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Windward School

Windward School, a grade 7-12 college-preparatory, independent day school in vibrant West Los Angeles, seeks an experienced educator to join our World Language Department. Windward faculty and administrative leaders continually seek best practices and educational partnerships to help our students and faculty pursue their passions, engage in cutting-edge work and lead meaningful lives.

Windward’s mission, as a college-preparatory school, is to challenge each student to achieve academic excellence in a nurturing environment. Windward teachers, parents and administrators work as a team to encourage each student to be responsible, caring, well, informed, ethical and prepared, thus promoting the fullest development of the individual.

The Director of Recruitment & Benefits supports Windward School by providing leadership and oversight with respect to benefits administration, recruiting, benchmarking, performance management, employee relations, and communications. The position partners with the Associate Director of Payroll and Benefits Services and works collaboratively with school administrators, department heads, faculty, and staff to develop and implement objectives that will provide an employee-oriented culture.


Reports to: Chief Operating Officer


Primary Responsibilities:


Recruitment & Onboarding:

• Coordinates the faculty hiring process with the Division Directors and Department Chairs.

• Oversees the staff hiring process in conjunction with the appropriate department heads and COO.

• Manages the hiring checklist process for all hires, updating the HOS on a weekly basis.

• Updates/revises recruiting process steps as needed prior to the beginning of the hiring season; ensures that the steps are clearly communicated and followed.

•  Manages the job posting process, including ensuring descriptions are updated as needed.  Utilizes various independent school recruitment sites (CAIS, NAIS, etc.) as well as other sites/resources with a focus on attracting a diverse candidate pool.

• Acts as the primary point of contact for recruiters.

• Ensures interviewers have access to candidate information (resumes, SkillSurveys, etc.) during the hiring process.

•  Manages online reference verification and other candidate reference follow-up.

• Provides salary recommendation for Head of School based on Faculty Salary scale and staff benchmarking; prepares Offer Sheet for Head of School’s interview.

•  Manages onboarding and offboarding processes for employees, including seasonal coaches, guest artists, and summer camp employees.

•  Ensures all pre-hire requirements (TB Assessment, DOJ LiveScan fingerprinting, Covid vaccination) are completed prior to date of hire.

•  Oversees KissFlow onboarding, offboarding, and Activation/Deactivation workflow process.

•   Prepares and issues annual Contracts for Faculty and Staff, guest artists and seasonal coaches’ Offer Letters.

•   Maintains the HRIS (Paylocity); ensures data integrity.

•  Oversees the Norton Anti-Drug Testing Program for school bus drivers.

•  Orders new business cards.


Benefits Administration:

•   Manages benefits programs and communicates information/disseminates materials to employees, including benefit renewals and Open Enrollment materials.

•   Answers employee benefits questions; assists with resolving benefit-related concerns and issues regarding claims or coverage.

•   Administers 403b plan, including managing recordkeeper (TIAA) and investment advisor (Morgan Stanley) and ensuring fiduciary compliance in conjunction with Investment Committee.

•   Manages leaves of absence, including responding to EDD and Windward-provided disability claims; works closely with Payroll.

•  Creates and leads Wellness program initiatives.

•   Reconciles, audits, and approves benefit invoices ensuring accurate enrollment, runs reports, and coordinates with the Business Office.

•   Oversees 5500 reporting.

•   Manages Open Enrollment process and renewals of employee benefits.

•   Collects and maintains benefit-related historical documents.

•   Responds to unemployment claims.

•   Oversees Workers Compensation program, including Covid reporting.

•   Prepares Milestone Award Promissory Notes.

•   Coordinates annual Flu Shot clinic.

•   Participates in external surveys in all areas of Human Resources, including Cal-ISBOA, NAIS, and any other school related data collection services.  Using compiled data from these surveys, provides benchmarking ranges on positions at the school.



•   Ensures regulatory compliance with Federal, State, and Local laws.

•   Consults with legal counsel and insurance brokers as appropriate.

•   Annually reviews and makes recommendations to the Head of School and COO for improvement of the School’s policies, procedures and practices on personnel matters.

•   Updates and disseminates the Employee Handbook and related employee documents (Mandated Reporting, PPC Assumption of Risk, etc.) annually to coincide with contract renewal in early Spring; ensures all employees review and acknowledge these documents, as well as the Crisis & Safety Manual.

•  Communicates changes in school personnel policies and procedures.

• Prepares and files required annual reporting (EEO, CA Pay Data Report, ACA, CMS Annual Disclosure, etc.).

•  Ensures Harassment Prevention and other mandatory training are completed per required timeframes.


Employee Relations:

•   Consults with legal counsel as appropriate or as directed on employee relation matters.

•   Assists in managing employee relations issues.

•   Provides consultancy advice to Division Directors and Department Chairs on personnel matters.

•   At the direction of the Head of School or the COO, takes the lead or provides support, including recommendations, on employee relations investigations involving employees.



•   Bachelor’s degree with 5+ years of hands-on, direct experience in the field of Human Resources management required; HR Certification (PHR, SPHR, or SHRM-CP/SCP) and non-profit experience preferred.

•   Experience with Paylocity payroll and HRIS systems.

•   Excellent organization, time management, and analytic skills.

•   Ability to be self-directed, handle multiple tasks and priorities, solve problems and demonstrate leadership skills within a team environment.

•   Outstanding oral and written communication and interpersonal skills.

•   Ability to use discretion with confidential information.

•   Proficiency in Microsoft Office and Google Office; willingness to learn new systems and techniques.
•   Proven ability to work as a positive, enthusiastic member of a team.


Salary Range: $110,000 – $140,000, depending on experience.

This is a great chance to be part of a dynamic, close-knit, independent school culture and community.

We offer competitive compensation and benefits, including:

•   Medical, dental, vision insurance

•   Paid Holidays, Vacation and Wellness days

•   Retirement Plan, including up to 6% employer match

•   School-paid Life and Disability Insurance

•   Flexible Spending Account Plans

•   Annual $2,000 FlexCheck

•   Annual $2,000 Lunch Allowance

•   Access to Peak Performance Center to promote physical and mental health

•   Wellness Initiatives

•   Employee Assistance Program

•   Tuition Remission

•   Nurturing, supportive and inclusive community

•   And much more!

For more information about Windward School, see our website:

To Apply: All interested candidates should submit a resume and a letter of interest via the Apply link.


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