Our Team
A message from the directors
Welcome to Apogee’s 24th season! Since 2001, we have passionately delivered fun, life-changing summer experiences to young people. In the summer of 2025, we expect to welcome more than 500 students to the Apogee family and run more than 50 adventure and service trips.
Accredited by the American Camp Association, our program continues to thrive because we know that top-notch leadership and a personal connection are both key to the success of our trips. Our trip leaders are, quite simply, the very best you will find. And at Apogee, we know each student by name and invest in them individually. Parents will feel welcome, too – we’re always available and excited to speak with you. This warm, family atmosphere is what we’re all about; it’s what allows Apogee students to flourish and parents to feel at ease.
If you’re already part of the Apogee family, we can’t wait to see you again. And if you’ve never spent a summer with us, we hope 2025 is the year you do! Please join us!
Sincerely,
Kevin Cashman, Founder/Director
Will Robertson, Director
Chad Olcott, Advisory Director
MORE ABOUT OUR YEAR-ROUND TEAM
Miles Bent
Assistant Director
Miles was born and raised in Virginia’s beautiful Shenandoah Valley, hiking and exploring the Blue Ridge Mountains. A 2017 graduate of Washington and Lee University (W&L, for short), Miles studied Global Politics and English, played varsity soccer, and served as a peer counselor to incoming first-years at the college. Miles was first introduced to Apogee while at W&L, and went on to lead Maine Coast College Essay in 2015, Pacific Coast in 2017, Europe Coast to Coast in 2018, and Vermont to Montreal in 2021. Before joining Apogee’s full-time team in January of 2022, Miles spent his previous four years in Washington, DC, where he worked as a cybersecurity consultant, a bartender and as a Program Manager at a youth outdoor education non-profit. When he’s not at the office you can find him running with his dog, playing soccer, biking, snowboarding, reading, or playing board games with anyone who challenges him.
Kevin Cashman
Founder & Director
Kevin grew up in Westfield, NJ and attended Dickinson College. Since graduating from Dickinson in 1995, Kevin has worked almost exclusively in the outdoor adventure travel field. In 2001, after working for years as a trip leader and director for other outdoor programs, Kevin followed his dream and founded Apogee. His passion and perseverance for Apogee have paid off through the years and have resulted in a thriving, highly respected program. Having led the trips in Apogee’s early years, Kevin knows exactly what goes into crafting a successful adventure. One of his greatest satisfactions is making connections with Apogee students and their families. He has an uncanny ability to remember names and details about many of the thousands of students who have taken part in the program over time. In addition to loving his job, Kevin is an avid runner, cyclist, and outdoorsman. He loves to travel, especially by bicycle. Kevin is a Licensed Cycling Instructor with the American League of Bicyclists. He lives in Brunswick, Maine with his wife, Birgitta, and their two boys, Sam & Jack.
Shem Dixon
Associate Director
Shem was raised in the fresh air and among the mountain streams of western Maine. A 2011 graduate of Bowdoin College, Shem double-majored in Biology and Earth & Oceanographic Sciences while honing his leadership and communication skills in various roles in the College’s Residential Life program. With Apogee, Shem led our Coast to Quebec and Pacific Coast bicycle-touring trips before joining Apogee’s year-round team in September 2013. For many years, Shem coordinated logistics and risk management for Apogee’s adventure programming. While still a jack-of-all-trades, he now focuses his energies mostly on student enrollment and managing our invoicing and travel protection policies. Shem lives in Brunswick with his wife (whom he met through Apogee!) and spends as much time as he can outdoors adventuring with their dog, Maggie.
Laura Girr
Enrollment & Administration Specialist
Laura grew up in Southern Maine and attended the University of Maine at Orono where she studied German and Spanish. Laura spent many years teaching World Languages courses to high school students, and in the early years of her career, used her summers to lead language immersion and educational trips in Europe. Seeing the promise of technology as a communication tool to connect her students with real world language practice, Laura pursued a Masters in Educational Technology at Lesley University, and transitioned to a job as a Technology Coordinator and Integrationist. Laura has two grown children who are rock stars (one literally, one figuratively): Mia, an eighth grade social studies teacher, and Drew, a musician. Mia was a two-time Apogee student and later went on to lead for Apogee for six summers, solidifying her status as an “Apogee Legend.” Laura recently moved to Brunswick and is excited for the opportunity to spend more time with the hard-working, fun-loving Apogee staff and leaders.
Jack Messerly
Associate Director
Jack, a loyal Minnesotan, grew up fishing and playing pond hockey with his family near the Twin Cities. Jack attended Hamilton College where he studied math, captained the Men’s Rugby team, spent a semester adventuring in New Zealand, and led wilderness pre-orientation trips for incoming first-year students. He spent three summers in the field with Apogee, leading four different trips (New England Mountains & Coast, Maine’s Downeast Explorer, California Mountains & Coast, and Alps Explorer) before joining the full-time Apogee team in 2015. Now, Jack lives in Brunswick with his wife (and former Apogee Assistant Director), Izzy, and the newest members of the Apogee family: their sons, Tucker and Weston. When he’s not coordinating Apogee’s Staff Recruiting or hiking with his family, you can probably find Jack studying poker theory or cooking up something tasty in the kitchen.
Chad Olcott
Advisory Director
Chad up between the hills of Western Massachusetts and the palm trees of Miami, Florida before attending Bowdoin College in Apogee’s hometown of Brunswick, Maine. After four summers of leading and supporting outdoor adventure trips throughout the United States during and after college, Chad was hooked on the adventuring lifestyle. Nonetheless, he spent six years practicing law, first as a JAG with the U.S. Navy in San Diego, California and Sardinia, Italy, before joining a law firm in Portland, Maine. In 2009, the siren song of the outdoors and experiential education proved too much to ignore, and Chad was delighted to join Kevin at Apogee. He finds his current mission – furthering Apogee’s goals of instilling personal confidence, character, and community-mindedness in every student – to be the most fulfilling work he could imagine. Chad lives in Brunswick with his wife, Susan, and their twin daughters, Liliana and Phoebe. In addition to his work with Apogee, Chad sits on the board of directors at Paradox Sports, a non-profit dedicated to transforming lives and communities through adaptive climbing opportunities.
Will Robertson
Director
Will grew up in the city of St. Paul, Minnesota before heading east to study at Hamilton College. When he wasn’t roaming the halls of Hamilton’s music department, Will spent his college years running with the cross country team and working for the Hamilton Outdoor Leadership Program. After college, Will spent three years working in the Twin Cities, but would put his jobs on hold in the summertime to pursue his true passion: leading Apogee trips. After three summers of trip leading, Will was fully hooked on Apogee’s mission and joined the full-time Apogee team in the spring of 2017. Over the past seven years as an Associate Director, Will has been involved in all aspects of Apogee’s operations, from leader hiring and training to risk management and trip logistics. In the fall of 2024, Will joined Kevin and Chad as one of Apogee’s Directors. After ten years at Apogee, Will continues to find joy in creating opportunities for students to be their true, authentic, selves on Apogee trips – allowing students to connect with their peers in a supportive community without today’s pressures of social media and technology. Will lives in Brunswick, Maine with his wife, Mackenzie, and their two cats (Merry and Pippin, in case you were wondering…).
Jackie Weik
Assistant Director
Jackie grew up biking, waterskiing, and hiking in northwest Connecticut. A recent graduate of the University of New Hampshire, Jackie studied Communication and Studio Art, was the recipient of UNH’s Photography Fellowship, worked at The New Hampshire newspaper, and managed public relations for multiple university organizations. Jackie was actively involved with the New Hampshire Outing Club during her time at UNH, leading hiking and backpacking trips in Maine, California, and New Hampshire. She took on various roles within the club, serving as the Publicity Chair and President. Prior to joining Apogee in the Winter of 2023, Jackie spent 3 months traveling through Spain and Portugal, with a portion of that time spent hiking the Camino de Santiago. When she’s not at the office you can find her exploring Portland, taking photos, waking up early to catch the sunrise, or heading out to the White Mountains for the weekend.
