[Summer 2026] Elementary Chess Instructor

DREAM • New York, NY

17h • Onsite

About The Position

Originally founded in 1991 as Harlem RBI, DREAM has grown to annually serve more than 2,500 youth across East Harlem and the South Bronx through a network of seven PreK-12, extended-day, extended-year DREAM Charter Schools and community sports-based youth development programs. Through our commitment to rigorous academics, social-emotional learning, deep family and community engagement, and health and wellness, we create lifelong learners who are equipped to fulfill their vision of success in and out of the classroom. We dream big, as well, with an aggressive five-year plan to expand to serve 3,500 students across seven schools—growing our organization’s impact and leveling the playing field for all children. To learn more, visit wearedream.org. Reporting to the Dean of Student Life, Middle School After School Chess Instructors facilitate engaging and developmentally appropriate chess instruction for students in REAL Kids and DreamBuilders—DREAM’s nationally recognized after school program. Using a provided curriculum, instructors teach foundational and advanced chess strategies while fostering critical thinking, problem-solving, focus, and sportsmanship. In addition to direct instruction and structured gameplay, instructors guide students in using a designated computer-based chess program each week to reinforce skills, practice tactics, and track progress. Instructors lead 45-minute sessions for groups of 18–20 middle school students, supported by one Youth Worker.

Requirements

• Must be at least 18 years of age by the role’s start date
• High school diploma required
• Ability to deliver a structured chess curriculum with confidence, adapting pacing and support to ensure student engagement and skill development
• Clear passion for specialty area
• Understanding of effective youth development strategies and conflict resolution
• Exemplary social, organizational, and communication skills
• Dedication to the program and ability to collaborate with colleagues to ensure a positive, productive youth experience
• Ability to work in-person during all program hours required
• A strong belief in the mission and values of DREAM, including the belief that all students can succeed, and a deep desire to make a difference in the lives of our students, families, and community

Nice To Haves

• Bachelor’s degree or certification in related field preferred
• 2+ years experience working with groups of youth, or similar experience preferred

Responsibilities

• Facilitate and deliver structured chess lessons for middle school students using a provided curriculum aligned to the DREAM program model
• Lead engaging instruction that builds strategic thinking, problem-solving skills, focus, and sportsmanship, culminating in a final tournament, showcase, or skills-based competition
• Guide students in using a designated computer-based chess program weekly to reinforce concepts, practice tactics, and monitor progress
• Collaborate with Youth Workers, the Dean of Student Life, and the Associate Director of Extended Learning and Enrichment to provide a cohesive and engaging experience for students
• Embed literacy and academic vocabulary throughout instruction (e.g., chess notation, strategic terminology, reflective discussions)
• Prepare all materials and technology prior to sessions and ensure thorough clean-up and proper storage afterward
• Encourage positive participation, teamwork, and respectful competition among students
• Serve as a positive role model while demonstrating professionalism and strong classroom management
• Implement all health and safety protocols as required, including ensuring student safety and responding appropriately to any incidents

Benefits

• 403(b) retirement plan, with employer matching up to 4% after one year of employment (12-month continuous period) in which you work a minimum of 1,000 hours
• Disability benefits
• Referral bonuses
• Access to our Employee Discount Program, offering savings on travel, entertainment, retail, and more
• High-performing part-time staff have the opportunity to apply for the DREAM Teaching Fellowship, through which they can earn a Bachelors or Masters degree and become full-time teachers at DREAM

What This Job Offers

• Job Type: Part-time
• Career Level: Entry Level
• Education Level: High school or GED
• Number of Employees: 251-500 employees