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Lead Teacher Trainer Winter

Job in Skokie, Cook County, Illinois, 60077, USA
Listing for: Chess Wizards, Inc
Full Time position
Listed on 2026-01-01
Job specializations:
  • Education / Teaching
    After School, Elementary School
Job Description & How to Apply Below
Position: Lead Teacher Trainer I Winter

Overview

Do you love Chess? Do you love teaching and training others? Do you have the ability to impart good sportsmanship to youngsters? Then you have found the perfect job. The Lead Teacher Trainer position at Chess Wizards plays a key role in aligning our instructors' performance with our customers' expectations, serving as a vital stepping stone toward future management opportunities.

Benefits
  • Competitive Pay: $65 - $85 per class (Typical class time is approximately one hour and thirty minutes which includes pre‑class setup, instructional time, and post‑class responsibilities)
  • 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.
Responsibilities
  • Lead fun, interactive chess classes for 10–15 energetic elementary students, guiding activities, keeping students engaged, and redirecting behavior when needed.
  • Assist in the training, development, and coaching of other instructors.
  • Set the example of what the best Chess Wizards experience should be for our 4 customer groups:
    Kids, Parents, School Administration, and Fellow Colleagues, in full alignment with the Chess Wizards Mission Statement.
  • Assist the local Area Manager in ensuring that all our programs and instructors are visited by management for coaching, customer conversations, and quality control.
  • Assist with the training, coaching, and performance evaluation of our instructors.
  • Help troubleshoot and resolve program challenges.
  • Complete class evaluation reports and discuss with their supervisor.
  • Communicate daily during programming season with their supervisor.
  • Speak regularly with school administration and parents during site visits, gather feedback, and assist with customer service and marketing efforts.
  • Maintain standard professional communication best practices.
  • Arrive on time, prepared, and ready to engage students.
Qualifications
  • Minimum of 2–3 years of experience working with groups of children (teaching, tutoring, coaching, camp counseling, or similar).
  • Must be available during after school hours at least 4 days per week; preference for 5 days a week during peak program weeks (fall, winter, spring). Classes are scheduled after each school’s afternoon dismissal bell, typically between 2:00 pm and 4:00 pm.
  • Strong grasp of chess fundamentals. You should be able to clearly and confidently explain piece movement, basic strategy, and simple tactics in an age‑appropriate way.
  • Reliable transportation and ability to reach most or all of our classes in the metropolitan areas.
  • Ability to reach most or all of our classes in the metropolitan areas – reliable transportation is essential.
  • Strong interpersonal skills and the ability to work as part of a team.
Application Requirements
  • Resume:
    Include a resume detailing your relevant experience, including working with children in educational, recreational, or mentoring settings, as well as any teaching, tutoring, or classroom experience.
  • Questionnaire:
    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.
Location Requirement

This position is based in Skokie, IL. Please note that relocation assistance is not provided. Candidates must be currently residing in the area or be willing to relocate at their own expense.

Chess Wizards is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.

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