Director of Education

Overview

Position Type: Full-Time

Reports To: Executive Director

Works Closely With: Chief Program Officer, Programs Team, and Education Committee

Salary Range: $65,000 – $75,000

Start Date: Summer 2026 (target: June; flexible for the right candidate)

About OWLS 

OWLS empowers youth by opening pathways to growth and opportunity. We combine lacrosse, mentorship, and academic support to promote personal growth, school success, and postsecondary readiness for youth in underserved communities. Our work is rooted in long-term relationships with students and families, supporting young people from elementary school through high school with consistent guidance, academic support, and access to new opportunities. As OWLS continues to grow, we are investing in stronger academic systems and a direct tuition scholarship program to expand access while maintaining high-quality, consistent support across our programming sites on the west and south sides of Chicago.

Position Summary 

The Director of Education leads academic support for OWLS students in the Junior Academy (grades 4–8) and Academy Scholars (grades 9–12) programs. This role focuses on helping students succeed in school and prepare for high school and postsecondary opportunities. Responsibilities include tracking academic progress, coordinating tutoring and support, guiding high school placement and college readiness, and supporting the implementation of OWLS’ scholarship program. This is a hands-on, direct-service role—working directly with students, families, and schools—while also building systems to ensure consistent, high-quality support across all sites.

Core Responsibilities

Student Academic Support & Family Engagement

• Track student academic performance 
• Coordinate academic support plans
• Maintain regular communication with families and document interactions

Academic Monitoring & Intervention Systems

• Build and manage systems for tracking GPA, attendance, engagement, and key student outcomes across programs
• Identify and support students needing intervention
• Maintain academic records and student pathway tracking

High School Transition & Placement

• Guide students through high school exploration and applications
• Track high school placement outcomes
• Advise on school fit and coordinate with high school admissions teams

Postsecondary Readiness

• Support college exploration and applications
• Guide financial aid and FAFSA processes, ensure students meet key milestones

Tutoring, Study Halls, and Academic Programming

• Coordinate tutoring and academic supports, track participation and outcomes
• Facilitate and/or oversee structured study halls
• Deliver and support workshops (study skills, SEL, test prep)
• Integrate academic supports into program sessions

Scholarship Program Coordination

• Support application review and family engagement
• Coordinate with schools and financial aid offices
• Monitor student progress for scholarship renewal
• Assist with disbursement and reporting

School & Community Partnerships

• Build relationships with partner high schools and coordinate student visits
• Maintain awareness of selective enrollment, private, and charter school landscape

Team Collaboration & Leadership

• Collaborate with leadership and programming team
• Prepare reports for leadership and Board

Qualifications

Education & Experience

• Bachelor’s degree required
• 3–5 years experience working with middle or high school students
• Experience in academic advising preferred
• Experience working with schools and families

Skills & Attributes

• Strong organizational and tracking skills
• Excellent communication skills
• Self-motivated and adaptable
• Knowledge of sports-based youth development is a plus

How to Apply

Submit a resume and cover letter to:

Sam Angelotta, Executive Director

sama@owlslacrosse.org

Applications will be reviewed on a rolling basis until the position is filled. OWLS is an equal opportunity employer and strongly encourages candidates from diverse backgrounds and experiences to apply.