Lead Teacher Trainer I Fall

Chess Wizards • Chicago, IL

18d • Onsite

About The Position

The Lead Teacher Trainer at Chess Wizards teaches chess to elementary students and helps train, develop, coach, and evaluate other instructors. The role models the Chess Wizards experience for students, parents, school administrators, and colleagues, and supports the local Area Manager with program quality, customer service, and operational challenges. The position is based in Chicago, Illinois, and requires reliable transportation to reach classes across the metropolitan area. Relocation assistance is not provided.

Classes typically run for one hour, with instructors arriving 15 minutes early for setup and staying until students have been safely dismissed to an authorized adult. A typical paid class period is approximately 90 minutes, including setup, instruction, and post-class responsibilities. Class start times vary, generally following school dismissal between 2:00 p.m. and 4:00 p.m. The role is paid per class, with higher pay for official class times exceeding one hour. Lead Teacher Trainers are first in line for day-camp opportunities during winter, spring, and summer breaks.

The employer provides full training, ongoing support, a complete curriculum, and materials. The application requires a resume detailing relevant experience and completion of a questionnaire about interest in the role, experience with children, and chess-teaching qualifications.

Requirements

• At least 2–3 years of experience working with groups of children through 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, confidently, and in an age-appropriate way.
• Reliable transportation to reach most or all classes in the metropolitan area.
• Availability during after-school hours at least four days per week.
• 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.

Nice To Haves

• Availability five days a week during peak fall, winter, and spring program weeks.
• Experience teaching, tutoring, or working in a classroom setting.
• Availability for day-camp opportunities during winter, spring, and summer breaks.

Responsibilities

• Lead fun, interactive chess classes for groups of 10–15 elementary students.
• Guide activities, keep students engaged, and redirect behavior when needed.
• Set an example of the Chess Wizards experience for children, parents, school administration, and 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 the programming season.
• Speak with school administrators 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.
• Set up before class 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.
• Career advancement opportunities.
• Flexible work schedules.
• Fantastic company culture.

What This Job Offers

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