC, LGBTQ+, and/or from a low-income background.

Why It Matters

BIPOC, LGBTQ+, and people from a low-income background traditionally are under-represented in jobs in the outdoor industry. The Open Arms Fellowship recognizes the need for increased representation and access to jobs for people in these demographics.

• Representation matters and makes a difference in the experience of our students and fellow leaders. Our staff should reflect the growing diversity – as it relates to race, ethnicity, gender expression, and sexuality – of our student body and the world we live in.

• Socioeconomic status should not be a barrier. Overland needs to do what it can within the framework of our industry to increase access to the outdoors.

How It Works

Applicants should indicate on their application that they would like to be considered for the Fellowship. Returning leaders should reach out to the Leader Hiring team to inquire about the Fellowship. The Fellowship will be granted on a discretionary basis as part of the leader’s employment package.

• The Fellowship includes up to $1,000 in additional financial support separate from compensation.

• Applicants and returning staff can expect to receive detailed information related to the Fellowship in addition to their offer letter and at-will employment contract.

Additional Information About Overland Summers

How to Apply

The application process consists of a written application and resume, three references, and two rounds of interviews. Our Leader Hiring team aims to find a good fit between an applicant and a trip, as well as between co-leaders. We invite you to apply and look forward to getting to know you.

Application Deadlines

Overland has three application deadlines over the course of the year:

• 11/24/24

• 1/26/25

• 3/30/25

Applications will be assessed on a rolling basis. If you plan to study abroad in the spring, please apply by the fall deadline. Overland will continue to read and process apps submitted after March 30th.

Info Sessions

Starting in October of 2024, we will be conducting online and in-person Info Sessions for prospective leaders. It’s a great chance for you to get to know Overland and its culture. For more information or questions about the Info Sessions, email our Leader Hiring team at hiring@overlandsummers.com.

Minimum Requirements & Expectations

• Passion for working with kids in an outdoor environment

• A valid driver’s license

  • While the majority of our trips require leaders to have had a valid driver’s license for at least 2 years, a select few trips do not have this requirement

• The ability to lift and carry 40 lbs or more of gear or equipment

• The ability to pass a swimming test and lifeguard certification course (offered at training)

• CPR/AED and Wilderness First Aid certifications valid through August, 2025 (not necessary at time of applying, and Overland can help reimburse leaders for these certifications)

• A clean driving record, a positive local police check, CORI, SORI, and three written references

• A recent physical indicating excellent physical and mental health

• Some (but not all!) trips require specialized hiking and camping skills, or foreign language skills

Dates of Employment

Our leaders arrive in mid-June for our 10-day Leader Training. At the end of the summer, the entire staff returns to Williamstown for Leader Closing. Leaders depart in early August.

Leader Compensation

Salaries for first year leaders range from $2,500 to $3,000 based on previous experience and the leader’s role and responsibilities at Overland. In addition, Overland pays:

• 50% of the leader’s travel expenses to-and-from Williamstown (up to $250)—Overland also organizes shuttles from Boston and Albany airports, or carpools from other locations (when possible)

• WFA expenses (up to $250)

• CPR expenses (up to $100)

• And, of course, all trip expenses while leading are provided: all flights, accommodations, meals, and activities (for example, rafting, kayaking, mountaineering, etc.). In the field between trips, leaders receive two nights of hotel accommodations and all meals.

Overland also provides access to pro deals as well as discounts on Trek bikes. And, all Overland leaders receive branded clothing and gear (Nike Dri-Fit T-shirts, Hydro Flasks, etc.).