Chess Instructor | Fall

Chess Wizards•Chicago, IL

14d•$45 - $65•Onsite

About The Position

Chess Wizards is seeking enthusiastic, reliable instructors for its after-school chess enrichment program serving elementary students in the greater Chicago metropolitan area. Instructors lead interactive classes for groups of 10–15 students, use a structured curriculum to teach chess fundamentals and sportsmanship, and create a positive, engaging classroom environment. The role includes supervising students in accordance with school safety protocols, traveling to local school sites, and arriving prepared and on time. Classes are held on weekday afternoons, with start times typically between 2:00 PM and 5:00 PM. Instructors teach between one and five classes per week, depending on local school availability. A typical class session lasts approximately 90 minutes, including setup, instruction, and post-class responsibilities. Pay is $45–$65 per class. Mileage reimbursement is provided for trips exceeding 15 miles one way from the instructor’s home or work location. Work locations are assigned based on available schools and classes. Chess Wizards provides full training, ongoing support, curriculum and materials, free chess classes, opportunities for advancement, work flexibility, and a positive company culture. The position is based in Chicago, IL. Relocation assistance is not provided; candidates must reside in the area or relocate at their own expense. Applicants must submit a resume and complete a required questionnaire.

Requirements

Experience working with groups of children, such as through teaching, tutoring, coaching, camp counseling, or similar work.
Ability to lead a class independently and create interactive, friendly, and fun sessions.
Professional, positive, and kid-friendly demeanor.
Genuine desire to be a positive role model and promote good sportsmanship.
Strong grasp of chess fundamentals, including piece movement, basic strategy, and simple tactics, and ability to explain them in an age-appropriate way.
Ability to connect chess problem-solving to real-life problem-solving.
Reliable personal transportation and ability to drive between locations.
Availability on weekday afternoons for class start times between 2:00 PM and 5:00 PM, for one to five classes per week depending on local school availability.
Commitment to school safety protocols, student well-being, and strict adherence to safety and school policies.
Strong punctuality and time-management skills.
Submit a resume detailing relevant experience and complete the required application questionnaire.
Must currently reside in the Chicago area or be willing to relocate at own expense.

Responsibilities

Lead fun, interactive chess classes for groups of 10–15 elementary students.
Use the structured curriculum to teach chess fundamentals and promote good sportsmanship.
Guide activities, engage students, and redirect behavior when needed.
Manage a lively classroom with confidence and positivity.
Encourage problem-solving, creativity, and critical thinking.
Follow school safety protocols and supervise students 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.