People & Culture Manager (Seasonal)

POSITION OVERVIEW

Jacob’s Pillow is in a period of growth and organizational evolution within its People & Culture function. To ensure continuity, operational excellence, and high-quality support for our staff during this transition, we are seeking a People & Culture Manager (Temporary) to join our team on a temporary basis, starting as soon as possible through December 2026.

This is a hands-on, high-impact role embedded within a small, dynamic People & Culture team. You will report to the Director of Talent, Inclusion & Culture and work alongside a People Operations Manager and an Office Administrator & Alumni Relations Coordinator. The ideal candidate thrives in fast-paced, mission-driven environments and brings both strategic thinking and a roll-up-your-sleeves operational approach to HR work.

This role is hybrid, with required on-site presence during the summer festival season (approximately June through August). Candidates who are local to western Massachusetts or reside within a one-hour radius of Becket, MA are strongly preferred.

RESPONSIBILITIES

Key Responsibilities

Employee Relations & Staff Engagement

• Serve as a trusted resource and first point of contact for employee relations matters, including workplace concerns, conflict resolution, and performance-related conversations.
• Conduct fair, thorough, and timely investigations when needed, ensuring compliance with organizational policy and applicable employment law.
• Coach managers and supervisors on best practices for feedback, documentation, and navigating sensitive personnel situations.
• Partner with leadership to proactively identify and address workplace climate issues before they escalate.
• Support the planning and execution of staff events, social programming, and community-building activities that foster connection and belonging across year-round and seasonal staff.
• Design and implement engagement initiatives that strengthen staff morale, retention, and sense of belonging.

Affinity Groups & Employee Resource Groups (ERGs)

• Provide operational and strategic support to existing and emerging Affinity Groups and ERGs, including meeting facilitation, resource coordination, and leadership development for group leads.
• Collaborate with the Director of Talent, Inclusion & Culture to align ERG programming with the organization’s broader inclusion and belonging strategy.
• Serve as an accessible liaison between ERG members and organizational leadership, ensuring that employee voices inform institutional decision-making.

Leave Management, Workers’ Compensation & Compliance

• Serve as a primary liaison for all employee leave programs, including FMLA, PFML, ADA accommodations, and other statutory and organizational leave policies, coordinating intake, documentation, and return-to-work processes in partnership with the Director of Talent, Inclusion & Culture.
• Provide end-to-end operational support for workers’ compensation claims, coordinating with carriers, healthcare providers, and supervisors to ensure timely reporting, proper documentation, and compliance. Serve as a key liaison to the People Operations Manager, taking temporary ownership of the process and providing critical capacity during high-volume periods.
• Own the I-9 verification process for all new hires under the guidance of the People Operations Manager, ensuring compliance with federal employment eligibility requirements and maintaining audit-ready records.
• Support compliance with federal, state, and local wage-and-hour regulations, benefits reporting requirements, and ACA obligations.

Payroll & Benefits Support

• Provide high-level support to the People Operations Manager, who leads payroll processing, by assisting with troubleshooting, auditing timekeeping records, and resolving discrepancies within the organization’s HRIS (Paycom).
• Serve as a knowledgeable resource for staff on benefits enrollment, eligibility, claims issues, and life-event changes, working directly with carriers and vendors as needed.
• Collaborate with the People Operations Manager to maintain data integrity across payroll, benefits, and personnel systems.

People & Culture Operations & SOPs

• Support the development, updating, and maintenance of departmental Standard Operating Procedures (SOPs) to ensure consistency, compliance, and institutional knowledge continuity.
• Contribute to department-wide projects and priorities as they emerge during the transition period, including policy updates, process improvements, and documentation.
• Maintain strict confidentiality and exercise sound judgment in all matters related to personnel information and organizational operations.
• Support the transition to incoming permanent leadership by ensuring clean documentation, organized systems, and a clear operational handoff.

QUALIFICATIONS

Required

• +5 years of progressive HR/People Operations experience, with demonstrated depth in employee relations, leave management, and payroll/benefits support.
• Strong working knowledge of federal and Massachusetts employment law, including FMLA, PFML, ADA, wage-and-hour, workers’ compensation, and benefits compliance.
• Hands-on experience with HRIS platforms (Paycom experience strongly preferred) and comfort navigating payroll and benefits systems at a detailed, transactional level.
• Experience managing I-9 verification processes and maintaining compliant employment eligibility records.
• Excellent interpersonal and communication skills, with the ability to build trust quickly across all levels of an organization.
• Proven ability to handle sensitive situations with discretion, empathy, and a commitment to fairness.
• Experience working in mission-driven, nonprofit, or arts/cultural organizations.

Preferred

• PHR, SPHR, SHRM-CP, or SHRM-SCP certification.
• Experience supporting or facilitating Affinity Groups, ERGs, or DEIB programming.
• Familiarity with the unique HR dynamics of organizations with both year-round and large-scale seasonal workforces.
• Comfort operating with a high degree of autonomy in a small-team environment.
• Experience developing, writing, or maintaining HR Standard Operating Procedures.
• Local to western Massachusetts or within a one-hour commuting radius of Becket, MA.

PHYSICAL DEMANDS & WORK ENVIRONMENT

• Work environment includes both indoor office and outdoor campus settings; summer months involve increased activity, foot traffic, and pace.
• Occasional evening or weekend work may be required during Festival and programming periods.
• Working regularly in wooded areas and uneven terrain with exposure to native wildlife, including, but not limited to, rodents, ticks, and mosquitos.
• Working regularly outdoors in all weather conditions, including inclement weather.
• Moving through and between multiple locations throughout the entire campus.
• Remaining in a stationary position for extended periods of time.

• We believe that no one meets 100% of the listed qualifications. We are less concerned about whether you’ve done everything on a laundry list of specific things and more interested in cultivating a pool of candidates who want to join a connected, mission-driven, hard-working team driven by creativity, curiosity, inclusion, integrity, flexibility, and partnership.

HIRING PROCESS

• Apply: Interested individuals are encouraged to send a cover letter, resume, and references by submitting an application using the “Apply” buttons below. Video and/or audio applications are welcome (though not required) in addition to written expressions of interest.
• Interview: Pre-Screening on Zoom, Hiring Manager Interview on Zoom, In-Person Interview with Panel, Hiring Manager, and Tour of Grounds.
• Supplemental Materials: A writing sample, spreadsheet example, or other relevant materials may be requested from candidates should they be a top candidates.

If you need accommodations to make this application process happen, please connect with us at people@jacobspillow.org. We will work to support you through the application process via email, phone call, and/or video chat.