To say that Outward Bound instructors are masters of their craft would be an understatement. The quality and safety of our programs are predicated on their professionalism and dedication. They are tasked with simultaneously acting as an educator, trail guide, nurse, and mentor for their students, students who have often been placed in an unfamiliar environment for the first time. Our instructors work tirelessly to create impactful learning experiences, and always place their student’s needs before their own. However, the current pay and benefit models across the outdoor industry are not conducive to retaining instructor morale or even the instructors themselves.
In response to the needs of our program staff, the Chesapeake Bay Outward Bound School (CBOBS) looked to reinvent pay structures to better support our team of experiential educators. In 2021, CBOBS introduced a revolutionary new payment model for our instructor staff. We’re so excited to highlight how our salaried pay is an improvement over Per Diem, the positive changes we’ve seen since implementing it, and ways in which we’re working to continuously improve it. We’ve compiled compelling firsthand accounts from current instructors describing how the shift to this new model has affected them.
Prior to the introduction of the salaried pay model, instructor staff at CBOBS were all part time workers paid “Per Diem” – that’s ‘per day’. In other words, getting paid for every day they work, in contrast to salaried employees who get paid the same amount yearly no matter how many days they work. Per Diem pay remains the standard for a vast majority of employers in the outdoor education industry.

SHORTCOMINGS OF A SINGULAR PAY STRUCTRE
Under our current system, instructors start on Per-Diem pay and are eligible for salaried pay with benefits after completing their first year. When Per-Diem is the only available pay model, it creates significant challenges and barriers to entry for many employees. While the Per Diem system allows for flexible part-time schedules, it can also lead to a lot of uncertainty. Paychecks fluctuate month by month. The nature of our seasonal, outdoor work makes it more difficult to hold a second part-time job. In addition, our programming schedule is not evenly dispersed year-round. Like many other programs, we have a busy season and a slow season. If an instructor has an unplanned unavailability, due to medical issues or family emergency, they might lose crucial working days.
“You need to have a lot of privilege and resources and a buffer of income to afford to move someplace to work for only 3-5 months and get paid very little. If you do have preexisting expenses, pets, an existing lease, a family, it can be really hard to start up as a new staff because you do already have these things you’ve invested in.”
Rachel W., Instructor*
A significant issue for many is that Per Diem pay does not provision for healthcare or other benefits. Even if you are fortunate enough to be enrolled in a parent or guardian’s policy, that coverage ends once you turn 26. Many employees, justifiably, seek other work once they reach this point. This creates a soft cap on the age and experience level of the instructor staff.
“Without this model, I assumed that once I turned 26, I would leave to find a different job that provided insurance”
Ty F., Instructor
Ty, now a Course Director, reflects on the impact of the new system by comparing it to his first year as an Instructor. “I remember when I got here in 2021, there was one instructor entering her third or fourth year. She was amazing, but everybody was saying ‘this is the best instructor we have. She has so much experience and has been here so long‘. It’s crazy to look back and realize that’s where I am right now. That’s where 4 or 5 of my really good friends are. We’re all entering our fourth year at CBOBS, when before there was only one person who had that level of experience, and it was treated as the pinnacle.”

THE BENEFITS OF BENEFITS
So how exactly does a salaried pay system solve these problems? One of the most apparent factors is that it stabilizes instructor salaries. Salaried Instructor staff are paid much like schoolteachers, working 9 months out of the year but receiving those 9 months of pay across a full calendar year. This means that instructors will know exactly how much they’re earning each month and each year – which helps both their budgeting and our own. CBOBS doesn’t run programs in the winter months, so instructors have that useful chunk of time for their own personal endeavors.
“It is really exciting to have something that offers stability but also offers adventure. Too often, it feels like you have to give up one to have the other. The salaried model is absolutely huge for us”
Rachel W.
Lead Instructor Rachel W. works as a substitute teacher over the winter break, and likes that she doesn’t have to try to communicate a fluctuating schedule ahead of time. Additionally, paid winter breaks can also be a time for personal and professional growth. In Rachel’s words, “People who love Outward Bound also love having personal time for adventure, challenge, and discovery.” Plus, that personal growth can translate directly to core competencies that further improve an instructor’s skillset.

Additionally, salaried Instructor staff receive a benefits package that includes healthcare. This means that seasoned instructors have more incentive to stay here. When the average experience level of instructors goes up, it comes with a slew of benefits. New instructors receive more competent training and veteran instructors are able to assist in the professional development of their peers. Rachel puts it best, “Before we had FTE [our salaried pay model] , oftentimes instructors would stay for a few years and move on. As you were learning and training, you were getting bits of knowledge from certain people but it wasn’t really all cohesive. With FTE there seems to be a really strong base of knowledge and many more staff who really know what they’re teaching.“
BUILDING COMMUNITY AND RETENTION

In 2024, most of our lead instructors are now in their fourth year of instructing at CBOBS and are very skilled at facilitating courses, mentoring fellow instructors, and delivering training. This depth of experience has a huge impact on program quality and safety. Since implementing the salary with benefits model, our data shows a significant increase in instructor staff retention. In addition, we see a year over year self-reported increase in perceived leadership support and career satisfaction, which are protective factors against burnout.

Rachel told us how apparent these changes were at the start of the program season. “We walked up for our kickoff day this year and our Expedition Program Coordinator went “I have never seen more competent instructors in one spot.” They were astounded. So, I see it working and I see it benefiting new staff and developing instructors. Lead Instructors, who’ve been instructing for years now get to go on co-leads, offering more cross training opportunities. They get to have a lot of support in the field. In the past, if you were a Lead, you were out there on your own. I’ve had opportunities this year for the first time to co-lead and learn new things from the other staff here, which was an awesome experience.
The benefits that everyone experiences from having a competent cohort of instructors are huge. A lot of people stay at this job for a long time because of the incredible community and relationships that they build here. Working with students at this job really creates a tight knit bond. That community is a huge part of instructor retention and Outward Bound as a school invests in community.”

ONWARDS AND OUTWARD (BOUND)
CBOBS’ leadership is deeply committed to the full-time salary program and our goal is to expand this model to make the work we do more feasible and more attractive for new staff who are just starting out, thus making work in the outdoor industry more accessible for all. The value of the full time model in terms of the experienced pool of instructors and more equitable work environment it creates are invaluable benefits in our mission to change lives through challenge and discovery.
Given the measurable benefits of the salaried program, it only makes sense for us to continue to iterate and improve upon it. We stand behind this model as an important aspect of the work we do and strongly encourage other nonprofits, especially those operating in the outdoor industry, to consider the growing benefits of similar payment models.
If you are interested in learning more about the amazing work our instructors do, or looking to start your career here, check out our instructor webpage. What we do wouldn’t be possible with our amazing community of donors. To help support this exciting and beneficial payment model, consider making a contribution. If you’d like to learn more about what we do and all the different ways you can engage with us, check our latest updates or follow us on social media.

*Between the time this article was written and published, Rachel was hired by CBOBS as a full time 12 month administrator. Congrats Rachel!