Dean of Student Life

Our Purpose

Our Purpose is to inspire and challenge students to better themselves and the world around them.

Our Core Behaviors

Want to know whether you would be a good cultural fi t on our team at Pilgrim? We strongly value teamwork as the fabric of our professional community. We are looking for team players who are:

Humble - They are more concerned with the success of the team than with getting credit for their contributions. Humble people are quick to point out the contributions of others and slow to seek attention for their own. They emphasize team over self and defi ne success collectively rather than individually. Humble team players are not afraid to honestly acknowledge the skills and talents they bring to the team, though never in a proud or boastful way.

Driven - They have the desire to work hard and do whatever is necessary to help the team succeed. Their pursuit of self-improvement and desire to contribute is evident. They understand that their personal growth supports the success of their students and peers. Driven people almost never have to be pushed to work harder because they are self-motivated and diligent.

Relational - They use common sense about people and understand the importance of forming and maintaining positive relationships. Relational people value what is happening in a group situation and how to connect with others in the most eff ective and meaningful way. They use good judgment about how their words and actions impact group dynamics. They have a desire for strong connections with people in order to contribute to eff ective teamwork and a collaborative environment.

Our Anchors

Want to know what sets Pilgrim apart in our approach to education? You would be a great fi t if your beliefs and practices align with our three anchors below:

Joyful Experience - We foster a strong sense of community and honor traditions that bring us together. Our commitment to a healthy school environment ensures that every student feels safe and supported, while off ering student choice empowers them to take an active role in their education.

Focus on Mastery - We hold students to high academic standards and provide students with a clear understanding of what they are expected to learn, where they are in the learning process, and through feedback, how to improve. Students engage in authentic and challenging learning experiences that prioritize depth and retention over surface understanding and build future-ready skills.

Personal Attention - We celebrate every identity, creating an inclusive environment where all community members feel valued. Strong connections between faculty, students, and parents are fostered to ensure that each student is seen and known. By focusing on individual student needs, we support the unique development and success of every child in our care.

Pilgrim at a Glance

Pilgrim School, founded in 1958, is a mastery-based, college preparatory school in Koreatown with an inclusive community serving Preschool through 12th Grade.

7:1 Overall Student:Teacher Ratio

375 Students from Preschool to 12th Grade

Average Class Size is 12-15 students

57% Faculty and Staff identify as people of color

Position Summary

Join Pilgrim as the Dean of Student Life, where you’ll lead dynamic student life programming that inspires joy, connection, and authentic student growth. In this dynamic role, you’ll design and lead student life programming that brings our school’s mission to life — from student leadership and club development to spirited events and service-learning opportunities. You’ll also play a key role in leading the pilot phase of our innovative Impact Program, guiding students as they explore social and environmental issues and develop their own signature projects. Throughout, you’ll cultivate a sense of belonging and joy, weaving together experiences that help every student feel seen, known, and valued. If you’re passionate about fostering community, elevating student experiences, and creating a culture of joyful engagement, we invite you to join us at Pilgrim.

Major Areas of Responsibility

●Serve as the faculty advisor for student leadership in the Middle School and High School.

●Produce, plan, and execute student life events in the Middle and High School.

●Approve and oversee student clubs and organizations, and develop structures for long-term success and involvement in these groups.

●Support the development of a robust program of community service and engagement for students, including the management of the Mobile Serve app.

●With the Secondary Leadership Team, help design and facilitate student orientation, back to school and end of school activities.

●Plan and lead division assemblies and daily morning announcements.

●Keep the Pilgrim community informed about student life events, including contributing to the weekly newsletter and supporting students' engagement with Pilgrim social media.

●Lead the Impact Program pilot in the High School, including teaching the course. The Impact Program is a three-year, experiential learning initiative where students explore social and environmental issues, develop leadership skills, and design a signature project to create positive change.

●Teach one additional course in the Secondary School.

Required Qualifications

●Master’s degree or higher in a relevant fi eld is strongly preferred. Bachelor’s degree is required.

●Minimum of 5 years of teaching experience in a K-12 setting, preferably at an independent school.

●Demonstrated leadership experience within a school environment, such as managing student programs or initiatives.

●Excellent organizational, communication, and relationship-building skills.

●Strong ability to work collaboratively with students, faculty, and families to support school culture and student well-being.

If you do not meet all qualifications but feel you are a good fi t for this position, we welcome your submission.

Preferred Background

●Experience with or understanding of experiential, project-based learning programs (like the Impact Program) and student-led service initiatives.

●Proven ability to mentor and inspire students to develop leadership skills and civic engagement.

●Experience supporting or coordinating student leadership, service learning, or other co-curricular programs.

●A passion for student life programming that integrates academic, social, and community-focused goals.

Salary Range and Benefits The salary range for this position is $78,000-$110,000 depending on experience and qualifications. We offer a full and robust range of medical, dental and vision benefits, participation in a 403b retirement plan, which we will match up to 4%, and life insurance. More information about all of our benefits will be provided during the interview process.

Timeline and Start Date The deadline to apply for this position is ongoing until the position is filled. The start date for this position is August 1, 2025. Please note that employment is subject to Live Scan clearance and reference checks prior to beginning employment.

How to Apply To be fully considered for the position, please send your resume, cover letter, and references (including a supervisor) to Ryan Grady, Director of Secondary School at employment@pilgrim-school.org.

Pilgrim School provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, national origin, age, disability or genetics. In addition to federal law requirements, Pilgrim School complies with applicable state and local laws governing nondiscrimination in employment.