Chief People Officer - Jacob’s Pillow via TOC Arts Partners

Chief People Officer
Position Profile

About the Opportunity

Jacob's Pillow has spent more than 90 years building one of the world's most distinctive and beloved performing arts institutions, a place where the art form of dance is presented, studied, celebrated, and preserved. Under Executive and Artistic Director Pamela Tatge's leadership since 2016, the organization has grown significantly. The year-round staff has grown from 36 to 53 people, the budget has expanded in kind, and the reach of Jacob’s Pillow has extended well beyond its Berkshires home through online programming, international partnerships, and a major new investment in its digital platform through the Bloomberg Digital Accelerator. The completion of the new Doris Duke Theatre’s construction in 2025 stands as a marker of both institutional confidence and the remarkable generosity of the community that embraces “the Pillow.”

That growth has also created new demands. A team of 50-plus (that grows to 130 staff in the summer with seasonal staff)  is a fundamentally different organization than a team of 30, and a year-round institution is a fundamentally different culture than a summer festival. The Pillow is now closing out its current five-year strategic plan and preparing for the next one, and the leadership structure is evolving to meet the moment. Adding a Chief People Officer (CPO) to the senior team is a clear signal that people, their development, their wellbeing, and the culture they share, are a strategic priority and central to how the organization operates.

This is a meaningful distinction. Our Talent, Inclusion & Culture Director manages the HR function, including policies, compliance, and day-to-day operations. The Chief People Officer will shape the environment in which the work happens. Sitting at the senior leadership table, the CPO will bring a people lens to organizational decisions before those decisions are made, and take responsibility for culture as an ongoing, intentional practice. At an organization navigating the shift from summer festival to year-round institution, with a largely early-career staff, that distinction matters enormously. 

Jacob's Pillow seeks a Chief People Officer to serve as a senior leader and trusted partner to Executive and Artistic Director Pamela Tatge and the senior leadership team. The CPO will bring sophisticated operational discipline together with genuine, finely tuned people acumen, guiding all aspects of the employee experience across a workforce that includes full-time staff, seasonal employees, interns, students, contractors, and visiting artists. The successful candidate will need to bring exceptional communication skills rooted in empathy and compassion, alongside the resolve to make and enforce difficult decisions. This is a role for a leader who can hold both rigor and care, who builds infrastructure that scales, and who is known for steady, fair, and thoughtful judgment in moments that matter.

The organization has invested meaningfully in building out its people and culture function over the last several years, including the development of comprehensive policies, an updated handbook, and a culture statement co-created with staff. The CPO will inherit that foundation and bring fresh eyes and continued forward momentum, helping to evolve the structure of People and Culture, support managers across departments, and build a workplace where staff at every level, and at every life stage, feel cared for and equipped to do their best work. The board has expressed clear enthusiasm for the leadership the CPO will bring to the organization.

The Pillow's campus, its 10-week summer Festival, and its year-round programming create a uniquely complex environment. Staff live and work in close proximity during the season; the pace is fast; the stakes are high; and the people involved range from students and emerging artists to longtime trustees and internationally celebrated dance companies. The CPO will be at home in that complexity and will model the kind of healthy, sustainable, and human-centered leadership the organization wants to see at every level.

This role requires genuine presence. The Berkshires are a destination, and the work of building culture happens in person and year-round. The right candidate will be based locally or willing to relocate, and will show up as a consistent, trusted presence for a staff that spans archive and production, facilities and fundraising, the year-round core, and the seasonal surge that defines festival life each summer.

About Jacob’s Pillow

Jacob’s Pillow, a National Historic Landmark and recipient of the National Medal of Arts, is a year-round center for dance and home to America’s longest-running international dance festival, located in the Berkshires of Western Massachusetts. The Pillow encompasses the world-renowned Jacob’s Pillow Dance Festival, presenting more than 40 dance companies and over 350 events each summer; The School at Jacob’s Pillow, one of the most prestigious pre-professional dance training centers in the U.S.; the Pillow Lab, a residency program supporting new choreography; growing Community Engagement programs serving local school children, artists, and community members; rare and extensive dance Archives, open to the public, that chronicle more than a century of dance through photographs, performance videos, talks with artists, costumes, and scholarly essays; a robust online platform that provides audiences all over the world with access to the Archives, regular livestreams and encore presentations available on demand and an Internship Program that provides professional advancement and training opportunities.

The Pillow’s mission is to support dance creation, presentation, education, and preservation, and to engage and deepen public appreciation and support for dance. Jacob’s Pillow is committed to providing an inclusive, diverse, accessible, and equitable environment that cultivates the celebration of the art of dance and its positive impact on communities. Organization-wide values include inclusion, leadership, integrity, flexibility, partnership, and sustainability. The organization’s culture statement, developed with staff, reflects shared commitments to people-centered care, mutual support, adaptability, continuous learning, and shared purpose.

About the Berkshires

The Berkshires, located in Western Massachusetts and roughly equidistant from Boston and New York City, is a thriving cultural, and primarily rural region filled with historic landmarks, museums, and performing arts venues, with a mix of year-round and seasonal residents. The Pillow’s campus sits within easy reach of a vibrant ecosystem of arts and cultural organizations, including Tanglewood, MASS MoCA, the Clark Art Institute, Barrington Stage, and Shakespeare & Company.

The Chief People Officer may be based in the Berkshires or in another location accessible within an hour. During the summer Festival season (mid-June through late August), when the organization is fully staffed with seasonal staff and interns and is operating at its highest pace and volume, on-site presence is essential. In the off-season, a hybrid work schedule is possible.

Job Description

The Chief People Officer is a visible, trusted, and relationship-driven leader, responsible for shaping a people-centered culture within a highly collaborative and uniquely complex performing arts environment. The CPO partners closely with the Executive and Artistic Director and serves as a peer to the Chief Financial Officer (a role created at the same time, and currently being recruited) as well as the Chief Philanthropy Officer, Chief Marketing Officer, and Associate Artistic Director, ensuring that the organization’s commitments to its people are reflected in clear policy, sound process, and consistent day-to-day practice. The CPO works closely with department heads to support the workforce throughout the employee lifecycle, with particular attention to the dynamics between full-time, seasonal, intern, and contracted staff, and the realities of an organization where many employees live on campus during the Festival.

Reports to: Executive and Artistic Director
Status: Full-time, year-round, exempt
Direct Reports: Talent, Inclusion & Culture Director, Special Projects Manager; Office Administrator / Alumni Coordinator, Wellness Consultant
Key Partners: Leadership Team that includes: Chief Financial Officer; Chief Philanthropy Officer, Chief Marketing Officer, and Associate Artistic Director; Board of Trustees Executive Committee

People and Culture Leadership

• Lead all aspects of the People and Culture function, including employee relations, talent acquisition, professional development, compensation and benefits, performance management, HR systems and operations, and compliance
• Serve as a trusted advisor to the Executive and Artistic Director and senior leadership team on organizational health, culture, and people strategy
• Continue to evolve the structure of the People and Culture function, communicating clearly with staff about how the function works, what staff can expect, and how to access support
• Provide thought partnership on organizational design, role clarity, and team structure as the organization continues to evolve
• Oversee the summer festival Wellness Program
• Lead the design and administration of annual and periodic staff surveys, and establish the success metrics that determine how the organization knows it is making progress on its people and culture goals.

Key Priorities for the First Two to Three Years

• Build continuity and stabilize a new way of working for the team, supporting the ongoing evolution of the People and Culture function with clarity and consistent communication
• Strengthen accountability infrastructure across the people-and-finance interface, sharpening the operational disciplines that support a well-run organization
• Deepen support and development for early-career staff as a defined organizational priority
• Build a strong, peer-level partnership with the Leadership Team
  Support managers across the organization through coaching, training, and accessible practices that strengthen leadership capacity
• Continue IDEA commitments through the lens of People and Culture practice
• Provide proactive, anticipatory leadership, helping to mitigate organizational challenges before they escalate

Employee Relations and Culture Building

• Bring a sophisticated, mediator’s sensibility to conflict resolution and employee relations matters, with the experience and judgment to handle sensitive situations with discretion, fairness, and care
• Support a culture rooted in respect, transparency, and accountability, in alignment with the values articulated in the Pillow’s culture statement
• Build trust through consistency, follow-through, and genuine accessibility to staff at every level
• Anticipate issues before they escalate and bring a proactive, human-centered approach to staff support, including across the dynamics that arise between full-time, seasonal, intern, and contracted staff
• Model the kind of healthy, sustainable working rhythms the Pillow seeks to cultivate organization-wide

Operations, Accountability, Policy and Compliance

• Strengthen and refine HR systems, policies, and procedures, building on the comprehensive SOP, handbook, and policy infrastructure already in place
• Bring sharp accountability practices to operational disciplines that span the people-and-finance interface, including timekeeping, expense reconciliation, response to staff surveys, and similar accountabilities that support a well-run organization
• Maintain personnel policy, employee records, and required reporting in accordance with federal and Massachusetts state laws
• Ensure compliance across all phases of the employee lifecycle, including non-profit hiring practices, employment law, payroll integrity, and benefits administration
• Bring legal fluency in employment matters and a network or capacity to engage outside counsel when needed

Talent Acquisition, Onboarding, and Development

• Lead recruitment strategy and practice across the organization, working with hiring managers to ensure job descriptions, salaries, and processes are equitable and aligned with strategic goals
• Strengthen onboarding and orientation, including for the annual cohort of approximately 20 interns and 60 seasonal staff members
• Build management training and coaching offerings, with particular focus on conflict resolution, feedback, and supervisory practice
• Strengthen the capabilities of supervisors and people managers across the organization, equipping them with the tools, frameworks, and ongoing support needed to lead teams effectively, develop their staff, and navigate day-to-day people decisions with confidence
• Lead professional development and retention strategies, including stay and exit interviews and the translation of staff feedback into action
• Support comprehensive diversity within the organization, including at the Director level

Multi-Generational Workforce and Engagement

• Prioritize the support and development of early-career staff, building practices that meet emerging professionals where they are while maintaining clear expectations and standards
• Bring fluency in the realities of a multi-generational workforce, including communication styles, feedback expectations, and approaches to mental health and wellbeing
• Provide thoughtful guidance on the unique dynamics that arise when staff live on campus together for ten weeks, balancing care with appropriate professional structure

Inclusion, Diversity, Equity, and Access (IDEA)

• Serve as an active partner in the organization’s ongoing commitments to IDEA, including engagement with the staff IDEA Steering Committee and partnership with senior leadership on strategy
• Bring awareness and sensitivity to issues of inclusion, diversity, equity, and access, and a desire to contribute to systems evolution in the broader arts ecology

Cross-Functional Partnership

• Partner closely with the Chief Financial Officer on payroll, benefits, compensation strategy, and the people-related dimensions of strategic and budgetary planning, identifying efficiencies and opportunities at the people-finance interface
• Oversee all internal communications among staff. Partner with the Associate Artistic Director on cross-departmental collaboration, supported by the Strategic Projects Manager
• Collaborate with artistic, production, education, hospitality, and operations leadership to ensure that people practices align with the realities of festival, school, and year-round programming
• Partner with marketing and communications leadership to ensure  the Pillow's internal culture is a living embodiment of its external brand promise, recognizing that staff experience shapes audience experience, that artists and visitors feel the culture of the place from the moment they arrive, and that authentic alignment between how the organization speaks about itself and how it operates internally is among its most powerful reputational assets
• Contribute to a cohesive senior leadership team and provide regular reporting to the Executive Committee of the Board of Trustees

Experience and Qualifications

• Demonstrated senior leadership experience in People and Culture or Human Resources, with a track record of bringing both operational discipline and authentic people acumen to a complex, mission-driven organization
• Demonstrated history leading a busy departmental team 
• Cultural literacy is essential. The Pillow welcomes candidates from a wide range of professional backgrounds, including nonprofit organizations with year-round and seasonal workforces, higher education, broader arts and cultural institutions, and other mission-driven environments. Performing arts experience is preferred but not required
• Sophisticated skill in conflict resolution and mediation, with the experience and judgment to navigate complex interpersonal and organizational dynamics
• Strong understanding of employment law and compliance, with experience overseeing HR systems and operations and the ability to engage legal counsel effectively when needed
• Experience building or strengthening HR systems, policies, and operational infrastructure in organizations with complex or seasonal staffing patterns
• Proven ability to partner effectively with finance leadership on the operational and strategic dimensions of people work
• Track record of supervising, mentoring, and supporting emerging professionals, with fluency in the dynamics of a multi-generational workforce
• Demonstrated commitment to inclusion, diversity, equity, and access, with experience translating that commitment into practice at both the individual and institutional level
• Experience with various technologies, inclusive of AI, to support a workforce and potentially contribute to efficiencies of scale
• Ability to build trust with a board of trustees and to communicate clearly and credibly at the executive level

The Successful Candidate Will Bring

• A deeply human-centered approach and respect for the individuals and creative work that define the organization
• Exceptional communication skills grounded in empathy and compassion, paired with the judgment and steadiness to make difficult decisions and enforce policies consistently, even when doing so is uncomfortable
• A strong, visible presence and the ability to communicate clearly with leadership, staff, and trustees alike, providing context, rationale, and follow-through
• Emotional intelligence and steadiness, with patience, sound judgment, and a calm, thoughtful approach in complex moments
• Operational rigor and an instinct for sharpening accountability practices without sacrificing warmth or trust
• A collaborative mindset, working in close partnership with the Executive and Artistic Director, the CFO, senior leaders, staff, and engaging stakeholders in shared decision-making
• 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 mission-driven work, with appreciation for the creative process and the role culture plays in supporting artistic excellence
• A commitment to modeling sustainable, healthy working practices for an organization that asks a great deal of its people, particularly during the Festival season
• A commitment to consistency and stability, helping to build sustained confidence in People and Culture through reliability, follow-through, and steady forward momentum

Compensation

The salary range for this position is $155,000 to $175,000, commensurate with experience. Jacob’s Pillow offers a generous benefits package including medical, dental, and vision insurance through Blue Cross Blue Shield of MA, Delta Dental, and VSP, with coverage beginning day one of employment, plus an employer-funded Health Reimbursement Arrangement (HRA) that covers the majority of the medical deductible. Employees can also enroll in pre-tax Flexible Spending Accounts for medical and dependent care. Life insurance and AD&D (up to 3x salary), short- and long-term disability, the Employee Assistance Program, and travel assistance are all 100% employer-paid. Time off includes paid vacation, holidays, and sick leave, alongside Massachusetts Paid Family & Medical Leave through a private plan with Unum. For retirement, we offer a 403(b) plan with a 2% employer contribution toward annual salary. On campus during the Summer Festival season, employees enjoy three free meals a day, complimentary tickets to performances, and access to Pillow programs and archives.

Application Instructions

The Chief People Officer search is being conducted on behalf of Jacob’s Pillow by TOC Arts Partners, a national consultancy aligning strategies, structures, and leadership toward a thriving cultural sector. The search is being led by Edie Demas.

To apply, please submit your materials through the online application. Your cover letter should include any training or experience relevant to the position profile that you would like to highlight, why you consider yourself a strong fit for this opportunity, and anything else you would like us to know about your qualifications that may not be evident in your resume. Applications will be accepted until the role is filled.

For general questions or to nominate a prospective candidate, please contact searchteam@tocartspartners.com. We kindly request no phone calls.

Specific questions about the position may be directed to:
Edie Demas
TOC Arts Partners
edie@tocartspartners.com

Not sure you meet 100% of our qualifications? Research shows that some candidates apply for jobs when they fulfill an average of 60% of the criteria, while others tend to apply only 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. Whether you are returning to work after a gap in employment, looking to transition, or taking the next step in your career path, we will be glad to have you on our radar.

Jacob’s Pillow is a registered 501(c)(3) not-for-profit organization that provides equal opportunity for all employees and applicants for employment without regard to race, color, creed, religion, gender, sexual orientation, national origin, age, marital status, mental or physical disability, pregnancy, military or veteran status, or any other basis prohibited by state or federal law.