Assistant Chess Instructor - Fall

Why Join Us?

• Competitive Pay: $25 – $35 per class (Typical class time is approximately one hour and thirty minutes, including pre-class setup, instructional time, and post-class responsibilities)
• Flexible Hours: Teach a minimum of 1 class up to a maximum of 5 classes per week; classes are scheduled on weekday afternoons with start times typically falling between 2:00 PM and 5:00 PM at various local schools
• Travel Compensation: Mileage reimbursement provided for trips over 15 miles one way (30 miles roundtrip) from your home or work location; work locations are assigned by the manager based on available schools and classes in your area
• Skill Development: Excellent opportunity to gain hands-on teaching experience

What You’ll Do

• Assist the Chess Instructor in setting up and managing a fun, interactive chess class for 15–22 elementary students
• Provide one-on-one or small-group support to students, helping them practice piece movements and understand basic concepts
• Support the Chess Instructor in guiding activities, keeping students engaged, and reinforcing positive behavior
• Follow the structured curriculum and promote good sportsmanship alongside the Chess Instructor
• Manage a lively classroom with confidence and positivity
• Encourage problem-solving, creativity, and critical thinking
• Follow school safety protocols, including supervision during arrival, dismissal, and in-class activities
• Travel to various local school sites for each session
• Arrive on time, prepared, and ready to engage students

Required Qualifications

• Genuine interest in working with groups of elementary students
• Experience (teaching, tutoring, camp counseling, or similar) is a plus
• Ability to follow direction, support the Chess Instructor’s classroom management, and help create interactive, friendly, and fun sessions
• Upbeat, engaging demeanor; professional, positive, and kid-friendly attitude
• Genuine desire to be a positive role model and promote good sportsmanship
• Strong grasp of chess fundamentals; able to clearly and confidently explain piece movement, basic strategy, and simple tactics in an age-appropriate way
• Ability to connect chess problem-solving to real-life problem-solving
• Reliable personal transportation and the ability to drive between locations
• Availability on weekday afternoons (class start times between 2:00 PM and 5:00 PM) to teach 1–5 classes per week; the specific number depends on availability at local partner schools
• Commitment to implementing school safety protocols to protect students’ well-being; strong record of reliability and strict adherence to safety and school policies
• Strong punctuality and time-management skills

As part of your application, you will be asked to complete a required questionnaire related to your interest in the role, your experience working with children, and your qualifications to teach chess, among other topics.

We Offer

• Full training and ongoing support
• Full curriculum and materials
• Free chess classes
• Opportunities for advancement to Chess Instructor
• Work flexibility and great company culture

This position is based in Boylston, MA. Relocation assistance is not provided; candidates must be currently residing in the area or willing to relocate at their own expense.