Executive Director, Four Winds * Westward Ho

Orcas Island, WA | Year-Round

$150,000 to $175,000 plus benefits and year-round housing

The incoming Executive Director will transition into the role following the summer 2027 season, allowing time for a thoughtful handoff.

Background

About Four Winds * Westward Ho

Four Winds * Westward Ho is an independent, nonprofit residential summer camp on Orcas Island in Washington State's San Juan Islands. Founded in 1927, Four Winds has a rich legacy with traditions that span generations. The camp’s values of community, simplicity, and creativity are threaded through every aspect of camp life, from vintage uniforms, music, arts, and hand-carved signs to singing and reciting poetry by the fireside. Four Winds * Westward Ho proudly became a nonprofit in the 1960s and established a tuition assistance program in the 1980s.

Four Winds is home to ~350 campers each summer ages 9-15 who attend one of the two four-week sessions offered. Campers develop skills in sailing, horseback riding, arts and crafts, music, singing, sports, and tending to the camp garden. Senior campers embark on a six-day trip throughout the San Juan Islands by vintage war canoe, kayak, or sail boat, with an additional backpacking trip to the Olympic National Park. The Big Boat sailing has been a tradition from the founding of Four Winds. Aboard the 62-foot Carlyn, senior campers embark on a three-week sailing voyage into Canadian waters. The boat is used throughout the summer for shorter trips exploring the local waters of the Salish Sea.

Our Home on Orcas Island

Nestled in a private harbor, Four Winds sits on 150 acres of waterfront property on traditional homeland and waterways of the Coast Salish people on Orcas Island. Orcas is one of the four main islands in the San Juan archipelago served by Washington State Ferries. A scenic ferry ride of a little over an hour connects the island to Anacortes, which is 90 minutes north of Seattle. The island is also accessible by commercial flights and seaplanes. Orcas Island is home to about 6,000 year-round residents, with many more maintaining second homes on the island. It has a strong public school system and two independent schools on the island. Eastsound is the largest town with a library, bustling shops, and a vibrant restaurant scene.

Four Winds was established on the western part of the island, in the hamlet of Deer Harbor on West Sound. From the rocky shores of Breakfast Beach to the moss-covered stones on Hill of the Moon to the afternoon light across the horse pastures, it is truly a majestic place. Anyone who has spent time at camp understands immediately why generations are drawn to Four Winds. The next leader will be a steward of this cherished place and a leader to a community of thousands.

The property has a private director’s home suitable for year-round family use. Past directors have lived onsite and the Board’s strong preference is that the next leader will call Orcas Island home year-round. For an exceptional candidate, there may be flexibility to live off island during the off-season and at camp during the spring and summer months.

Position Overview

Reporting to the Board of Directors, the Executive Director (ED) serves as the strategic and community leader of Four Winds, guiding its year-round and summer community with vision, passion, and care, while honoring camp's cherished traditions.

The Executive Director will be supported by a Camp Director who will lead the day-to-day summer program. With a valued summer leader in place, the ED's primary responsibilities will be to implement the camp's long-term strategic plan, build strong Board partnerships, ensure the financial health of the organization, and develop a high-performing team of camp professionals. The ED will also lead fundraising and donor development, as well as build out new revenue streams that extend Four Winds' impact beyond the summer season. In addition, this role partners with the Board to establish meaningful community partnerships in support of the tuition assistance program. The ED is expected to be a positive presence at camp during the summer and engage in the Orcas Island community throughout the year.

The incoming Executive Director will transition into the role following the summer 2027 season, allowing time for a thoughtful handoff.

Compensation is $150,000 to $175,000 plus benefits and year-round housing at camp.

Year-Round Leadership Team

The Executive Director will oversee a year-round staff of 8 to 10 people. Direct reports include:

Camp Director: Manages all summer programming, seasonal staff hiring and supervision, and the full summer operation.
Facilities Director: Oversees the property and buildings year-round.
Development Director: Leads fundraising, donor relations, and alumni engagement.
Director of Family Experience: Manages camper enrollment, parent communication, and marketing.

Other members of the year-round team include a Program Director, Boatwright, and Captain of the Carlyn sailboat.

Responsibilities

People Leadership

Lead, support, and manage the year-round team with clear expectations, regular feedback, and investment in each person's professional growth.
Maintain the healthy internal culture of accountability rooted in camp's mission and values.
Support the Camp Director in building out a strong summer leadership structure and managing camp programming.

Development, Financial Oversight, and Operations

Lead the organization's fundraising strategy in partnership with the Development Director, with a goal of raising at least $500K annually.
Serve as the primary face of Four Winds with donors and alumni, personally cultivating relationships with supporters and identifying new donors with significant giving capacity.
Lead capital campaign planning and execution in partnership with the Board.
Oversee budgeting, financial reporting, and fiscal health with the Finance Committee.
Build systems and controls to manage operational activities, including HR, payroll, vendor management, safety, compliance, and insurance.
Develop and maintain a proactive risk management plan covering physical, operational, and geographic risks. Build strong relationships with local emergency services and the Orcas Island community to support emergency preparedness.
Plan capital needs of the property and facility; work with the Board to design and budget for new, improved, or enhanced buildings and grounds.

Enrollment & Camper Recruitment

Support the Director of Family Experience and Camp Director in maintaining a robust enrollment pipeline and achieving maximum camper capacity.
Partner with the Camp Director and program team to evaluate and evolve camp programs to provide differentiated experiences that meet today's camper expectations and honor Four Winds traditions.

Off-Season Revenue Development

Take ownership of building a sustainable off-season revenue strategy that is consistent with the camp's values and mission. Identify new opportunities to generate revenue and enable summer tuition to be more accessible.

Identify, pilot, and grow revenue programs such as educational partnerships, sailing excursions aboard the Carlyn, and artist residencies aligned with Four Winds' creative traditions.
Build relationships with local vendors, hospitality partners, and event planners on Orcas Island to support program execution.
Establish pricing, policies, and operational protocols that protect the property and align with the camp's values and insurance requirements.

Board Partnership & Governance

Partner with the Board to execute long-range planning and governance, leveraging their expertise as strategic partners.
Provide proactive, regular, and transparent updates on the organization's health, including financials, enrollment, staffing, safety, and challenges that require Board guidance.

Qualifications

5+ years experience in a leadership position at a camp or educational setting.
Demonstrated track record managing teams, budgets, and organizational priorities.
Experience in a nonprofit setting working with a volunteer Board of Directors.
Demonstrated entrepreneurial mindset with experience identifying and developing new revenue opportunities preferred.
Experience with event programming and property rentals is a plus.
Ability to live onsite at camp on Orcas Island or in Western Washington year-round.
Ability to travel periodically throughout the West Coast for community events and to attend camp conferences.
Flexibility to work irregular hours.
Familiarity with camp management systems preferred.
Comfort navigating camp's varied terrain, including walking trails, docks, and waterfront areas, as well as occasional lifting and physical tasks.

Compensation & Benefits

Compensation is $150,000 to $175,000 with benefits, paid time off, and flexible off-season hours. Onsite housing is available year-round, and meals are provided during camp months. Full benefits include:

Silver health insurance plan with 100% of employee premiums and 80% of dependent premiums covered by the employer
Dental and vision insurance with 80% of employee premiums and 50% of dependent premiums covered by the employer
Tax-advantaged Health Care Flexible Spending Account (FSA) with an employer contribution of $500 to $1,500, based on the employee’s elected contribution
SIMPLE IRA with a 4% employer match

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Executive Director, Four Winds * Westward Ho