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Pine Street Inn

VP of People & Culture

Posted 2 Days Ago
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In-Office
Boston, MA, USA
Expert/Leader
In-Office
Boston, MA, USA
Expert/Leader
Strategic HR leader responsible for developing and executing people and culture strategy, including compensation, benefits, wellness, talent acquisition, onboarding, employee engagement, leadership development, compliance, and workforce planning. Oversees an 11-person department, advises executive leadership, negotiates benefits, measures KPIs (retention, wellness participation, time-to-fill), and ensures equitable, legally compliant HR policies and practices.
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Description

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.

Key Responsibilities, And Essential Duties 

• 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 

Employee Wellness & Total Rewards

• 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.

Talent Acquisition & Onboarding

• 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.

Culture And Employee Engagement

• 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.

Talent Development 

• 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.

Compliance And Risk Management

• 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

Requirements

Required Education / Professional Qualifications:

- Bachelor’s degree in human resources, Business Administration, or a related field

• Senior-level Human Resources Professional Certification (SPHR, SHRM-SCP)

Preferred:

• 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.

Key Performance Indicators (KPI's)

The following key performance indicators will measure success in this role:

• Increased employee wellness participation and satisfaction scores year over year.

• Improved retention rates and decreased turnover in key departments.

• Successful negotiation of benefits programs that effectively balance cost and employee satisfaction.

• Enhanced time-to-fill and quality-of-hire metrics across all departments.

• New hire onboarding satisfaction and engagement scores surpassing 85%.

• Engage in market data analysis annually to ensure compensation is competitive.

REQUIRED PHYSICAL ABILITIES/SKILLS:

• Requires prolonged sitting and the ability to operate computers and other office equipment.

• Also, must be able to access various locations at Pine Street Inn and elsewhere.

REQUIRED MENTAL ABILITIES/SKILLS: 

• 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

WORKING CONDITIONS:

Additional time beyond the basic schedule as necessary to fulfill job requirements

Regulatory Safety and Security

• 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.

The Duties:

• 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.

SUPERVISION TO BE EXERCISED: Oversees an 11-member department directly or indirectly. Director-level 

positions:

o 2 Director-level positions

o 1 Manager level positions 

o 5 Recruiters

o 2 Benefits Coordinators

o 1 HR support staff

Pine Street Inn Boston, Massachusetts, USA Office

444 Harrison Avenue, Boston, MA, United States, 02118

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