Associate Director Opening

Four Winds * Westward Ho is seeking its next Associate Director. This is an incredible leadership opportunity at an incredible camp, and we’re seeking a truly special camp professional. If you understand deeply what a traditional Camp experience can do for young people, are willing to do what it takes to make that experience the best it can be, understand the challenges of running a camp in 2024, and can bring your talents to bear on that task, then you should give this position a look.

Ruth Brown, a former schoolteacher, founded Four Winds in 1927. In 1968, Miss Ruth retired, created a 501(c)3 organization, and donated Four Winds to that organization. So, for the second half of its life, Four Winds has appeared on the surface to be just like some of the best privately owned camps in the country, but with the advantages of running as a nonprofit organization. Because of our nonprofit status, we’ve created and maintained one of the country’s most robust financial aid programs, reserving 20% of our camper spots for families that need financial aid, despite having a long waitlist of families willing to pay full price. We’ve been able to maintain our unique tradition of big boat sailing, owning and operating a 61’ yawl, Carlyn. And, we’ve been able to maintain the magical (though somewhat high maintenance) character of our beautiful 160-acre property on Orcas Island.

But, all of that is secondary to the community we create for young people in the summer. For almost 100 years, this place has provided the most valuable and positive formative experiences in the lives of thousands of children. The Associate Director is a key part of making that happen every summer.



  • In concert with the Assistant and Executive Director, recruit, select, and onboard 100 summer staff. Manage all postings across a variety of job search networks, and update job descriptions as necessary.
  • With the Assistant and Executive Director, travel during most of January and February to promote Four Winds through slideshow presentations, engaging with current and prospective families and alumni. This position will coordinate travel schedules and liaise with host families. 
  • Attend professional development events, often requiring travel.
  • With the Assistant Director, plan a two-week summer staff training period, designing and updating curriculum annually, and managing flow.
  • Promote Four Winds: Write articles, web copy, and social media posts. Create slideshows of camp photography designed to showcase our mission, place, and values.
  • Handle in-advance summer logistics including but not limited to: Summer staff paperwork, summer staff logistics, assisting with camper transportation, and scheduling.
  • Participate actively in the improvement of our programs and systems.
  • Assist in the coordination of off-season events such as Board Meetings, Reunions, and any other community effort as needed.

In summer:

  • With the Assistant and Executive Director, execute a two-week staff training period, including leading staff training sessions.
  • With the Assistant and Executive Director, support and supervise seasonal management team of 12, who in turn supervise the rest of the summer staff.
  • Act as direct supervisor to the Heads of Sides (head counselors) and Heads of Leadership Training Programs. 
  • Coordinate logistics – travel, trips, activities, schedules. 
  • Interact with parents/guardians – there are plenty of casual interactions when it’s important to be a good ambassador for camp, but the crux of this aspect of the job is the Associate Director is one of our key people who talk with parents/guardians when there’s a challenge of some sort with their camper.
  •  Solve problems. Assist summer staff in solving whatever problems may arise.
  • Be an impeccable role model for campers and staff.
  •  Do what needs to be done in order to give the campers the summer of their lives. Sometimes this involves mentoring a camper or counselor who’s struggling. Sometimes this involves plunging a toilet.
  • Work long hours in the summer. A normal day in summer is 14 hours, and 16 or 18 happens all the time. We shoot for 6-8 days off over the course of summer, plus about 2 evenings off a week, but we’re on call 24 hours a day. This is what is expected of counselors and other summer staff, and there’s no way to lead them without living the same schedule they do. 


  • In the event of the absence or incapacitation of the Executive Director, serve as Acting Executive Director until the ED can return, or if the ED cannot return, until the Board of Trustees can fill the role.


  • Strong leadership, meaning the willingness and ability to influence others’ behavior in a way that brings us closer to the ideal Camp experience.
  • Previous year round program focused leadership at a summer camp or similar program is desired. At least three seasons in a leadership role at a summer camp or similar outdoor education program is required. Preference will be given to candidates who have taken on roles of increased responsibility and work at programs that are more similar to Four Winds than not.
  • Organizational Skills – The candidate must keep dozens of facts and tasks straight at a given time, without dropping balls.
  • Flexibility – Every day is different at Camp, and the candidate will need to be able to change gears.
  • Empathy – Camp can be an emotionally intense place, and the ability to understand how others are feeling is a key leadership quality.
  • Trust – the ability to build and maintain trust with a diverse group of people. 
  • The ability to communicate well and professionally in diverse and sometimes difficult circumstances, maintaining confidentiality when needed.
  • Excellent writing skills.
  • Computer savvy.
  • A Bachelor’s degree or equivalent.
  • At least 21 years old (an insurance requirement to drive Camp-owned vehicles).
  • Eligible to work in the United States
  • Valid Driver’s license and clean driving record.
  • Ability to pass a criminal background check.
  • The ability to walk over rough terrain at least 3 miles a day.
  • CPR, First Aid, Washington State Food Handler’s, and Washington State Boater Education certifications, or the ability to obtain those certifications.


  • The salary range for this position will be $75,000-$100,000 annually. To be at the higher end of this range, previous year-round employment at a summer camp or similar program is required. 
  • This position will require living on the Four Winds property in the summer, and housing is provided at no cost to the employee. Family members of the successful candidate are welcome to live in the provided housing as well, in accordance with our Guidelines for Residents of Four Winds. Housing options range from a studio apartment to a small two-bedroom home, and will be assigned based on the successful candidate’s needs as well as those of other employees. It is an option for this position to live on the property year-round, but remote work arrangements will also be an option for the off-season.
  • This is a year-round, full-time, FLSA Exempt position.
  • Benefits include:
    • Paid Time Off (two weeks vacation, increasing to three weeks after three years, and four weeks after six years, 13 paid holidays, including the week between Christmas and New Year’s Day, and up to four weeks of sick time).
    • a Health Reimbursement Arrangement benefit of $950/month
    • a SIMPLE-IRA retirement plan including employer match of employees’ contributions up to 3% of the employee’s salary.

To apply:

Send an email with a resume and cover letter attached in pdf format to Preference will given to candidates who submit resumes before January 7, 2024. Please do not send hard copies. Phone interviews will begin with selected candidates as soon as is practicable, with in-person interviews to follow for the candidates that move on from the phone interview round. Start date is as soon as possible, with preference given to candidates that can start earlier. The latest possible start date for the position is April, 2024.

Four Winds is an equal opportunity employer. People of all backgrounds are encouraged to apply.