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Overland Summers

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Poor diversity, unforgiving treatment - Trip Leader Overland Summers Employee Review

2.0
11 Sept 2017
Recommend
CEO approval
Business outlook

Pros

Paid (although a shamefully small compensation compared to the company's substantial income) to get to travel, play, and eat in beautiful places.

Cons

Company lacks diversity. Entire full-time staff, 90% of all kids who you mentor on the trip, and nearly all (minus 5 when I was there) of the trip leaders are white, middle/upper class Northeastern people. Easy for any one who doesn't fit/identify with these demographics to feel alone and excluded from the culture. Most of full-time staff, most notably the Founder and Directors, respond with excessive defensiveness when trip leaders make requests to make concrete changes to main concerns (e.g., lack of diversity). Frustrating environment to work in, and to a point very concerning as many of the full-time and returning leaders seem to have "drunk the punch" and refuse to hear anything other than praise for the company. Company also lacks remorse and empathy, especially for new leaders. Treated some first time leaders very coldly, putting all blame for incidents on new leaders without considering the complexities, nuances, and different perspectives of the incidents. Company prioritizes their public relations over justice and fairness. Founder is very harsh, unforgiving, sexist and fears change even when it means positive social progress. Work/life balance is tough. 24/7 management of kids. Had no idea what I was getting into despite the 10-day training prior to setting off on our trip. Company is not completely transparent about how demanding the job is. They promise 8 hours of sleep as part of the benefits when really most leaders were getting an average of 5, especially if they weren't in the wilderness where the lack of activities is more conducive to a good night's rest.

Explore other reviews about Overland Summers

5.0
24 Nov 2025
Recommend
CEO approval
Business outlook

Pros

The Overland experience is truly unique and special. As a leader in New England and Spain, I had the wonderful opportunity to share two life-changing summers with the incredible Overland community. In an increasingly digitized world, Overland trips provide students and leaders the opportunity to take a step back and build lifelong connections in a technology free environment. With thoughtfully designed trips that are simultaneously safety and goal-focused with attainable challenges, each Overland experience allows students to grow as leaders and gain an appreciation for the wonderful communities that surround us in our stunning natural world. From practicing a foreign language in a remote village to cheering each other on as we tackle challenging trails together, every Overland trip has the potential to be a transformative experience for students and leaders alike. I can genuinely say that I am who I am today thanks to the amazing community that makes these experiences possible. I could not recommend Overland enough to prospective students, parents, and leaders!

Cons

As with any trip leader position, the job naturally requires a full commitment for 24 hours a day and multiple weeks in the field. Developing a strong co-leading relationship is crucial to maintaining high energy and motivation for the duration of the trip. Adequate training is provided in this area.

4.0
15 Jul 2025
Recommend
CEO approval
Business outlook

Pros

Working with kids is super rewarding and fun, get paid to be outside and camp, hike, and bike all day, co-leaders were great to work with, good community of co-leaders with a fun two week training at the beginning of the summer

Cons

Working 24/7 with no real days off for 8 weeks is exhausting. This was the most sleep deprived I’ve been in my life and took weeks after getting home to recover physically and mentally. Pay was way too low.

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