Senior Director of Human Resources

Cathleen Stone Island; Boston (MA); Hybrid; USD 130,000 - 145,000; Full time

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.

Skills

HR leadership

Employment law

Strategic partnership

Data-driven HR

Tools

Paylocity

Job description

Change, Culture and Engagement Department

Classification: Exempt (Salaried)
Status: Full-Time
Salary Range: $130,000 – $145,000
Location: 21 Drydock Ave, Suite 320W, Boston, MA (with required work on Cathleen Stone Island, Boston Harbor)
Reports to: CEO & President

Cathleen Stone Island Outward Bound School (CSIOBS) is a Boston-based nonprofit organization that partners with Boston Public Schools to provide, experiential learning programs that build academic success, social-emotional skills, and leadership capacity in young people. Rooted in the Outward Bound educational philosophy of learning through challenge and discovery, CSIOBS programs integrate hands-on STEM learning, outdoor adventure, and character development.

ABOUT THE OPPORTUNITY

Nestled in Boston’s vibrant Seaport District, Cathleen Stone Island Outward Bound School (CSIOBS) stands as one of the city’s most enduring youth development organizations. Each year, we empower students from Boston Public Schools while proudly belonging to the Outward Bound USA federation. We are embarking on an exciting new chapter as we are launching the first phase of our ambitious five-year strategic plan.

This Senior Human Resources leadership role blends big-picture strategy with hands-on action. Known internally as Change, Culture & Engagement (CCE), our department supports a dedicated team of about 70 year-round staff, swelling to nearly 150 during our busiest seasons. The unique island setting, ferry commutes, and lively calendar of events make CSIOBS a dynamic workplace that calls for agile, inspiring leadership.

The Senior Director of Human Resources (SDHR) will shape every facet of the employee journey, from talent strategy and recruitment to performance, culture, and well-being. Collaborating closely with the CEO and President, and senior leaders, the SDHR will help foster a thriving, inclusive organization deeply committed to youth development and the energy of our events-driven location.

The SDHR will inspire a dedicated team that champions educators, program staff, operations, hospitality, advancement, and administration. By shaping people policies, nurturing employee relations, and ensuring fair pay and benefits, this leader builds a workplace where positivity, safety, and fulfillment thrive.

As CSIOBS expands its reach as a nonprofit, this role becomes the linchpin that unites our staff, systems, and culture to advance our mission, deliver outstanding programs, and secure a vibrant future.

WHAT SUCCESS LOOKS LIKE IN YEAR ONE

• This is an opportunity to design and build a team with skills, capabilities and competencies that will help to build a strong foundation.
• Strong HR background with a foundation of policies, processes and systems that are utilized by leaders and employees at large.
• Strong, trusted partnership with the CEO & President and senior leadership team.
• Effective and consistent people systems across hiring, onboarding, performance, and engagement.
• Improved clarity, accountability, and confidence among managers.
• Reliable People & Culture metrics and reporting to inform decision-making.
• A positive and supported employee experience across roles and programs.

ESSENTIAL FUNCTIONS

Strategic People & Culture Leadership

• Serve as a strategic partner to the CEO & President and senior leadership team, contributing to organization-wide strategy beyond people operations.
• Lead the evolution and scaling of the HR function that balances compliance, care, and accountability.
• Establish clear goals, benchmarks, and performance indicators for HR success; adapt strategy based on results and learning.
• Build the systems, discipline, and culture necessary to support organizational growth, staff development, and retention.
• Utilize People systems and data to inform strategic decision‑making, planning, and forecasting.
• Provide regular reporting on workforce trends, turnover, engagement, and compliance.

Talent Acquisition, Development & Performance Management

• Lead full‑cycle recruitment efforts for year‑round, seasonal, and program‑based staff, including employer branding and hiring manager partnership.
• Design and oversee onboarding processes that set staff up for success and reinforce organizational values.
• Manage and continuously improve performance management processes, including goal setting, check‑ins, evaluations, and performance increases.
• Support leadership development, succession planning, and staff training initiatives.

Employee Relations & Organizational Culture

• Serve as the primary advisor to managers and leadership on employee relations, performance issues, and workplace investigations.
• Foster a culture rooted in trust, inclusion, transparency, and accountability.
• Lead employee engagement efforts and continuous improvement of the overall employee experience.
• Reach out to the contracted employment attorney for expert guidance whenever the situation calls for it.
• Conduct and analyze exit interviews and employee feedback to inform retention strategies.
• Ensure compliance with all applicable federal, state, and local employment laws and regulations.
• Oversee workers’ compensation, ADA accommodations, and all employee leave processes, including FMLA and MA PFML.
• Ensure completion of required audits and reporting deadlines.
• Maintain data integrity and confidentiality of personnel records.
• Oversee CORI, SORI, fingerprinting, background checks, and safeguarding requirements for youth-serving organizations.
• Work with the Chief of Staff, as a member of the OBUSA HR Group, to ensure CSIOBS complies with the OBUSA National Operating Standards.

Compensation, Benefits & People Operations

• Oversee benefits administration and serve as liaison with brokers and providers.
• Lead annual open enrollment, including planning, communication, and administration.
• Ensure People systems accurately reflect compensation, benefits, time tracking, and leave balances.
• Manage the People & Culture budget, vendors, and external partners.
• Oversee accurate and timely payroll processing in coordination with internal and external partners.
• Manage the HRIS system through optimization and efficiency. (Paylocity) Leverage AI and ensure alignment with the operation.

QUALIFICATIONS

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

WORK ENVIRONMENT

• This role operates in a hybrid work environment that includes time in a professional office setting and on‑site work on Cathleen Stone Island in Boston Harbor.
• On‑island work is required periodically April through October, and in‑person engagement is a core expectation of this position.
• The position requires frequent collaboration with colleagues across Programs, Operations, Safety, and Advancement, as well as participation in meetings and organizational events. Standard office equipment and technology are used regularly, and occasional evening or weekend work is expected.

PHYSICAL DEMANDS

• This position is primarily sedentary and involves working at a computer and participating in meetings.
• The role requires the ability to move around office, school, and outdoor spaces, travel to off‑site meetings, and navigate the island campus, including walking on uneven surfaces.
• Periodic travel via ferry to and from Cathleen Stone Island is required.
• Minimal lifting is expected, and reasonable accommodation may be made.

TRAVEL REQUIREMENTS

This position requires local travel primarily within the Greater Boston area, including regular visits to Cathleen Stone Island. Ferry transportation to the island is provided by the organization.

OUR BENEFITS

• We are committed to staff learning, growth, and development. Our holistic investment includes:
• Medical insurance with up to 80% employer contribution Dental, vision, FSA, life, and disability insurance plans 401(K) and Employer Match Generous paid time off, including 17 vacation days, 20 personal days, and 13 company‑wide holidays.
• Individual, local, regional, and national training opportunities
• A commitment to developing leaders within the organization
• An organizational culture that supports staff well‑being and holistic self-care
• Ample opportunities to connect with the students and communities we serve

OUR COMMITMENT TO EQUITY, DIVERSITY, INCLUSION, AND BELONGING

Our staff and board care deeply about social justice, equity, and diverse perspectives and backgrounds, creating a rich environment and strengthening our ability to pursue our mission. We are committed to fostering a workplace where people of all backgrounds are welcomed, valued, and supported.

EQUAL OPPORTUNITY EMPLOYER

CSIOBS is an equal opportunity employer and actively seeks staff who reflect the diversity of the communities we serve. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability status, protected veteran status, or any other characteristic protected by law.

CSIOBS has a zero‑tolerance policy for incidents of child abuse and neglect. Protecting our minor students against abuse and neglect is of the highest priority.