Lead Teacher Trainer I Fall

Chess Wizards • Chicago, IL

20d • $65 - $85 • Onsite

About The Position

The Lead Teacher Trainer at Chess Wizards helps align instructors’ performance with customer expectations and is a stepping stone toward future management opportunities. In addition to teaching as a top instructor, the role assists with training, developing, coaching, and evaluating other instructors.

Lead fun, interactive chess classes for groups of 10–15 elementary students, helping students stay engaged and redirecting behavior when needed. The role also supports the local Area Manager with program visits, coaching, customer conversations, quality control, troubleshooting, and resolving program challenges. Lead Teacher Trainers communicate regularly with their supervisor and with school administrators and parents during site visits, gathering feedback and supporting customer service and marketing efforts.

The position is based in Chicago, Illinois. Work is primarily during after-school hours, with availability required at least four days per week and a preference for five days during peak fall, winter, and spring program weeks. Class schedules depend on available programs; most classes begin between 2:00 p.m. and 4:00 p.m. Teachers arrive 15 minutes before class and stay until students are safely dismissed to an authorized adult. Classes are paid per class, typically for approximately 1.5 hours including setup, instruction, and post-class responsibilities. Longer official class times are paid at a higher rate. Lead Teacher Trainers are also the first scheduling choice for day camps during winter, spring, and summer breaks.

Chess Wizards provides full training and ongoing support, a complete curriculum and materials, free chess classes, career advancement opportunities, flexible work schedules, and a company culture described as fantastic. Relocation assistance is not provided; candidates must live in the area or relocate at their own expense.

Requirements

• At least 2–3 years of experience working with groups of children, such as teaching, tutoring, coaching, camp counseling, or similar work.
• Strong grasp of chess fundamentals, including the ability to explain piece movement, basic strategy, and simple tactics clearly and confidently in an age-appropriate way.
• Reliable transportation to reach classes across metropolitan areas.
• Availability during after-school hours at least four days per week.
• Must currently reside in the Chicago area or be willing to relocate at personal expense.
• Submit a resume detailing relevant experience working with children and any teaching, tutoring, or classroom experience.
• Complete the required application questionnaire about interest in the role, experience working with children, and qualifications to teach chess.

Nice To Haves

• Availability five days a week during peak fall, winter, and spring program weeks.

Responsibilities

• Lead fun, interactive chess classes for 10–15 elementary students.
• Guide activities, engage students, and redirect behavior when needed.
• Set an example of the Chess Wizards experience for children, parents, school administration, and fellow colleagues, in alignment with the company mission.
• Assist the local Area Manager in ensuring programs and instructors receive management visits for coaching, customer conversations, and quality control.
• Assist with training, coaching, and performance evaluation of instructors.
• Help troubleshoot and resolve program challenges.
• Complete class evaluation reports and discuss them with the supervisor.
• Communicate daily with the supervisor during programming season.
• Speak regularly with school administration and parents during site visits, gather feedback, and assist with customer service and marketing efforts.
• Maintain professional communication best practices.
• Arrive on time, prepared, and ready to engage students.
• Arrive 15 minutes before class to set up and prepare, and remain until students are safely dismissed to an authorized adult.

Benefits

• Competitive pay of $65–$85 per class.
• Mileage reimbursement for trips over 15 miles one way (30 miles roundtrip) from home or work location.
• Full training and ongoing support.
• Access to a complete curriculum and materials.
• Free chess classes.
• Opportunities for career advancement.
• Flexible work schedules.
• Company culture described as fantastic.

What This Job Offers

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