Chesapeake Bay Outward Bound School
Director of People & Operations
Chesapeake Bay Outward Bound School, Baltimore, Maryland, United States, 21276
2 days ago Be among the first 25 applicants
Description The Director of People & Operations is responsible for overseeing the organization’s Human Resources, administrative operations, including facilities management, and organizational systems. This role ensures the organization has the people, systems, and processes needed to operate effectively, scale sustainably, and support a healthy, inclusive, and high-performing workplace. The Director manages a team of six and partners closely with the Executive Director and Leadership Team to strengthen leadership capability, build successor readiness, and enable executive capacity for strategic priorities.
Essential Duties And Responsibilities Human Resources
Lead organizational people strategy aligned with mission, values, and long‑term growth plans
Develop and implement HR initiatives and policies that promote a healthy, diverse, and inclusive work environment
Oversee HR operations including employee relations, performance management, payroll coordination, benefits administration, and workers’ compensation
Lead, review and update HR policies and procedures, including hiring, compensation, benefits, and performance management in accordance with applicable federal/state laws
Develop leadership and manager capability across the organization, strengthening accountability and succession readiness
Partner with leaders to support hiring, onboarding, development, and retention
Serve as a trusted advisor to managers on employee relations, performance, and organizational effectiveness
Administrative Leadership
Oversee and support staff responsible for HR administration and office operations, including recruitment coordination, employee record management, benefits support, payroll coordination, and day‑to‑day office operations
Manage and improve administrative processes to ensure organizational efficiency and compliance
Serve as the primary point of contact for contracts, vendor relationships, and administrative policies
Oversee organizational compliance, risk management, and employment‑related legal requirements
Maintain and build trusted relationships with internal teams and external partners
Facilities and Operations
Oversee facilities team for all office locations, including security and maintenance
Lead cross‑functional teams along with organizational leadership to establish long‑term business goals and operational plans
Oversee technology strategy and resources to ensure smooth operations
Support infrastructure planning for organizational growth and multi‑site operations
Implement policies and practices that foster transparency, accountability, and a positive work environment
Leadership & Organizational Development
Strengthen leadership effectiveness and support learning team members through coaching, systems‑building, and clarity of roles
Identify leadership gaps and develop emerging leaders and successors through a robust training and development strategy
Build organizational capacity that enables the Executive Director and leadership team members to focus on strategy, partnerships, and external leadership
Requirements Minimum Qualifications
Bachelor’s degree in Human Resources, Business Administration or related field; advanced degree preferred
5+ years of experience in administration, HR, or organizational development
Strong knowledge of HR practices, compliance, operations and organizational policies
Excellent organizational, communication, and leadership skills
Proficiency with office technology and HR systems
Benefits
Employer contribution of 70% for medical, dental & vision insurance for the employee and their children, if applicable
15 days of paid time off (PTO) which accrue per pay period
Up to 8 weeks of paid family/medical leave
13 paid holidays
401(k) retirement plan with a match (match 3% of employee’s salary after 6 months employment)
Long‑term disability, short‑term disability, and a $25,000 life insurance policy at no cost to the employee
Pre‑tax savings cafeteria plan: healthcare FSA, dependent care FSA, HSA
Pre‑tax commuter/transit benefits
Employee assistance program (EAP)
Mutual of Omaha supplemental insurance
Pro Deals: discounts from outdoor industry vendors for outdoor professionals
Physical Demands and Work Environment
Ability to sit at a desk or computer 90% of the time or greater
Note This job description in no way states or implies that these are the only duties to be performed by the employee(s) of this position. Employees will be required to follow any other job-related instructions and to perform any other job-related duties requested by any person authorized to give instructions or assignments. All duties and responsibilities are essential functions and requirements and are subject to possible modification to reasonably accommodate individuals with disabilities. To perform this job successfully, the employee(s) will possess the skills, aptitudes, and abilities to perform each duty proficiently. Some requirements may exclude individuals who pose a direct threat or significant risk to the health or safety of themselves or others. The requirements listed in this document are the minimum levels of knowledge, skills, or abilities. This document does not create an employment contract, implied or otherwise, other than an at‑will relationship.
Seniority Level
Director
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Description The Director of People & Operations is responsible for overseeing the organization’s Human Resources, administrative operations, including facilities management, and organizational systems. This role ensures the organization has the people, systems, and processes needed to operate effectively, scale sustainably, and support a healthy, inclusive, and high-performing workplace. The Director manages a team of six and partners closely with the Executive Director and Leadership Team to strengthen leadership capability, build successor readiness, and enable executive capacity for strategic priorities.
Essential Duties And Responsibilities Human Resources
Lead organizational people strategy aligned with mission, values, and long‑term growth plans
Develop and implement HR initiatives and policies that promote a healthy, diverse, and inclusive work environment
Oversee HR operations including employee relations, performance management, payroll coordination, benefits administration, and workers’ compensation
Lead, review and update HR policies and procedures, including hiring, compensation, benefits, and performance management in accordance with applicable federal/state laws
Develop leadership and manager capability across the organization, strengthening accountability and succession readiness
Partner with leaders to support hiring, onboarding, development, and retention
Serve as a trusted advisor to managers on employee relations, performance, and organizational effectiveness
Administrative Leadership
Oversee and support staff responsible for HR administration and office operations, including recruitment coordination, employee record management, benefits support, payroll coordination, and day‑to‑day office operations
Manage and improve administrative processes to ensure organizational efficiency and compliance
Serve as the primary point of contact for contracts, vendor relationships, and administrative policies
Oversee organizational compliance, risk management, and employment‑related legal requirements
Maintain and build trusted relationships with internal teams and external partners
Facilities and Operations
Oversee facilities team for all office locations, including security and maintenance
Lead cross‑functional teams along with organizational leadership to establish long‑term business goals and operational plans
Oversee technology strategy and resources to ensure smooth operations
Support infrastructure planning for organizational growth and multi‑site operations
Implement policies and practices that foster transparency, accountability, and a positive work environment
Leadership & Organizational Development
Strengthen leadership effectiveness and support learning team members through coaching, systems‑building, and clarity of roles
Identify leadership gaps and develop emerging leaders and successors through a robust training and development strategy
Build organizational capacity that enables the Executive Director and leadership team members to focus on strategy, partnerships, and external leadership
Requirements Minimum Qualifications
Bachelor’s degree in Human Resources, Business Administration or related field; advanced degree preferred
5+ years of experience in administration, HR, or organizational development
Strong knowledge of HR practices, compliance, operations and organizational policies
Excellent organizational, communication, and leadership skills
Proficiency with office technology and HR systems
Benefits
Employer contribution of 70% for medical, dental & vision insurance for the employee and their children, if applicable
15 days of paid time off (PTO) which accrue per pay period
Up to 8 weeks of paid family/medical leave
13 paid holidays
401(k) retirement plan with a match (match 3% of employee’s salary after 6 months employment)
Long‑term disability, short‑term disability, and a $25,000 life insurance policy at no cost to the employee
Pre‑tax savings cafeteria plan: healthcare FSA, dependent care FSA, HSA
Pre‑tax commuter/transit benefits
Employee assistance program (EAP)
Mutual of Omaha supplemental insurance
Pro Deals: discounts from outdoor industry vendors for outdoor professionals
Physical Demands and Work Environment
Ability to sit at a desk or computer 90% of the time or greater
Note This job description in no way states or implies that these are the only duties to be performed by the employee(s) of this position. Employees will be required to follow any other job-related instructions and to perform any other job-related duties requested by any person authorized to give instructions or assignments. All duties and responsibilities are essential functions and requirements and are subject to possible modification to reasonably accommodate individuals with disabilities. To perform this job successfully, the employee(s) will possess the skills, aptitudes, and abilities to perform each duty proficiently. Some requirements may exclude individuals who pose a direct threat or significant risk to the health or safety of themselves or others. The requirements listed in this document are the minimum levels of knowledge, skills, or abilities. This document does not create an employment contract, implied or otherwise, other than an at‑will relationship.
Seniority Level
Director
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