VP of People & Culture

PINE STREET INN INC • Boston, MA

just now • Onsite

About The Position

The Vice President of People & Culture is a strategic leader responsible for developing and implementing a comprehensive people strategy that emphasizes employee well-being, fairness, and organizational excellence. This role manages the creation, execution, and ongoing enhancement of programs and policies to boost workforce engagement, support professional development and strengthen Pine Street Inn’s reputation as an employer of choice. Primary areas of focus include compensation, advancing employee wellness programs, negotiating and refining benefits packages, optimizing talent acquisition processes, and ensuring a smooth, inclusive onboarding experience for all new employees.

Requirements

• Bachelor’s degree in human resources, Business Administration, or a related field
• Senior-level Human Resources Professional Certification (SPHR, SHRM-SCP)
• Strong organizational and communication skills, including written skills
• Must have an executive mindset to influence and drive internal and external strategy
• Must exercise sound judgment and handle sensitive information with discretion
• Demonstrates critical thinking and independent problem-solving
• Capable of managing a complex workload
• Excellent analytical, interpersonal, and written communication skills
• Able to facilitate, mediate, or lead difficult conversations
• Adaptable to changing priorities
• Show resilience, adaptability, and lead by example
• Committed and passionate about responsibilities
• Maintains confidentiality on sensitive personnel issues

Nice To Haves

• Master's degree in human resources or a related discipline.
• Over a decade of progressive HR experience, including at least five years in senior leadership roles.
• Proven expertise in benefits negotiation, wellness program development, and total rewards strategy.
• Strong background in talent acquisition, onboarding, and employee engagement.
• Excellent interpersonal, negotiation, and communication skills.
• Demonstrated ability to lead with empathy, integrity, and strategic insight.

Responsibilities

• Act as a trusted advisor to the President and Executive Director, Deputy Director, and Chief People and Culture Officer regarding organizational culture, compensation, talent strategy, and workforce planning.
• Develop and lead a comprehensive People & Culture strategy that aligns with Pine Street Inn’s mission, values, and long-term goals.
• Drive initiatives that strengthen a welcoming environment across all levels of the organization.
• Management and supervision of PSI’s compensation programs
• Lead the development and implementation of employee wellness programs supporting physical, mental, and emotional well-being.
• Oversee negotiation and management of employee benefits and compensation, ensuring competitive and cost-effective offerings that support retention and satisfaction.
• Collaborate with finance to monitor benefits utilization and ROI, ensuring alignment with organizational goals and employee needs.
• Advocate a comprehensive “Total Rewards” philosophy that integrates pay transparency, recognition, and professional development opportunities.
• Oversee and enhance recruitment strategies to attract top talent aligned with Pine Street Inn’s mission and values
• Strengthen the employer brand to position the organization as a leader in social impact and workplace excellence.
• Lead the redesign of onboarding and orientation programs to ensure a consistent and engaging experience for new hires.
• Collaborate with hiring managers to create fair and efficient selection processes that support a welcoming environment.
• Foster a culture built on trust, accountability, and ongoing learning.
• Manage regular employee surveys and focus groups to evaluate morale, retention, and the overall workplace environment.
• Champion leadership development and succession planning to build internal capacity and future leaders.
• Support training initiatives that enhance management skills, wellness leadership, and equitable practices.
• Ensure compliance with all federal, state, and local employment laws and regulations.
• Oversee HR policies and conflict resolution processes that promote fairness and transparency.
• Consult with legal counsel as needed on sensitive employment
• Work with Pine Street Inn’s Director of Security to ensure the agency consistently implements PSI's safety and security training, policies, procedures, and monitoring to improve staff safety.
• Participate in management forums, work groups, and meetings as scheduled.
• Lead, communicate, and support management decisions and the Inn’s initiatives, policies, and procedures.
• Performs other related duties as assigned by the Chief of People and Culture Officer.

Benefits

• Employee wellness programs supporting physical, mental, and emotional well-being.
• Competitive and cost-effective offerings that support retention and satisfaction.
• Pay transparency, recognition, and professional development opportunities.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive