Leader FAQs

Who are Overland Leaders?

Overland leaders are bright, dynamic and accomplished college students and recent graduates from America's best colleges and universities. Overland leaders are motivated by the desire to have an impact on the lives of the students they lead, while enjoying the camaraderie of inspiring colleagues and the excitement of travel.

Far more than counselors, guides or instructors, Overland leaders are wonderful role models for our students, inspiring these young adults to understand the importance of friendship, consideration, teamwork and determination. Caring, motivated and fun, our staff of over 130 leaders ensures the safety and well-being of every Overland student.

Leaders have completed at least their sophomore year of college, worked with kids and had extensive leadership experience--typically through high school and college leadership positions (e.g., sports teams, student government, outing club, service organizations, language clubs, etc.). Last summer, more than 50 leaders returned to Overland for a second, third, fourth or fifth summer.

What Leadership Opportunities does Overland Offer?

Leaders:

The majority of Overland leaders have completed at least their sophomore year of college and have impressive leadership experience both in high school and on campus at their colleges. We do our best to put together pairs whose strengths complement each other and whose personalities seem likely to work well together. Leaders work in co-ed pairs. We do not have a senior leader and a junior leader; our leaders are equals who strive to create a family-like environment within the group. We will occasionally have couples on staff but we will not place them together as leaders.

Support Staff:

Our dedicated support staff are the backbone of the entire Overland operation. Primary responsibilities include assisting with program logistics, especially at the start and end of each program, managing gear and providing office support for leaders in the field. Additionally, some support staff may be scheduled to lead a program as a part of their summer duties or provide hiking support for leaders in the field. Support staff fully participate in leader training. All support staff must have completed at least their first year of college.

"I love Overland because it asks you to be the best person you can be and rewards you greatly for doing so." Nick Williams, Vanderbilt University '10; Paris to the Sea '10, Blue Ridge Explorer '08, Summer Writing Program, New England Adventure & Support Staff '07

What is it like to lead for Overland?

Challenge and Growth

Leading an Overland program is one of the most challenging jobs you can imagine, but it's also one of the most fun and fulfilling. Our focus on small, supportive groups and carefully crafted programs allow both students and leaders to have fun, develop close friendships, be challenged and grow through their experience.

"From the moment you arrive at leader training you feel part of something completely amazing." Reid Berrien, Middlebury College '08, Field Studies Tanzania '10, European Explorer '09; Yellowstone Teton Explorer '08; New England Explorer '07

Leader Training

Summer begins for all with ten days of leader training in Williamstown, Mass. Through delicious meals, camping and leadership seminars, new leaders come to understand Overland traditions and culture from long- tenured directors and returning leaders. Leader training also includes multi-day hiking or biking trips in the beautiful Berkshires. This training trip gives you an incredible opportunity to get to know your co-leader and focuses on creating a positive group dynamic. During leader training, you and your co-leader will learn about the logistics of your program, the backgrounds of your students and the fundamentals of Overland's approach to leading students through a great summer.

"It felt amazing to be part of such a close, strong and ambitious community, and between the amazing people I got to work with and the great experiences I could offer students, I can't think of anything I would have enjoyed more. " Eric Edelstein, Dartmouth College '13; Berkshire Adventure & Support Staff '10

Commitment to Overland

Once your program starts and your students arrive, you'll find that your days are exciting, fulfilling and fun--and that they are long, tiring and demanding: you will lead 24-hours-a-day, 7-days-a-week on programs that last from one to six weeks.

At the end of your program, you will return to Williamstown for a few days to reflect on your experience, your students and your program's logistics. These days are again filled with delicious meals, laughter and friendship. Leader closing serves as a fitting end to your Overland summer as you reconnect with the rest of the staff and share stories from your travels and adventures around the world.

"Working for Overland exceeded all my expectations of both what I could put into and what I could get out of a job.  On a day-to-day basis I applied more consistent concentration and effort into what I was doing that I would have thought possible, and also had more genuine fun than I could have imagined." Carolyn Lucey, Columbia University '13; Mountains & Sea Adventure '10

Why lead for Overland?

When we ask our leaders for just one reason to spend the summer with Overland, we get a variety of answers. Spending time with kids. Having fun. Being challenged. Working with inspiring peers. Exploring the world. Serving as a role model. Being part of a spirited community. Developing strong friendships. Making a difference. All Overland leaders agree, however, that it is the unique combination of all of these reasons that make working for Overland such an amazing opportunity.

"This summer I learned about myself as a leader, more than anything else.  I am proud of the work I did this summer and the leader and mentor I was able to be for our students." Eliza O'Neil, Bates College '09; European Explorer '10

What do Overland leaders have to say about leading for Overland?

"Sharing my love of the outdoors and providing a wholesome environment for kids to be themselves, grow personally and learn about the importance of sacrificing for a group and a goal is an amazing opportunity.  Overland provides me a beautiful opportunity to simplify and invest myself wholly in one thing... in the group."
Dave Clark-Barol, Middlebury College '10.5; European Explorer '10, Yellowstone Teton Explorer '09, New England Explorer '08

"I had another wonderful experience with Overland this summer.  I was grateful for the immense ammount of trust that the office staff placed in my decision making abilities and in my actions as a leader.  This independence empowers leaders more than any other action could; once you realize the trip is in your hands, people step up to meet a new challenge with every ounce of energy."
Hannah Phillips, Skidmore College '09.5; Alaska Leadership Course '10, High Sierra Explorer '09

"Overland was awesome!  The office was unbelievable and my co-leader was outstanding.  I think it was a great experience for our whole group to gain more perspective on ourselves and the world at large  ."
Erik Anderson, Williams College '12; Alaska Leadership Course '10

"My summer was incredible.  Overland has been so important in the development of my confidence and character.  It has been an incredible run of three years, each year improves upon the last.  The office environment and the attitude of the leaders make for an empowering landscape.  Overland sets the bar very high."
Caroline Turnbull, Colby College '10; American Challenge '10, Nova Scotia & Acadia & New England Coast '09, Cape Cod & the Islands & Vermont '08