Human Resources Generalist

Staff / Full-Time

Dexter Southfield School, Brookline, MA

About Dexter Southfield 

Dexter Southfield is an independent day school where boys and girls in Pre-K through Class 12 develop their individual talents and build an ethical foundation for life. Students learn to lead and serve with character, confidence, and compassion. Our 36-acre campus is located just minutes from Boston’s best museums, libraries, hospitals, performing arts venues, colleges, and universities—all of which serve as an extension of our classrooms. At Dexter Southfield, we approach everything we do with enthusiasm and commitment, living by our School’s motto: “Our Best Today, Better Tomorrow.”

About Our Team

Our Human Resources team oversees all disciplines of human resources management including recruitment and retention, compensation and benefits, employee relations, employment law and compliance, performance management, leave management, strategic development, training, compliance, and risk management. Given our rapid growth in recent years, we are looking to add a full-time HR generalist to our team. This position will report to the Director of Human Resources.

About You

You are passionate about a career in human resources and demonstrate confidence, professional discretion, and an eye for detail in everything you do. You are a self-starter who enjoys making a positive impact in the lives of others. Your organizational and relationship skills allow you to offer great support and customer service to employees while your curiosity and research skills ensure you remain current in the ever-changing world of labor law, systems, and best practices. Above all, you enjoy working with people and want to see them succeed.

To be successful in this role, you must be able to:

  • Manage employment-related inquiries from applicants, employees, and supervisors with respect, knowledge, and confidence; refer complex and/or sensitive matters to appropriate team members
  • Support recruitment, hiring, and retention initiatives (job postings, career fairs, interviews, etc.)
  • Oversee the full-cycle onboarding process (introduction and orientation to immersion and engagement)
  • Ensure ongoing performance management reviews for all employees (90-day, interim, and annual)
  • Assist with the annual Open Enrollment process, from insurer negotiations to employee enrollment
  • Manage HR information management systems, including running and analyzing reports
  • Maintain and prepare records and reports with an eye toward strategic oversight and compliance
  • Coordinate leaves of absence (FMLA, PFML, long- and short-term disability, personal leaves, etc.)
  • Review, track, and ensure compliance with mandatory and non-mandatory trainings, continuing education, certifications, licensures, and other work assessments.
  • Conduct quarterly compliance reviews and annual policy reviews
  • Research, analyze, and prepare data for presentations to senior leadership
  • Maintain knowledge of and compliance with federal, state, and local employment laws and regulations, labor trends, best practices, and new technologies
  • Establish effective working relationships with faculty, staff, brokers, and vendors
  • Provide backup support for payroll processing
  • Perform other duties, as assigned


  • Bachelor’s degree with at least three years of HRM experience; SHRM certification highly desirable
  • Proficiency using Microsoft Office Suite (Word, Excel, PowerPoint, Outlook, etc.)
  • Familiarity with Paycor HRIS and Blackbaud systems highly desired
  • Verifiable history exercising discretion when dealing with highly sensitive and confidential matters
  • Exemplary organizational skills; ability to meet deadlines with maximum precision and minimal supervision
  • Knowledge of labor laws and benefit programs (ACA, ADA, FMLA, FLSA, FSA, HRA, MPFML, etc.)
  • Understanding of employee relations and conflict resolution strategies
  • Ability to communicate effectively (orally, written, non-verbal) and build trust among diverse constituencies
  • Commitment to actively promote and contribute to an engaging and inclusive workplace for all
  • Ability to be flexible, effectively manage stress, and adapt to changing work priorities

At Dexter Southfield, we promote a culture of excellence that extends beyond academics, athletics, and the arts. We value a diverse and inclusive community in which different identities and perspectives are accepted and respected to create a sense of belonging for all.

Interested candidates are encouraged to apply online through Dexter Southfield’s Career page.

Dexter Southfield School

Brookline, MA
Early Childhood, Elementary, Middle School, High School
All Gender, Boys, Girls