Chief People Officer: Culture & Growth

Cathleen Stone Island

Boston (MA)

Hybrid

USD 130,000 - 145,000

Full time

3 days ago

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Benefits offered by this job

Medical insurance with employer 80%

Dental, vision, FSA, life, disability

401(k) with employer match

Generous PTO: 17 vac, 20 personal, 13f

Job summary

Cathleen Stone Island Outward Bound School (CSIOBS) in Boston seeks a Senior Director of Human Resources to lead all aspects of people strategy, culture, and operations. This role partners with the CEO and senior leadership to drive talent, engagement, and compliance in a dynamic, events-driven environment.

The ideal candidate has extensive HR leadership experience, nonprofit expertise, and a commitment to youth development.

Qualifications

Minimum 5 years of progressive HR leadership experience including senior-level responsibility.
Supervisory experience and building an HR team preferred.
Strong working knowledge of employment law, compliance, and best practices.
Proven ability to lead with empathy, discretion, and sound judgment.
Nonprofit, education, youth-serving, outdoor education, healthcare, or human services experience strongly preferred.
Background check required for this position.

Responsibilities

Serve as a strategic partner to the CEO and senior leadership team.
Lead evolution and scaling of the HR function balancing compliance, care, and accountability.
Establish clear goals, benchmarks, and performance indicators for HR success.
Build the systems, discipline, and culture to support growth, staff development, and retention.
Utilize people systems and data to inform strategic decision-making and forecasting.
Provide regular reporting on workforce trends, turnover, engagement, and compliance.
Oversee benefits administration and payroll processing coordination.