Chief People Officer

Job DescriptionChief 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, Chief Philanthropy Officer, Chief Marketing Officer, and Associate Artistic Director.Reports to: Executive and Artistic DirectorStatus: Full-time, year-round, exemptDirect Reports: Talent, Inclusion & Culture Director; Special Projects Manager; Office Administrator / Alumni Coordinator; Wellness ConsultantKey Partners: Chief Financial Officer; Chief Philanthropy Officer; Chief Marketing Officer; Associate Artistic Director; Board of Trustees Executive CommitteePeople and Culture LeadershipLead all aspects of the People and Culture function, including employee relations, talent acquisition, professional development, compensation and benefits, performance management, HR systems, 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 the function's workings, expectations, and support access.Provide thought partnership on organizational design, role clarity, and team structure as the organization evolves.Oversee the summer festival Wellness Program.Lead the design and administration of annual and periodic staff surveys, establishing success metrics for people and culture goals.Key Priorities for the First Two to Three YearsBuild 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 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 exacerbate.Employee Relations and Culture BuildingBring a sophisticated, mediator's sensibility to conflict resolution and employee relations matters, handling sensitive situations with discretion, fairness, and care.Support a culture rooted in respect, transparency, and accountability, aligned with the organization's values.Build trust through consistency, follow-through, and genuine accessibility to staff at every level.Anticipate issues before they arise and apply a proactive, human-centered approach to staff support, including across the dynamics of full-time, seasonal, intern, and contractor staff.Model the kind of healthy, sustainable working rhythms the organization seeks to cultivate organization-wide.Operations, Accountability, Policy and ComplianceStrengthen and refine HR systems, policies, and procedures, building on the foundation of existing SOP, handbook, and policy infrastructure.Implement sharp accountability practices across the people-and-finance interface, including timekeeping, expense reconciliation, survey responses, and related responsibilities.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.Leverage legal fluency in employment matters and a network or capacity to engage outside counsel when necessary.Talent Acquisition, Onboarding, and DevelopmentLead recruitment strategy and practice across the organization, ensuring equitable job descriptions, salaries, and processes aligned with strategic goals.Strengthen onboarding and orientation for the annual cohort of approximately 20 interns and 60 seasonal staff members.Build management training and coaching offerings, focusing on conflict resolution, feedback, and supervisory practice.Enhance the capabilities of supervisors and people managers, equipping them with tools, frameworks, and ongoing support to lead teams effectively and navigate people decisions.Lead professional development and retention strategies, including stay and exit interviews and translating staff feedback into action.Support comprehensive diversity within the organization, including at the Director level.Multi-Generational Workforce and EngagementPrioritize support and development of early-career staff, building practices that meet emerging professionals while maintaining clear expectations and standards.Apply fluency in the realities of a multi-generational workforce, addressing communication styles, feedback expectations, and mental health and well‐being.Offer 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, engaging the IDEA Steering Committee and partnering with senior leadership on strategy.Raise awareness and sensitivity to issues of inclusion, diversity, equity, and access, contributing to systems evolution within the broader arts ecology.Cross-Functional PartnershipCollaborate closely with the Chief Financial Officer on payroll, benefits, compensation strategy, and the people-related dimensions of strategic and budgetary planning.Oversee all internal communications among staff and 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 people practices align with festival, school, and year-round programming realities.Partner with marketing and communications leadership to align internal culture with external brand promise, ensuring staff experience informs audience experience.Contribute to a cohesive senior leadership team and provide regular reporting to the Executive Committee of the Board of Trustees.CompensationThe 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; a Health Reimbursement Arrangement; pre-tax Flexible Spending Accounts; life insurance; short- and long-term disability; an Employee Assistance Program; and travel assistance. Time off includes paid vacation, holidays, sick leave, and Massachusetts Paid Family & Medical Leave through a private plan with Unum. Retirement benefits include a 403(b) plan with a 2% employer contribution. 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.RequirementsExperience and QualificationsDemonstrated senior leadership experience in People and Culture or Human Resources, with a track record of operational discipline and authentic people acumen in a mission-driven organization.Demonstrated history leading a busy departmental team.Cultural literacy is essential; backgrounds considered include nonprofit, higher education, arts, and cultural institutions. Performing arts experience is preferred but not required.Advanced conflict resolution and mediation skills; ability to navigate complex interpersonal and organizational dynamics.Strong understanding of employment law and compliance; experience overseeing HR systems and operations; ability to engage legal counsel as needed.Experience building or strengthening HR systems, policies, and operational infrastructure in organizations with complex or seasonal staffing patterns.Proven partnership with finance leadership on operational and strategic dimensions of people work.Track record of supervising, mentoring, and supporting emerging professionals, with fluency in a multi-generational workforce.Dedication to inclusion, diversity, equity, and access, with the ability to translate that commitment into practice at individual and institutional levels.Proficiency with various technologies, including AI, to support workforce efficiency.Capacity to build trust with a board of trustees and communicate clearly and credibly at the executive level.The Successful Candidate Will BringA deeply human-centered approach respecting individuals and creative work.Exceptional communication skills grounded in empathy and compassion; steadiness to make difficult decisions and enforce policies consistently.Strong, visible presence and the ability to communicate clearly with leadership, staff, and trustees.Emotional intelligence, patience, sound judgment, and calm, thoughtful decision-making in complex moments.Operational rigor and an instinct for sharpening accountability practices while maintaining warmth and trust.A collaborative mindset, working in partnership with all senior leaders and stakeholders.Balance compassion with accountability, offering warmth and support while making thoughtful decisions in service of the organization.Connection to mission-driven work and appreciation for the creative process and culture's role in artistic excellence.Commitment to modeling sustainable, healthy working practices for an organization demanding a great deal of its people, especially during Festival season.Commitment to consistency and stability, building sustained confidence in People and Culture through reliability, follow-through, and forward momentum.Application InstructionsThe Chief People Officer search is being conducted on behalf of Jacob's Pillow by TOC Arts Partners, led by Edie Demas. To apply, 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 not evident in your résumé. Applications will be accepted until the role is filled.#J-18808-Ljbffr