About Us

together, we serve our personal and corporate clients with the highest level of expertise, integrity and passion. 


Phil Bailey

Expedition Leadership


Safety & Risk



Global Corporate


Headshots Phil-15.jpg

Meet Phil Bailey

Phil has spent over 25 years in the field managing hundreds of thousands of hours of human behavior in high-stress and even crisis conditions. He has earned his reputation as an expert in expeditionary and tour-based leadership, operational risk management, and functional training. 

There are no shortcuts in this industry. Phil has cycled, climbed and trekked thousands of miles across the U.S. and abroad and has complied over 2,000 field days leading expeditions and cycling tours for outdoor education programs and private groups. 

Phil's clients trust him because he has amassed a comprehensive number of certifications in safety, emergency medical training and basic life support, and sports/injury recovery training with highly-driven professional and amateur athletes. 

They continue to work with him because of his passion for training individuals and companies to reach their maximum potential. 

Phil frequently consults with small companies to large firms to help CEOs and HR strategists promote accountability and collaboration and improve employee recruitment/retention through effective human capital management based on expedition leadership theory.

He details his corporate training approach in his most recent book, "Expedition Boardroom." Learn more about this book and other Functional Adventure publications



Wilderness & Outdoor

Phil has tracked more than 1,000 field days as an expedition leader or expedition staff trainer for Outward Bound, Trek, Odyssey and others. He has also cycled thousands and thousands of miles as a tour leader. 

  • Wilderness EMT (WEMT), Advanced WEMT and WFA/WFR Instructor, 1997-2016

  • Wilderness First Responder (WFR) & Basic Life Support (BLS) Certification

  • Safety, Operations & Risk Management Consultant to the general outdoor recreation industry

  • America Mountain Guides Association (AMGA) training 

  • REI Outdoor School Cycling and Rock Climbing senior instructor

  • American Canoe Association (ACA) Sea Kayak instructor

  • Lead instructor and field director for various wilderness therapy programs

  • Lead Guide for Luxury Cycling Tours, managing all aspects of week-long tours covering 400 miles of challenging terrain

  • 2019 Haute Route Pyrenees Competitor - check back in August for results!


Phil has worked as a consultant to the general outdoor industry and higher education since 2011, following a long career in the field as well as senior-level administration. Phil's practice focuses on policy design, human capital management, operational risk management and new program start-up.

While acting as the consulting director of operations for a large real estate company, Phil applied his previous experience as a stockbroker and small business owner to merge the worlds of the high-stakes corporate landscape and high-consequence adventure programming to create the Key Skills Integration Model (KSIM) and his Risk Management & Judgment Matrix (RM&JM).

Key experiences include:

  • Outward Bound Professional (OBP): Facilitator for corporate clients

  • Thompson Island Outward Bound Education Center: Consultation for policy design, program creation, and several safety audits

  • Boston University Questrom School of Business: Consultation on content and curriculum design for their highly-rated organizational behavior program

  • Unity College (Unity, ME): Guest lecturer for several semesters speaking on matrix design for measurable professional competency and accountability

  • Atlantic Challenge (Rockland, ME): Policy, risk management and program design

  • Association for Experiential Education (AEE): Northeast Regional conference co-convener, presenter and multi-year sponsor

  • Heroic Journey (Golden, CO): New program startup including business plan and funding model, now operated by Outward Bound

  • Peak & Paddle Croatia: Collaboration to create a corporate training bicycle touring program from the Italian Alps through Slovenia and ending in Croatia

  • Project U.S.E. (Newark, NJ): Staff development, risk management and policy design

  • Outward Bound Croatia: Consulting with the board safety committee on all aspects of program design and risk management


Meet Our Team



Smithwood-Green, MAOP

& talent Management strategist

Jenn brings a diverse background, comprised of both therapeutic and wilderness-based program instruction, in addition to extensive experience in non-profit administration and human capital management.

For several years, Jenn served as the VP of Organizational Development for an Outward Bound school where she oversaw the growth of a large, complex non-profit that serves several user groups and provides many different service lines.

Jenn’s responsibilities included recruiting, hiring, training, development and management of a staff that numbered up to 150 people in high season.

Jenn holds a Masters in Organizational Psychology, and focuses on offering strategic direction and support to organizations seeking to engage, develop, and retain top talent while effectively designing and facilitating activities that strengthen team dynamics and further contribute to positive, collaborative and productive work environments.