Oakwood School is an independent, non-sectarian, college-preparatory school for students in preschool through twelfth grade. Students come to Oakwood for an outstanding, balanced academic program led by expert, passionate teachers who foster confident self-expression and self-discovery. Our diverse community, thriving on an expansive campus, provides a home for an extended family of learners. Here, we share our unwavering commitment to a more intentional education.

Oakwood School fosters a learning environment where meaningful peer relationships and strong teacher interactions create a foundation for student growth. We believe that students thrive when they feel supported and encouraged to take risks, embracing a growth mindset as a key pillar of learning. Our educators cultivate a safe and engaging classroom atmosphere that nurtures curiosity, confidence, and a lifelong love of learning.

Located in beautiful suburban Morgan Hill, CA, Oakwood offers its faculty convenient access to many amenities, such as shops, restaurants, and a variety of outdoor recreational activities. The world-class resources of Silicon Valley, Stanford University, the University of California-Berkeley, San Francisco, and the entire Bay Area are only a short drive away. 

Summary

Oakwood School seeks a dynamic, strategic, and mission-driven Director of Enrollment Management to lead a unified enrollment strategy that includes recruitment, outreach, evaluation, and admissions efforts for new students entering Preschool through 12th Grade, as well as re-enrollment and retention of current students. The Director serves as a key member of the school’s leadership team and is responsible for advancing Oakwood’s visibility, value proposition, and student enrollment across all divisions. The Director leads a team that includes the Assistant Director of Admissions and Advancement Coordinator, while also working in close collaboration with numerous other campus departments. The ideal candidate will be both a strategist and a storyteller, combining data-driven decision-making with a deep understanding of student recruitment and family decision-making.

Essential Duties and Responsibilities (include but are not limited to)

• Develop and implement an enrollment strategy that effectively models the school’s mission, values, and culture to attract, engage, enroll, and retain mission-fit families and students.
• Create, design, and execute compelling events to promote the school and attract prospective families, including open houses, tours, parent events, information sessions, shadow visits, and community engagement activities.
• Efficiently and accurately manage the admissions and review process for three distinct divisions: Lower School, Middle School, and High School (includes International). Coordinate and guide the reading of applicant files and committee decision process.
• Maintain strong, collaborative working relationships with Division Heads to continually align on admissions processes, student assessment, application review, events, and how to represent division programs for prospective families.
• Lead a cross-functional enrollment team focused on new student recruitment, community outreach, evaluation, and admissions, working closely with the marketing and communications department.
• Work effectively and extensively with the marketing and communications department to manage a comprehensive marketing calendar aligned with the school’s enrollment cycle, create compelling enrollment marketing materials (print, online, video, and social media), and oversee enrollment-specific website content.
• Oversee the full admissions process from inquiry to enrollment, ensuring a warm, responsive, mission-centered experience for families.
• Establish, maintain, and grow strong relationships with local feeder schools and programs, community organizations, real estate professionals, and educational consultants to attract more students and families.
• Collaborate with internal departments (e.g., Advancement, Performing Arts, Athletics) to ensure alignment of events with visibility and outreach goals.
• Coordinate all aspects of the Scholarship Review process, including committee training, scheduling/conducting interviews, award notifications, and renewals.
• Collaborate with the International Student Support Coordinator on the recruitment, selection, and summer on-boarding of new international students.
• Recruit, train, and recognize a robust team of student and parent volunteers to support recruitment and retention efforts, including tour guides, Admissions Ambassadors, Welcome Committee, student speakers, and Open House volunteers.
• Develop data-informed strategies to improve yield, retention, and family fit.
• Manage the admissions software platform to optimize prospect management, event registrations, and applicant communication and review. Deliver seamless conversion to Veracross for school and families at time of enrollment.
• Provide accurate information on tuition and affordability, supporting families with timely reminders and guidance during the financial aid application process.
• Analyze and report regularly on funnel metrics, retention patterns, demographic trends, and marketing ROI.
• Forecast and track enrollment goals in collaboration with Business Office and School Heads.
• Utilize admissions and enrollment statistics and data to track progress to goals, identify trends, and inform planning and decision-making. Understand and proactively respond to local and national trends that affect independent school enrollment.

Other Duties and Responsibilities (include but are not limited to)

• Attend and lead admissions events, including Open Houses, School Visits, Information Sessions, HAWKS Days, and New Family Welcome Events.
• Attend various staff meetings, Back-to-School Nights, and other events as scheduled.
• Embody Oakwood School’s mission and values.
• Support and follow school policies and procedures.

Qualifications

• Demonstrated alignment to Oakwood’s mission, values, and philosophy.
• A bachelor's degree and at least five years of admission/enrollment management experience, or an equivalent combination of education and experience sufficient to perform the essential functions of the job. Master’s or other advanced degree preferred.
• Previous success in growing student enrollment, preferably in an independent school setting.
• Excellent interpersonal and communication skills, both written and verbal.
• Demonstrated analytical, strategic, and problem-solving ability with a keen attention to detail.
• Ability to work independently and as part of a team.
• Proven leadership, collaboration, and project-management skills.
• Experience managing a team and developing cross-functional strategies.
• Personal qualities of integrity, kindness, approachability, and a strong work ethic.

Physical Requirements & Environmental Conditions

• Ability to stand, walk, stoop, kneel, crouch, and manipulate (lift, carry, move) light to medium weights of 10-30 pounds.
• Ability to perform repetitive wrist/hand/finger movement to work on computer and/or related office equipment.
• Ability to work at a desk/computer for extended periods of time.
• Frequently required to sit, reach with hands and arms, talk and hear.
• Ordinary ambulatory skills sufficient to visit other locations on campus.
• Normal office environment and moderate noise levels.
• Occasional to frequent interruptions.

Compensation

This position has an expected salary range of $115,000 - $145,000.

Benefits

Benefits include medical, dental, and vision insurance, 403b retirement plan with employer match, paid sick leave, professional development opportunities, and on-site cardio and weight room. 

Dependent children of employees receive tuition remission (one child no-cost tuition/full-time employee), financial aid and scholarship opportunities, and on-site before and after school care.  Please visit Oakwood’s Employment webpage to learn more and access a full listing of benefits.

About Oakwood School

Oakwood School is an independent, non-sectarian, college-preparatory school for students in preschool through twelfth grade. Students come to Oakwood for an outstanding, balanced academic program led by expert, passionate teachers who foster confident self-expression and self-discovery. Our diverse community, thriving on an expansive campus, provides a home for an extended family of learners. Here, we share our unwavering commitment to a more intentional education. Located in beautiful suburban Morgan Hill, CA, Oakwood offers its faculty and staff convenient access to many amenities, such as shops, restaurants, and a variety of outdoor recreational activities. The world-class resources of Silicon Valley, Stanford University, the University of California-Berkeley, San Francisco, and the entire Bay Area are only a short drive away.

Connections working at Oakwood School