Chief of Staff
About The Position
The Chief of Staff serves as the CEO’s principal operational and strategic partner, responsible for translating organizational strategy into execution across all administrative and operational functions. The Chief of Staff serves as a trusted advisor, systems-level problem solver, and liaison to staff, families, Board of Directors, funders, and community partners. This position drives organizational alignment, supports performance improvement efforts, and enhances the CEO’s capacity to focus on strategy, growth, and stakeholder engagement. In addition, the Chief of Staff provides enterprise-wide executive oversight of Operations, Compliance, Facilities, Information Technology, and Human Resources, ensuring operational continuity, regulatory compliance, and organizational effectiveness. Acting with delegated authority from the CEO, this role functions as the organization’s central operational integrator, aligning people, systems, and infrastructure to support mission delivery and long-term sustainability.
Requirements
- Bachelor’s degree in Business, Public Administration, Nonprofit Management, Human Resources, Education, or related field
- 5+ years progressive leadership experience, including enterprise-level operational oversight
- Demonstrated experience managing people, systems, and infrastructure in a regulated environment
- Strong understanding of compliance, risk management, and organizational governance
- Excellent project management, communication, and analytical skills
Nice To Haves
- Master’s degree in education, MBA, MPA, or Organizational Leadership
- Experience in autism services, education, healthcare, or similarly regulated sectors
- Experience supporting CEOs and Boards of Directors
- Key Competencies
- Enterprise operational leadership
- Systems thinking with strong execution discipline
- Sound judgment and discretion with confidential matters
- Ability to lead through influence rather than authority
- High emotional intelligence and executive presence
Responsibilities
- Executive Operations and Organizational Leadership
- Serve as the CEO’s chief operational advisor and execution lead across all non-programmatic functions
- Translate strategic priorities into operational plans, timelines, and accountability structures
- Ensure alignment and coordination across administrative, educational, clinical, and support functions
- Act with delegated authority to resolve cross-functional issues and remove operational barriers
- Operations, Compliance and Risk Management:
- Provide executive oversight of organizational compliance with CARF, DESE, DMH, and other applicable regulatory and accreditation bodies
- Ensure organization-wide readiness for audits, site visits, licensure reviews, and accreditation surveys
- Coordinate cross-functional compliance efforts across programs, Human Resources, Facilities, and Information Technology
- Monitor regulatory changes and translate requirements into operational policies, procedures, and internal controls
- Oversee enterprise risk management, incident response coordination, and corrective action planning
- Facilities Oversight:
- Provide executive oversight of facilities operations, including maintenance, safety, accessibility, space utilization, and vendor management
- Ensure compliance with OSHA, ADA, fire code, and local safety requirements
- Lead emergency preparedness planning related to physical environments
- Oversee facilities planning for renovations, expansions, and capital improvement projects
- Information Technology Oversight:
- Provide executive oversight of organizational technology systems and infrastructure
- Ensure cybersecurity, data privacy, system reliability, and regulatory compliance
- Guide technology strategy, system improvements, and process automation initiatives
- Coordinate staff access, training, and vendor-managed IT services
- Human Resources Oversight:
- Provide executive-level oversight of all Human Resources functions, including compliance, employee relations, performance management, and workforce planning
- Ensure adherence to federal, state, and local employment laws and internal policies
- Support compensation strategy, leadership development, succession planning, and organizational design
- Serve as the executive escalation point for complex or sensitive HR matters
- Strategic Projects and Systems Management:
- Lead organization-wide initiatives related to operational improvement, accreditation readiness, and infrastructure development
- Strengthening workflows, documentation, and internal systems to improve consistency, accountability, and scalability
- Monitor organizational performance and proactively escalate risks or barriers
- Board and External Coordination:
- Support preparation of Board agendas, packets, dashboards, and follow-up actions
- Coordinate cross-functional reporting for funders, auditors, and external stakeholders
- Support partnerships, grants, and external relationships as directed by the CEO
- Culture, Performance and Accountability:
- Model Sherwood values of inclusion, safety, dignity, and person-centered service
- Promote accountability, continuous improvement, and data-informed decision-making
- Support initiatives that strengthen employee engagement, retention, and organizational health
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What This Job Offers
Job Type
Full-time
Career Level
Executive
