About the Opportunity
This is a unique opportunity to join one of the nation’s leading cultural institutions at a moment of meaningful transition and renewal. The Director of People & Culture will lead a team with the goal to help stabilize, strengthen, and reimagine the employee experience, supporting both the people and the art at the heart of the organization. The Director of People & Culture will serve as a key member of the senior leadership team, responsible for shaping and stewarding a people-centered culture within a highly collaborative and uniquely complex theatrical environment.
This is a pivotal moment for the Oregon Shakespeare Festival. Following a period of leadership transition, evolving labor dynamics, and recovery from the pandemic closures, the Festival is experiencing an exciting time of revival. Audiences are growing; critical reception for the work is thriving; and the artistic vision for the future of the company is expansive and inclusive. The Director of People & Culture will play a central role in strengthening internal systems and fostering a cohesive and supportive workplace culture at a time when the impact of their work will be pivotal to the continuing success of the organization. This is both a stabilization and an impact opportunity—requiring a leader who can balance empathy with rigor, listening with action, and relationship-building with operational discipline.
About the Oregon Shakespeare Festival
The Oregon Shakespeare Festival (OSF) was founded in 1935 in Ashland, OR, and has grown from a three-day festival of two plays to a nationally renowned theatre arts organization that presents a rotating repertory season of up to 10 plays and musicals, including illuminating interpretations of Shakespeare, other enduring classics, and new works. OSF productions have been presented on Broadway, internationally, and at regional, community, and high school theatres across the country. OSF received the 1983 Special Tony Award for Outstanding Regional Theatre and is one of the largest nonprofit theatres in the nation with three stages, including an outdoor Allen Elizabethan Theatre.
The Oregon Shakespeare Festival creates world-class theatre, revealing our collective humanity through illuminating interpretations of new and classic plays, and inspiring a love of our art form for current and future generations. Under the leadership of Artistic Director Tim Bond and acting Executive Director Javier Dubon, a team of over 500 theater professionals produce thrilling theatrical experiences to audiences of over 130,000 from every state in the U.S.
Learn more about the Festival: www.osfashland.org
About Ashland, Oregon
Nestled in the Rogue Valley of southern Oregon, where the Cascades meet the Siskiyou Mountains, Ashland is a beautifully unique town, in a beautifully unique setting. The small town atmosphere of Ashland (population 21,000) holds many surprises for first time visitors – this small community has the rich cultural life of a city many times its size, with a varied artistic community including and beyond the Festival; a culinary scene that includes world class chefs and home grown cooking stars; access to nature that is literally at one’s doorstep; a nationally recognized wine growing region and industry; and an engaged and active local population. The Festival’s impact on the town, the presence of Southern Oregon University, and the thriving tourism industry has helped build a population of both residents and visitors who represent a wealth of backgrounds, education, and life experiences that gives Ashland its vibrancy. It is a town that is self-reflective in grappling with both its history and its future, and invites involvement from all who choose to call it home. Located roughly equidistant between San Francisco and Portland for weekend road trips, and with an airport in nearby Medford that makes travel out of the valley easy, Ashland offers the experience of small town life with great convenience to travel when desired.
Learn more about Ashland and Oregon:
www.travelashland.com
www.ashlandchamber.com
www.traveloregon.com
Job Description
The Director of People & Culture will be a visible, trusted, and relationship-driven leader, responsible for fostering a people-centered culture within a highly collaborative and uniquely complex theatrical environment. This individual will play a critical role in building trust, strengthening communication, and supporting a healthy, connected workplace, bringing a leadership approach grounded in empathy, transparency, and sound judgment.
Key Responsibilities
People & Culture Leadership
- Lead all aspects of People & Culture, including employee relations, professional development, recruitment, compensation, benefits, and compliance
- Serve as a trusted advisor to senior leadership on organizational health, culture, and people strategy
- Foster a workplace culture rooted in respect, inclusion, transparency, and accountability
Employee Relations & Culture Building
- Provide thoughtful, human-centered guidance on employee relations matters
- Help build trust through fairness, consistency, and clear communication
- Support a culture where staff feel heard, valued, and supported
Labor Relations
- Lead and support collective bargaining and union relationships across multiple bargaining units
- Navigate ongoing labor dynamics with skill, credibility, and respect
- Ensure compliance with applicable labor laws, with particular attention to Oregon-specific requirements
Operations & Infrastructure
- Strengthen and streamline HR systems, policies, and procedures
- Improve onboarding, offboarding, and overall employee experience
- Ensure operational excellence while adapting systems to a complex, non-linear environment
Manager & Leadership Support
- Provide guidance and training to managers to strengthen leadership capacity across the organization
- Help clarify roles, expectations, and processes to reduce administrative burden
- Support a more consistent and effective approach to people management
Cross-Functional Collaboration
- Partner closely with Finance on payroll, benefits, and strategic planning budgetary needs
- Collaborate with Artistic and Production leadership to ensure alignment with the realities of the needs of theatrical operations
- Contribute to a cohesive and aligned senior leadership team
Key Priorities
- Strengthen employee relations practices, ensuring a human-centered, fair, and responsive approach to staff support
- Stabilize and enhance core HR systems and processes, including onboarding, offboarding, and policy clarity
- Support and guide managers across the organization, through consistent, transparent, and accessible practices
- Navigate and strengthen labor relations within a highly unionized environment, helping to strengthen productive relationships with union partners
- Improve communication and cohesion across a large and physically dispersed organization
- Establish strong cross-functional partnerships, particularly with finance and senior leadership, to ensure alignment and shared decision-making
- Provide proactive leadership, anticipating organizational needs and helping to mitigate challenges before they escalate
Experience & Qualifications
- Demonstrated leadership experience in People & Culture / Human Resources, ideally in a complex, mission-driven organization
- Experience in the performing arts, theatre, or similarly collaborative creative environments strongly preferred
- Deep knowledge of labor relations and collective bargaining, ideally within unionized environments
- Strong understanding of employment law and compliance, including Oregon-specific requirements
- Experience building or strengthening HR systems, policies, and operational infrastructure
- Proven ability to navigate complexity, balance competing priorities, and work across diverse stakeholder groups
- Track record of building trust and strengthening organizational culture
The successful candidate will bring:
- A deeply human-centered approach, leading with empathy, compassion, and respect for the individuals and creative work that define the organization
- A strong, visible presence, building trust through accessibility, consistency, and authentic relationship-building across all levels of the company
- Emotional intelligence and steadiness, with the ability to navigate complex interpersonal dynamics with patience, good judgment, and a calm, thoughtful approach
- Humility and low ego, demonstrating openness, curiosity, and a willingness to listen and learn while fostering a culture of mutual respect
- A collaborative mindset, working in close partnership with leadership and staff, valuing shared ownership, and engaging stakeholders in decision-making
- Clear and transparent communication, providing context, rationale, and follow-through to build understanding and confidence across the organization
- The ability to balance compassion with accountability, offering warmth and support while making thoughtful, sometimes difficult decisions in service of the organization
- A genuine connection to the mission and art form, with an appreciation for the creative process and the role culture plays in supporting artistic work
- A commitment to consistency and stability, helping to build confidence in People & Culture through reliability, follow-through, and sustained engagement
Compensation
The salary for this position is $135,000 – 155,000.
The Oregon Shakespeare Festival provides comprehensive benefits, including providing Medical, Dental, and Vision coverage, flexible spending account options, an Employee Assistance Program; Free/Discounted Show Tickets; local discounts, and Group and Voluntary Life Insurance
Application Instructions
The Director of People & Culture search is being conducted on behalf of the Oregon Shakespeare Festival by TOC Arts Partners, a national consultancy aligning strategies, structures, and leadership toward a thriving cultural sector. The search is being led by VP of Executive Search Cynthia Fuhrman, in consultation with and support from the TOC Arts Partners search team.
To apply, visit the online application and submit your materials. Your cover letter should include any training or experience relevant to the job profile that you would like to highlight, why you consider yourself a good fit for this opportunity, and anything else you’d like us to know about your qualifications that may not be present in your resume. Applications will be accepted until this role is filled.
For general questions or nominations of prospective candidates, please contact searchteam@tocartspartners.com. We kindly request no phone calls.
Specific questions about the position may be directed to:
Cynthia Fuhrman
VP, Executive Search
cynthia@tocartspartners.com
Not sure you meet 100% of our qualifications? Research shows that cis men apply for jobs when they fulfill an average of 60% of the criteria, while others tend only to apply if they meet every requirement. If you believe that you could excel in this role, we encourage you to apply. We are dedicated to considering a broad array of candidates, including those with diverse workplace experiences and backgrounds. So, whether you’re returning to work after a gap in employment, simply looking to transition, or taking the next step in your career path, we will be glad to have you on our radar.
