The Winston School

Teaching and Staff Jobs at The Winston School

The Winston School is a small independent day school in Del Mar, California, enrolling roughly 100 middle and high school students who are bright and creative yet have struggled in traditional academic environments. Del Mar sits on the San Diego County coast north of La Jolla, where oceanside neighborhoods and year-round Mediterranean weather create a distinct setting for learning. The proximity to Pacific beaches, coastal trails, and San Diego's museums means outdoor education and field-based instruction integrate naturally into classroom work.

At this enrollment scale, The Winston School faculty know every student and family across the entire school. The school's mission centers on helping students unlock potential after underperformance elsewhere. This requires teachers who combine subject expertise with adaptability and curiosity about how individual learners progress. Rather than delivering fixed curriculum to a pre-sorted cohort, faculty diagnose learning needs and adjust instruction accordingly. Many students arrive carrying a history of academic frustration; teaching here means rebuilding both skills and confidence simultaneously.

Working at The Winston School means joining a collaborative environment where colleagues regularly discuss student progress and strategy. You know your students' families, their specific obstacles, and the incremental wins that matter most. There is no anonymity—only direct visibility into the difference your instruction makes. The school does not require prior experience in specialized education settings. It seeks teachers intellectually curious, adaptable, and committed to helping students reconnect with learning as something possible.

Both middle and high school departments hire regularly in core academics and electives. Compensation aligns with San Diego County independent school norms, reflecting the school's commitment to attract skilled educators in a high-cost coastal region.

*Explore current teaching and staff openings at The Winston School.*