Old School Square President and CEO Delray Beach Florida

Old School Square

President and CEO


Old School Square is an award-winning, nationally recognized arts center that has successfully combined historic preservation with the arts to become the catalyst for the 1990s renaissance of downtown Delray Beach. Old School Square upholds the city’s heritage in its three historic buildings while offering a rich variety of concerts, exhibitions, plays, entertainment, and free programming for all ages. Old School Square is truly the cultural hub of its community, serving as a host site for numerous events throughout the year, including the area’s largest First Night celebration, St. Patrick’s Day and Cinco de Mayo commemorations, and multiple food-themed festivals.

The Old School Square campus includes five main facilities: the Cornell Art Museum, Crest Theatre, Fieldhouse, Pavilion, and Creative Arts School. Restored in 1913, the Cornell Art Museum features rotating exhibits of fine art and crafts by regional, national, and international artists. Housed in the restored 1925 Delray High School building, the intimate 323-seat Crest Theatre presents world-class musicals, variety, comedy, film, Broadway cabaret with New York's biggest stars, and lectures with nationally renowned speakers. Formerly known as the Vintage Gymnasium (c. 1925), the Fieldhouse is used for special events, receptions, and private parties. In October 2014 it launched “Catch A Rising Star,” a monthly comedy series.

The Pavilion, which opened in 2002, is a state-of-the-art outdoor performance venue surrounded by an open, grassy area and covered walkway. Free Friday evening concerts at this venue regularly attract thousands of residents and visitors. Lastly, the Creative Arts School offers top-quality photography, art, and writing classes for beginners through master level—building on Old School Square’s commitment to providing learning opportunities for the community. The school also offers a variety of children's classes, art and photography workshops, a Visiting Artist Workshop Series, and Free Open Readings.

Old School Square maintains a close relationship with the City of Delray Beach, which owns the site. The City provides an annual operating grant in addition to maintaining the exteriors and grounds of this historic property. More than 500,000 individuals attend events at Old School Square annually, including 140,000 patrons participating in its self-presented activities. Its current operating budget is $3.3 million, with approximately 35 percent coming from contributed revenues. Old School Square has a 21-member Board of Directors, led by Chair Elise Johnson.


Delray Beach is a first-class resort destination and a diverse, vibrant community situated on the sparkling Atlantic seashore in Palm Beach County, Florida. An intimate yet sophisticated town, Delray Beach began as an agricultural community in 1895 and has become one of Florida's most popular destinations for visitors, new families, and seasonal residents, with its exciting mix of pristine beaches, art, culture, and history. In 2012 Delray Beach was named the most fun small town in the United States by Rand McNally, USA Today, and the Travel Channel on the nationally televised special Best of the Road.

Atlantic Avenue is Delray Beach’s traditional main street. Complete with quaint brick sidewalks, gaslight-style street lamps, gourmet restaurants, outdoor cafes, boutiques, art galleries, and festivals, this downtown area attracts people throughout the year. The arts are never more than a few steps away in Delray Beach. The cultural scene bustles with life in the Pineapple Grove Arts District. Artists Alley is home to arts incubator space Arts Warehouse, art and music venue Arts Garage, more than 20 galleries, and the Spady Cultural Heritage Museum, which tells the rich and diverse history of the Delray community.

Delray Beach encompasses slightly more than 16 square miles, with a growing permanent population of nearly 69,000 residents. Conveniently located just 30 to 45 minutes from both West Palm Beach and Fort Lauderdale International Airports, Delray Beach is only an hour north of Miami. Renewal and redevelopment efforts in Delray Beach have earned the community a coveted All-America City Award by the National Civic League three times. It has also been hailed by city planners around the nation as a model for growth management.

Edited from: visitdelraybeach.org, palmbeachfl.com, mydelraybeach.com, palmbeachculture.com

Position Summary

The President and CEO will have an exciting opportunity to lead the continued growth and evolution of a unique multi-disciplinary, historic cultural center positioned in the heart of Delray Beach’s thriving downtown community. Partnering with a committed board of directors and dedicated senior staff, the President and CEO will assume a highly visible and entrepreneurial role in overseeing all aspects of the organization. This individual will lead the effort to increase both earned and contributed revenue to achieve a long-term, sustainable business model with a focus on philanthropic and sponsorship support.

Acting as the face of the organization, the President and CEO will respect the history and relationships that have sustained Old School Square while bringing a fresh approach to leadership, revenue generation, and community support. The President and CEO will have the ability to address short-term organizational priorities while being mindful of the long-term big picture. Instrumental in strengthening the organization’s essential relationships with the Community Redevelopment Agency and City of Delray local government officials, the President and CEO will play a key role in Old School Square’s strategic initiatives. This individual will also possess the experience, skills, and diplomacy necessary to think strategically, respond to opportunities, and identify relationships and partnerships that will propel Old School Square forward in achieving its mission.

Roles and Responsibilities

Management and Planning

  • Oversee short-term operational and long-range strategic planning and implementation processes, working in close partnership with senior staff.
  • Create a strategic operating plan in conjunction with the senior staff and assume responsibility with the board for its implementation, regularly reporting progress toward goals.
  • Strategize and lead staff toward the implementation of all artistic, educational, and outreach objectives and develop appropriate budgets that fulfill the organization’s artistic and community-based vision and maximize potential revenue.
  • Oversee administrative personnel relations to ensure the organization is effectively structured and staffed with competent employees.

Fundraising and Donor Stewardship

  • Devise, implement, and manage an integrated development program, including the creation of a comprehensive development plan that maximizes contributed income from diverse sources, as principal architect of Old School Square’s fundraising strategy.
  • Assume the lead role in fundraising, working in consultation and cooperation with the board and staff to grow Old School Square’s annual fund, major gift, and sponsorship fundraising by identifying opportunities for new and/or increased support from individuals, foundations, corporations, and government agencies.
  • Implement and promote a planned giving program, informing and educating Old School Square’s constituents about opportunities to support the organization through bequests and legacy gifts that will increase the endowment and help meet future operational needs.
  • Actively guide, educate, and engage the board in fundraising and advocacy with their professional and personal networks and lead staff and volunteers in development activities.

Audience Development and Community Relations

  • Oversee and work closely with marketing staff on all marketing, branding, and public relations programs to achieve earned income goals from performance ticket and event sales and enhance Old School Square’s visibility, reputation, and brand awareness.
  • Ensure the highest levels of customer service, effective audience interaction, and community engagement.
  • Cultivate and sustain positive relations with Delray Beach city leaders and expand outreach to potential strategic partners in the arts, business, government, higher education, and media to advance Old School Square’s institutional reputation and reach.
  • Act as the organization’s principal spokesperson, representing Old School Square in a professional capacity at on-campus events and at numerous other civic and community events and forums.
  • Develop processes for engaging target populations and reaching a broader audience for Old School Square’s multiple performance and event venues and educational programs.

Financial Management and Governance

  • Provide support to best utilize the board’s talents and resources and to stimulate involvement, working closely with them to ensure strong fiscal health and organizational governance.
  • Assume and maintain fiscal oversight of the overall budget and ensure the most effective use of financial resources.
  • Initiate and maintain effective, transparent communication with the Board Chair, board of directors, staff, and volunteers and assist and provide staff support to board committees.
  • Support the board in identifying, cultivating, and recruiting prospective new members to the board.
  • Celebrate the successes of individual board members, and the board as a whole, recognizing their contribution of time and resources to an impactful organization.

Traits and Characteristics

The selected individual will be a persuasive, collaborative leader and a pragmatic visionary who will pursue Old School Square’s goals with optimism and determination, tempered by diplomacy and tact. Along with business acumen, political savvy, and an ability to manage time and priorities, the President and CEO will display a strong patron-focused approach. This individual will also possess superior interpersonal and communication skills and place a high value on building relationships. The President and CEO will maintain an atmosphere in which open communication and stakeholder participation encourage creativity, flexibility, stability, and the achievement of Old School Square’s overall cultural, social, community, and institutional goals.

Other key competencies and motivations include:

  • Leadership – The dexterity to prioritize strategic initiatives while creating a sense of direction embedded in the active participation of a variety of internal and external stakeholders.
  • Collaboration and Accountability – The agility to build diverse and meaningful relationships, listen carefully, and respond conscientiously to an active array of internal and external stakeholders.
  • Customer Focus and Interpersonal Skills – The capacity to exemplify best practices in member satisfaction with a high value on multiple stakeholder needs, to build authentic rapport, and to relate well to a variety of people and experiential perspectives regardless of cultural background.
  • Negotiation, Conflict Management, and Teamwork – The ability to be socially savvy, respectful of differing viewpoints, fair regardless of personal biases, and productive in reaching mutually beneficial outcomes.


A bachelor’s degree is required and a master’s degree in business, arts administration, or related field is highly desirable. At least seven to 10 years of experience in a senior management position at a cultural facility or arts organization serving a variety of user groups is required. Expertise in both development and marketing is preferred. Qualified candidates will have proven success in fund development, external relations, and fiscal management. A demonstrable understanding of programming, facility management and operations, and institutional image building is needed. Knowledge and skillsets that result in the presence and capacity to move initiatives forward in these areas are necessary.

Compensation and Benefits

Competitive compensation and benefits include health/dental plans and a generous vacation policy. Old School Square provides a beautiful and convenient downtown location and the quality of life derived from Delray Beach’s seacoast setting, vibrant cultural life, and year-round sunshine.

Applications and Inquiries

Please submit a cover letter and resume including demonstrable earned and contributed revenue accomplishments (electronic submissions preferred) to:

Ronda Helton, Vice President

Arts Consulting Group

4636 Lebanon Pike, Suite 352
Nashville, TN 37076-1316
Tel       (888) 234.4236 Ext. 218
Email    OldSchoolSquare@ArtsConsulting.com


Old School Square is an equal opportunity employer that
welcomes and values diversity, inclusion, and access in all forms.




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