Director of Human Resources

Director of Human Resources
Job Description

The Director of Human Resources will design, administer, implement, oversee, support, and evaluate the human resource functions of The Windward School. Supervising and managing a variety of human resource and labor relation functions, the Director of Human Resources will report directly to the Head of School and will ensure the effective and efficient administration of all aspects of personnel-related services, policies, negotiated agreements, and programs.  The Director of Human Resources will support administrators in hiring, on-boarding, employee orientation, training, performance management, employee relations, and employment law interpretation.


  • Bachelor’s Degree in Human Resources or related field required.  Master’s/MBA degree preferred.
  • Minimum of 5 to 10 years of Human Resources experience in a managerial role.
  • Demonstrated success at a similar organizational level.
  • Strong supervisory, organizational, technical, and analytical skills.
  • Independent school experience preferred.
  • Ability to communicate effectively with people at all levels of the organization.
  • Ability to effectively deal with multiple priorities, functions, and activities.
  • Working knowledge and skills of basic business software, including MS Office Suite (Word, Excel, PowerPoint).  Blackbaud database experience desirable.


Duties and Responsibilities



  • Maintain secure and confidential human resources-related files and records in accordance with data retention policies.
  • In collaboration with Senior Administrators, prepare and maintain accurate job descriptions.
  • Coordinate annual review of union and non-union employee handbooks and make any necessary recommendations for change.


  • Ensure compliance with all federal, state, and local employment practice regulations.
  • Keep abreast of current and potential changes in regulations in relation to employment practices.
  • Analyze the impact of any changes on the School and proactively recommend policy to maintain compliance.
  • Establish and oversee protocol for background checks for all employees, including fingerprinting.
  • Oversee faculty and staff attendance using Paycom software.
  • Be knowledgeable of all provisions of teachers’ union contract and ensure that the contract is correctly implemented

Benefit Plans

  • Administer all employee benefit plans and ensure effective and timely communication regarding these plans to all employees.
  • Manage annual enrollment and mid-year changes for health, life, disability, and dental benefits.
  • Educate employees on benefit options and coordinate meetings with outside professionals.
  • Review monthly benefit invoices for accuracy.
  • Work with Business Office payroll to make sure correct employee deductions are being withheld.

Employee Retention

  • Coordinate with newly-hired employees to complete all necessary paperwork and background checks required for their position.
  • Complete periodic job description audits and classify employees’ exempt or non-exempt status as appropriate under the Fair Labor Standards Act.
  • Update employee files.
  • Establish procedures to resolve personnel issues including proper documentation.
  • Manage recruiting lifecycle including posting job openings, coordinating candidate visits, and managing recruitment for non-academic positions.
  • Conduct exit interviews with all outgoing employees, compiling results annually for administrative review.

Compensation and Budgeting

  • Research statistics to help establish salaries for non-union/union employees.

Professional Development/Training

  • Ensure non-academic employees have access to training and professional development by establishing a cohesive training model for all staff.
  • Provide training to all employees such as annual training on sexual and other forms of harassment, sexual abuse reporting, and other applicable topics.

All other duties as requested by the Head of School.

This position is exempt.

This position supervises the current HR Representative, the HR office is located in White Plains, NY. 

Send all resumes to

The position reports to the Head of School (Associate Head of School/CFO).