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Executive Director- Diamond Head Theatre

Sunday, December 31, 2023

Honolulu, Hawaii, USA


For more than a century, Diamond Head Theatre (DHT), located on the slopes of Diamond Head in Honolulu, Hawaii, has served as Hawaii’s “Broadway of the Pacific”. Opened in 1915, DHT is Hawaii’s oldest performing arts center and the third oldest continuously operating theatre in the entire United States.

On April 28, 1915, a new theatrical group called The Footlights, founded by prominent Honolulu kama’āina (local residents) Will Lewers, Mrs. Walter F. Dillingham, Helen Alexander, Margaret Center and Gerrit Wilder, presented The Amazons by Pinero at the Honolulu Opera House. In 1934, The Footlights reorganized and took on a new name: Honolulu Community Theatre. In the original mission statement, “community service through the art of theatre, involving the people of Hawaii as audience members, stage crew, and performers” is honored and committed to today.

During World War II, Honolulu Community Theatre productions entertained thousands of troops at over 300 performances throughout the Pacific. In 1952, Honolulu Community Theatre took up permanent residence at Ruger Theatre, the aging movie house of army base Fort Ruger. Although never designed for stage productions, the 1930s war-era movie house was retrofitted to include a scene shop and costume center. Lighting and sound systems were installed. A first-ever lobby for their patrons was opened and an upstairs addition for office space, spotlights, and lighting boards were added. In 1990, Honolulu Community Theatre was renamed Diamond Head Theatre. Each season, DHT offers six mainstage theatrical productions, including five major musicals.

Education continues to be fundamental to DHT’s mission. Theatre workshops are provided to train kama’āina in the theatrical arts. A variety of classes including acting, voice and dance classes for keiki (children), teens, and adults are offered throughout the year. The theatre offers an extensive summer school program for keiki and teens and is home to youth performing troupe Diamond Head Theatre Shooting Stars.

The pandemic offered a new perspective for the creative staff of DHT, with drive-in outdoor performances and loyal support from its neighboring community. Conjunctively, in the Fall of 2020, the organization broke ground on a brand-new performing arts complex. The new structure is being built adjacent to the existing theatre, which will allow shows and programs to continue throughout construction. Highlights include the following: a nearly 500-seat auditorium and stage, expanded dressing rooms, orchestra pit, fly loft, additional restrooms, and an expansive outdoor entrance overlooking newly created green space. Other amenities will include an expanded scene shop, loading dock and ultimately, expanded spaces for class offerings, nearly doubling enrollment capacity. A capital campaign continues to support the move into the new state-of-the-art facility slated for a 2023 opening.

As an independent, local, and nonprofit organization led by a versatile and close team comprised of staff and a board of directors, DHT has truly developed into a community center and a gathering place for people of all ages. The theatre community is composed of actors, musicians, production crew members, directors, designers, school groups, educators that are a theatrical ‘ohana. The productions include an all-volunteer cast and crew who celebrate entertainment with the joy of music, song, and dance. Currently the 2021-2022 season includes: Oliver!, Elf, Steel Magnolias, Jesus Christ Superstar, Waitress, and Charlie and the Chocolate Factory.

DHT has a 35+-member board of directors led by Chairman Rick Chong. Executive Director Deena Dray will be retiring from her role in early 2023, after 28 years of service and the substantial completion of a successful capital campaign resulting in the brand-new theatre building. Due to the COVID-19 pandemic, the financials from fiscal year ending June 30, 2019 most accurately represent DHT’s regular operations and are provided here. DHT reported a total revenue of $4.7 million with $3.5 million from contributions and grants, and $943,143 from program services. Total expenses were $2.1 million. 


On the lands of the Kānaka Maoli (Native Hawaiian), Diamond Head (Lē’ahi) sits prominently near the eastern edge of Waikiki’s coastline, as part of Hawaii’s state capital Honolulu. It is home to the saucer-shaped crater that was formed around 300,000 years ago during an explosive volcanic eruption. The Diamond Head-Kapahulu population is 21,079 of the 349,597 living in Honolulu.

Bringing together the beautiful patchwork community of varied diversity, the mo’olelo (stories) of the lands continue to change, evolve, and improve. At Diamond Head Theatre, the spirit of the Hawaiian islands is woven throughout individuals’ lives as it permeates amidst the island. Both integral and connected to Honolulu and geographically separate from the mainland, DHT possesses a culture connected to the United States as a community theatre accessing mainstream entertainment while exuding the aloha culture.

Awareness to the histories of Hawaii and its communication styles are paramount, which DHT holds true to these values. Ideas around the definition of ‘ohana (family) in the artistic sense is important to the DHT community. Decisions are made with an inclusive lens at every level of DHT, and the DHT ‘ohana incorporates an acute perception of listening to the needs of the community and coming together for a common purpose. During the pandemic, DHT maintained its sustainability largely due to this ‘ohana culture and aloha spirit. The community came together, alongside DHT, to understand its fundamental core purpose—entertain through a sense of community togetherness to all it touches.

Within the work culture of DHT, work-life balance is not something just said but lived by. Aligned to the proponents of island time and island culture, what one does for a living professionally is not equivalent to their sense of worth, but how they live outside the walls of their job as well. These values are integrated into every aspect of the DHT community and can be found in everything kama’āina take part.


Position Summary

The Executive Director (ED) at DHT will work to direct and advance all elements of the organization’s mission, strategy, programming, and operations, while honoring the history and work of the organization. Reporting to the Board of Directors and the Executive Committee, the ED will serve as the public face of the organization, and guide both internal and external stakeholders towards a shared vision for DHT. The ED will lead an updated capital campaign under a revised timeline for related projects to the new theatre, scheduled to open in the year 2023. Together with the Board of Directors and its several actively involved committees (including but not limited to the Executive Committee, the Finance Committee, the Governance Committee, the Development Committee, and the Facilities Committee), the ED will co-lead a new strategy, alongside fundraising and community engagement initiatives for DHT to continue its sustainable, community impact. The ED will oversee the Artistic Director, Business Manager, Facilities Committee, Individual and Corporate Gifts Associate, Director of Box Office and Sales, Education Manager and Associate Director of the Shooting Stars, and all contracted staff.

Roles and Responsibilities

Strategic Leadership, Financial Sustainability, and Vision

 Build a deep partnership with the Artistic Director, Board of Directors, and Executive Committee to support the advancement of DHT’s community position, while honoring its legacy and charting a course for a dynamic and inclusive future.

 Facilitate the development of a collaborative vision and strategic plan to advance the mission and broaden DHT’s presence in the community and sector, in partnership with the Board of Directors and Executive Committee.

 Oversee the fiscal responsibility of DHT, monitoring and supporting management of its financial position, multi-year financial goals, seasonal programming, box office and sales, and overall fiscal operation to ensure maximum resource utilization, compliance, and adequate systems of accountability.

 Ensure recruitment and retention of a happy and high functioning team by continuing its welcoming culture of collaboration, developing cohesion alongside the Business Manager through human resource policies and practices, and overseeing a teamwork approach to creative and operations sides.

 Guide the design of the new facility alongside the Board of Directors and Facilities Committee, and serve as a thought partner in the strategic and operational plans for the new facility.

 Collaborate with the Artistic Director on the creative pillar of DHT, while maintaining fiscal integrity to sustain the organization.

Community Relations, Capital Campaign, and Fundraising

 Coordinate and guide a diversified approach on community relations, as well as continue to develop and sustain the community funds and partnerships consistent and authentic to DHT’s brand and messaging framework in collaboration with the Board of Directors and contracted staff.

 Advocate for DHT as a visible and inspiring spokesperson who promotes inclusivity of the Diamond Head communities, including funders, donors, sponsors, civic leaders, community partners, and subscribers as well as organizations across Honolulu, the islands of Hawaii, and on the mainland.

 Engage key stakeholders actively and strategically to form and deepen relationships, steward strategic alliances, and maintain strong partnerships with regional civic, business, and philanthropic leaders.

 Create and pursue contributed revenue goals, including the current capital campaign, donor campaigns, major gifts, sponsorships, fundraising events, grants, and other development efforts that increase the number of supporters and depth of support in partnership with the team, Artistic Director, and development staff.

 Develop and adopt creative goals and initiatives that study and expand the size, scale, and diversity of participation across audience, education, and community programs with the Education Manager & Associate, Director of the Shooting Stars, the Director of Special Projects, and key staff.

 Engineer strategies in fundraising, resource development, marketing, and communications to significantly enhance revenues and create a wider base of support that builds upon the loyal financial foundation within the organization.

Board Governance and Organizational Management

 Inspire effective working relationships with and among the board and the Executive Committee to encourage active participation and ambassadorship in the community.

 Communicate with the board in a timely and accurate manner, all information necessary for the board to function properly and to make informed decisions related to each individual’s areas of responsibility.

 Ensure strong fiscal health, thoughtful succession planning, and good governance with the Board of Directors.

 Lead the administration of DHT’s day-to-day operations and hiring and managing staff, while directing all administrative areas, including Development, Finance, Human Resources, and Marketing and all programming areas, including Education, Shooting Stars, and Special Projects.

 Serve as DHT’s primary negotiator and signatory, ensuring ethical and responsible practices in due diligence, acquisition, and management of all contracts, including grants, labor relations, real estate, professional services, consultants, and other vendors.

 Empower the management team to work effectively across departments towards shared goals and objectives that are clear, consistent, and measurable.


Traits and Characteristics

The Executive Director will be dynamic, inspiring, confident, and a supportive leader who will communicate directly with tact, respect, and appreciation, while serving as a representative and spokesperson for the organization. Experienced and successful in working in a collaborative model, this passionate individual will strive for management excellence within a small team and a myriad of volunteers, and organizational success committed to nurturing a positive workplace environment consistent with the aloha culture.

An advocate and leader for the arts, the ED will work to bridge the new and old eras of voices and perspectives inside the organization and across the community, crafting an integrated framework for sustainability and advancement. They will bring a familiarity and/or curiosity for the diverse cultures found in the communities of Honolulu, and they will be gifted in maintaining and diversifying funding and other forms of partnership and support. The ideal leader will understand how to partner effectively in a collaborative model that involves drive, innovation, and motivation, as well as humility, support, and honesty. The ED will build genuine relationships with all stakeholders, both internal and external, and advance the values of equity, diversity, and inclusion in all management decisions.

Other key competencies include:

 Interpersonal Skills and Customer Focus – The ability to effectively communicate, building rapport and relating well to all kinds of people, as well as anticipating, meeting and/or exceeding customer and stakeholder needs, wants, and expectations.

 Diplomacy and Personal Accountability – The capacity to handle difficult or sensitive issues effectively and tactfully, while being answerable for personal actions. The ability to be honest, communicate directly while still maintaining a sense of respect.

 Leadership and Teamwork – The dexterity to organize and influence people to believe in a vision while creating a sense of purpose and direction, while cooperating with others to meet objectives. The ability to be consistent and supportive. A guide and thought partner, as well as a creator of purpose-driven systems.

 Time and Priority Management – The acuity to prioritize and complete tasks to deliver desired outcomes within allotted time frames.


No specific equivalent educational credentials or number of years’ experience are required. The ED will have a strong understanding of nonprofit fundraising, theatre, and educational programming, coupled with kama’āina culture in collaboration with its diverse creative and operational teams. Strong business experience, as well as with a deep interest and background in both the performing arts and aloha culture, are welcomed. Exceptional writing abilities and verbal presentation skills are expected.

Compensation and Benefits

DHT provides a competitive and equitable compensation package with a salary in the range of $85,000 to $125,000 depending on experience. Benefits include paid vacation, sick leave, personal days, and holidays; health insurance with full coverage paid, long-term disability, term life, and accidental death insurance; a dental plan; and a 403(b)-retirement plan with company match. A relocation bonus will be offered to the placed candidate, if not based locally.

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