President and CEO, Old School Square

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President and CEO, Old School Square


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.


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