Chess Instructor | Fall

Chess Wizards • Darien, CT

14d • $50 - $75 • Onsite

About The Position

Chess Wizards is seeking enthusiastic, reliable instructors for its after-school enrichment program in Darien, Connecticut. Instructors lead fun, interactive chess classes for groups of 10–15 elementary students, using a structured curriculum to teach chess fundamentals and promote sportsmanship. The role involves independently guiding activities, keeping students engaged, redirecting behavior when needed, and maintaining a positive classroom environment while encouraging problem-solving, creativity, and critical thinking.

Classes take place at various local schools 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 commitment is approximately one hour and thirty minutes, including setup, instruction, and post-class responsibilities. Instructors travel between school sites and follow school safety protocols, including supervising students during arrival, dismissal, and class activities. Full training, curriculum, materials, and ongoing support are provided.

Requirements

• Experience working with groups of children through teaching, tutoring, coaching, camp counseling, or similar work.
• Ability to lead a class independently and create interactive, friendly, and fun sessions.
• Professional, positive, kid-friendly demeanor and an upbeat, engaging approach.
• Genuine desire to be a positive role model and promote good sportsmanship.
• Strong grasp of chess fundamentals, including the ability to 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 ability to drive between locations.
• Availability on weekday afternoons for class start times between 2:00 PM and 5:00 PM, to teach one to five classes per week depending on local school availability.
• Commitment to implementing school safety protocols and a strong record of reliability and adherence to safety and school policies, as the instructor supervises children independently.
• Strong punctuality and time-management skills.
• Currently reside in the Darien, Connecticut area or be willing to relocate at personal expense; relocation assistance is not provided.
• Submit a resume detailing relevant experience with children and teaching, tutoring, or classroom work.
• Complete the required application questionnaire about interest, experience working with children, and chess-teaching qualifications.

Responsibilities

• Lead fun, interactive chess classes for 10–15 elementary students.
• Use the structured curriculum to teach chess fundamentals and promote good sportsmanship.
• Guide activities, keep students engaged, and redirect behavior when needed.
• Manage a lively classroom with confidence and positivity.
• Encourage problem-solving, creativity, and critical thinking, including connecting chess problem-solving to real-life problem-solving.
• 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.

Benefits

• Competitive pay of $50–$75 per class.
• Mileage reimbursement for trips over 15 miles one way (30 miles roundtrip) from home or work location.
• Full training and ongoing support.
• Full curriculum and materials.
• Free chess classes.
• Opportunities for advancement.
• Work flexibility.
• Great company culture.

What This Job Offers

• Job Type: Full-time
• Career Level: Entry Level
• Education Level: No Education Listed