Assistant Chess Instructor Fall

Chess Wizards, Inc.; Boylston (MA); On-site; USD 34,440 - 48,216; Full time

Benefits offered by this job

Full training and ongoing support

Free chess classes

Opportunities for advancement to Chess

Work flexibility

Great company culture

Job summary

Chess Wizards, Inc. seeks enthusiastic Assistant Instructors to support our after-school chess program for elementary students in Boylston, MA. You will assist the instructor, manage a dynamic class, and help students practice chess fundamentals in a fun, structured setting.

The role offers hands-on teaching experience with a flexible schedule (1–5 classes/week) and mileage reimbursement for travel between local schools. Training and materials are provided to ensure confident classroom support.

Qualifications

• Genuine interest in working with groups of elementary students.
• Experience (teaching, tutoring, camp counseling, or similar) is a plus.
• Ability to follow direction and support classroom management.
• Professional, positive, and kid-friendly demeanor.
• Desire to be a positive role model and promote good sportsmanship.
• Strong grasp of chess fundamentals and ability to explain moves and basic tactics.
• Ability to connect chess problem-solving to real-life problem-solving.
• Reliable personal transportation and ability to drive between locations.
• Availability on weekday afternoons (2:00 PM–5:00 PM) to teach 1–5 classes per week.
• Commitment to school safety protocols and punctuality.

Responsibilities

• Assist the Chess Instructor in setting up and managing a 15–22 student class.
• Provide one-on-one or small-group support to help practice piece movements and concepts.
• Support activities, keep students engaged, reinforce good behavior.
• Follow the curriculum and promote sportsmanship with the instructor.
• Maintain a lively, positive classroom environment.
• Encourage problem-solving, creativity, and critical thinking.
• Follow school safety protocols during arrival, dismissal, and activities.
• Travel to various local school sites for sessions.
• Arrive prepared and ready to engage students.

Skills

Teaching

Tutoring

Camp counseling

Kid-friendly demeanor

Job description

Area: Boylston, MA

Do you love chess? Do you enjoy working with kids?

Chess Wizards is seeking enthusiastic, reliable Assistant Instructors to support our after-school enrichment program! This is a perfect opportunity to develop teaching skills, learn effective classroom strategies, and share the magic of chess with young students. Join our team and get paid to mentor future chess players!

Why Join Us?

• Competitive Pay: $25 - $35 per class (Typical class time is approximately one hour and thirty minutes which includes pre-class setup, instructional time, and post-class responsibilities)
• Flexible Hours: Teach a minimum of 1 class up to a maximum of 5 classes per week. The specific number is based on the availability of classes at local schools in your area. Classes are scheduled on weekday afternoons, with start times typically falling between 2:00 PM and 5:00 PM at various local schools
• 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.
• Skill Development: Excellent opportunity to gain hands‑on teaching experience

What You'll Do

• Assist the Chess Instructor in setting up and managing a fun, interactive chess class for 15-22 elementary students.
• Provide one-on-one or small-group support to students, helping them practice piece movements and understand basic concepts
• Support the Chess Instructor in guiding activities, keeping students engaged, and reinforcing positive behavior.
• Follow the structured curriculum and promote good sportsmanship alongside the Chess Instructor.
• Manage a lively classroom with confidence and positivity
• Encourage problem‑solving, creativity, and critical thinking
• Follow school safety protocols, including supervision 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

What We're Looking For

Required

• Genuine interest in working with groups of elementary students.
• Experience (teaching, tutoring, camp counseling, or similar) is a plus
• Ability to follow direction, support the Chess Instructor's classroom management, and help create interactive, friendly, and fun sessions. We seek upbeat, engaging assistants who are eager to support the learning environment.
• Professional, positive, and kid‑friendly demeanor
• Genuine desire to be a positive role model and promote good sportsmanship
• 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.
• Ability to connect chess problem‑solving to real‑life problem‑solving
• Reliable personal transportation and the ability to drive between locations.
• Availability on weekday afternoons, with class start times falling within the 2:00 PM to 5:00 PM window, to teach 1-5 classes per week. The specific number of classes depends on availability at local partner schools.
• Commitment to implementing school safety protocols to protect students' well‑being. Because you will supervise children, a strong record of reliability and strict adherence to safety and school policies is required.
• Strong punctuality and time‑management skills

Application Requirements

• 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

Chess Wizards Assistant Instructors receive: Full training and ongoing support. Full curriculum and materials. Free chess classes. Opportunities for advancement to Chess Instructor. Work flexibility. Great company culture!

Location Requirement: This position is based in Boylston, MA. 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.