Executive Director

Full time / $275,000-$325,000 annually / Oregon Shakespeare Festival / Ashland, OR

The Executive Director will be responsible for leading the business operations of OSF with a particular focus on financial management, contributed revenue growth, audience development, and general administration. Reporting to the Board of Directors in a co-leadership model with the Artistic Director, they will collaborate with all departments to ensure a culture of transparency, trust, and high performance. As a visible advocate for OSF and the arts both regionally and nationally, the Executive Director will engage and embrace the Ashland community by listening actively to constituents while deepening and forming new partnerships with donors, businesses, civic leaders, and other stakeholders. Envisioning and charting a new strategic future for the organization in conjunction with the Artistic Director and Board, the Executive Director will ensure its continued growth, relevance, and sustainability in a rapidly evolving cultural landscape. A fearless champion of IDEA work, they will ensure that all artistic and administrative decisions are made in alignment with OSF’s mission, vision, and values.

Roles and Responsibilities
Financial Leadership and Revenue Generation
• Develop and implement comprehensive financial strategies to ensure the organization’s sustainability and growth, aligning them with organizational goals and objectives.
• Monitor financial performance in collaboration with the senior leadership team through budget development and management, maximizing revenues, controlling expenses, and overseeing financial processes for decision-making and long-term fiscal health.
• Oversee the preparation of and present detailed financial reports to the Board of Directors while conducting forecasting and analysis with the senior leadership team to optimize revenue generation and audience participation.
• Enhance fundraising efforts through cultivating and maintaining relationships with individual donors, foundations, corporate sponsors, and government agencies.
• Lead strategies to identify, cultivate, and secure major gifts in collaboration with the Chief Development Officer, Artistic Director, and Board of Directors.
• Increase earned revenue through innovative ticket sales and other revenue generating strategies while ensuring positive and memorable audience experience facilitated by the Box Office, Front of House, Concessions, Gift Shop, and Volunteer Coordination functions.
• Embrace other financial leadership and revenue generation responsibilities, as needed.

Strategic Vision and Relationship Building
• Partner with the Artistic Director to support and implement OSF’s artistic vision and financial sustainability creating and implementing a long-term and compelling strategic plan which is in alignment with the organizational mission and values.
• Identify emerging industry trends and opportunities to inform strategic decision-making and envision a new future for the organization and the multiple types of communities it serves.
• Engage and embrace the local and national community as a public spokesperson and ambassador, raising awareness and support for the organization’s activities, while creating opportunities for collaboration with the City of Ashland, Chamber of Commerce, City of Medford, Jackson County, and other community partners.
• Cultivate strategic partnerships with other arts organizations, businesses, educational institutions, and civic groups to expand the reach and impact of OSF within the community and well beyond.
• Champion IDEA initiatives and strategies to foster an inclusive and welcoming environment for all staff, artists, audiences, and community members that also attract and engage new and diverse global audiences.
• Embrace other strategic vision and relationship responsibilities, as needed.

Organizational Leadership and Operational Excellence
• Develop and maintain a consistent system of human resources support and practices, creating a space and place of belonging for all employees and audiences through concrete actions and systemic improvements.
• Inspire leadership and provide direction to staff and recruit, develop, and retain top talent while empowering them to excel in their roles.
• Ensure a secure, consistent, and reliable technology systems infrastructure, including personal productivity units, servers, networks, and applications.
• Manage the portfolio of owned and rented properties, including their insurance, maintenance, leasing and security, while protecting OSF’s interests with consistent contracting practices and workflows.
• Provide an industry leading visiting company member experience, through company housing, transportation, and hospitality.
• Develop and implement comprehensive emergency preparedness plans to address the ongoing environmental risks caused by climate change, fires, and smoke.
• Plan and facilitate engagement and ensure regular and transparent communication with the Board and Board Committees for oversight, governance, and strategic benefit, and provide assistance to the OSF Endowment Board of Trustees, as needed.
• Embrace other organizational leadership and operational excellence responsibilities, as needed.

Traits and Characteristics
The Executive Director will be an inspiring and strategic visionary who is action oriented in leading with a collaborative approach to decision making. Emotionally intelligent, authentic, approachable, and humble, they will be a good listener and a transparent communicator who takes satisfaction in seeing others achieve their best intellectually, emotionally, and artistically. Resilient and decisive, the Executive Director will be adept at working in a fast-paced, sometimes ambiguous environment while maintaining a stabilizing and optimistic outlook when faced with a variety of challenges. As an ambassador for OSF, the Executive Director will champion its mission, vision, and values while exemplifying a dedication to fostering an inclusive culture and welcoming destination.

Other key competencies include:

• Personal Accountability and Diplomacy — The ability to demonstrate responsibility for personal and professional actions while adeptly managing challenging or delicate situations with tact and discretion.
• Leadership and Flexibility — The capacity to mobilize and inspire others around a shared vision while fostering a clear sense of purpose and direction while regularly adapting approaches as circumstances change.
• Time and Priority Management, and Planning and Organizing — The dexterity to prioritize and complete tasks skillfully within specified timeframes along with establishing courses of action to ensure efficient and effective means to achieve goals and objectives.

• Interpersonal skills — The acuity to effectively communicate, build connections, and foster positive relationships with individuals from diverse social, cultural, socioeconomic, and other backgrounds.

Compensation and Benefits
OSF provides a competitive and equitable compensation package in the range of $275,000 to $325,000 with benefits that include paid time off and holidays; health insurance (medical, dental, vision); long-term disability and life insurances; and an employer contributed 403(b) retirement plan.

Requirements

A bachelor’s degree is expected and an advanced degree in arts administration, business, or a related field is preferred. The ideal candidate will have a track record of leadership experience within complex and dynamic nonprofit arts organizations, businesses, or creative industries of significant size and scope. Demonstrable achievements in financial management, fundraising, marketing, and developing actionable strategic plans are required. A familiarity with and understanding of southern Oregon and cultural destination branding and marketing are very helpful and collective bargaining experience is advantageous. A passion for arts education and community engagement is expected with proven expertise in spearheading inclusion, diversity, equity, and accessibility initiatives. Exceptional written and verbal communication skills are critical.