Our Leaders

Far more than simply counselors or guides, Overland’s leaders are terrific role models for our students.
Capable and caring, our leaders focus on creating supportive, wholesome environments where every student can flourish and grow.


Lead for Us
  • 1000 applicants

    We recruit our leaders from America’s finest colleges and universities, meeting with hundreds of campus leaders across the country—an effort that generates almost 1000 applications each year.

  • 300 minutes

    We typically spend over five hours evaluating our finalists: there are two readings of the application, a thorough review of three references, a three-part background check and an interview.

  • 200 leaders

    In 2019, we had almost 2020 leaders on staff. A mix of first year and returning leaders, our leaders include top students, athletes and campus leaders—ideal role models for our students. 

  • 50 colleges

    We visit the campuses of the country’s top schools multiple times during the year and rely on our network of leaders at these schools to produce a deep pool of qualified applicants.

  • 10 days

    All of our leaders come to Williamstown for 10 days of training in June. Leaders arrive certified in First Aid, CPR and lifesaving, so training can focus on logistics, group dynamics and communications.

  • 1 goal

    Our talented leaders have one goal: the success of each of their students. This, perhaps more than anything else, has made the difference for us as an organization and for the thousands of students who have joined us.

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Become a Leader for Overland