Will founded Sentinel Overland with a simple belief: confidence is built through competence. With a background in emergency management, military service, wilderness exploration, and adventure planning, he is passionate about helping others develop practical skills and embrace challenge. His goal is to create meaningful adventures that help people discover the freedom that comes from capable self-reliance

​Gilbert is dedicated to creating positive experiences in the outdoors while helping others build confidence on the trail. Known for his sage demeanor and servant leadership, he enjoys sharing knowledge, fostering camaraderie, and helping participants connect more deeply with both the landscape and the people around them.

Josh serves as Sentinel Overland's media specialist, documenting the moments, landscapes, and stories that make each expedition unique. His eye for photography and storytelling helps capture the spirit of adventure while preserving the experiences shared around camp and along the trail. Through his work, guests can focus on the journey while knowing the memories will be professionally preserved.

Ryan brings a practical, hands-on approach to every expedition. With strengths in vehicle maintenance, sawyer operations, and trail problem solving, he helps ensure guests can travel confidently through remote terrain. Known for his commitment and technical knowledge, Ryan enjoys teaching the skills that keep people moving safely and efficiently in the backcountry.