Lead Classroom Success Educator – 9 Month Contract

Jobtailor; Toronto; Hybrid; CAD 60,000 - 85,000; Full time

Job summary

Jobtailor is seeking an Ontario Certified Teacher to lead Edwin Academy training, schedule live sessions, publish modules, and provide on-demand support to educators across the GTA. You will train Edwin Educators on Edwin, easyCBM, CCAT, and related platforms, coordinate freelance Classroom Success Educators, and tailor presentations for in-person or online delivery.

This role combines instructional leadership with logistics, requiring travel across the GTA, strong communication, and a

Qualifications

• Ontario Certified Teacher
• Experience training, mentoring, or coordinating educators or freelancers is a plus
• Exemplary presentation skills
• Strong time management and multitasking ability
• Customer-focused approach with urgency and results
• Strong attention to detail and communication skills
• Willingness to travel across the GTA for schools
• Ability to present in person and online after hours

Responsibilities

• Own day-to-day operation of Edwin Academy scheduling, live sessions, and support triage
• Lead training for Edwin Educators on Edwin and assessment platforms, presentation techniques
• Deliver and facilitate virtual and in-person training on Edwin, easyCBM, CCAT, and other platforms
• Source, train, schedule, and assign freelance Classroom Success Educators
• Manage custom requests for enterprise board adoptions with Success Leads
• Identify low-usage schools and proactively offer support and PD
• Monitor site-based adoption health scores and improve engagement
• Maintain and update presentation templates to reflect updates and standards
• Support the Edwin Community of Expert Educators and identify super-users
• Organize and manage the Acuity scheduling platform
• Support planning, creation, and production of national live lessons
• Respond to escalated or sensitive teacher inquiries and elevate as needed
• Surface trends from educator interactions and session feedback for reporting and strategy

Skills

Presentation Skills

Time Management

Organization

Verbal Communication

Written Communication

Collaboration

Technology Skills

Freelance Coordination

Platform Management

Education

Ontario Certified Teacher

Tools

Acuity Scheduling Platform

Edwin

EasyCBM

CCAT

Job description

• Own day-to-day operation of the Edwin Academy, including live session and lesson scheduling, self-paced module publishing, and on-demand support triage
• Lead training for Edwin Educators on Edwin and assessment platforms, presentation techniques, troubleshooting, questions, and presentation skills
• Deliver and facilitate virtual and in-person training on Edwin, easyCBM, CCAT, and other platforms
• Source, train, recommend, schedule, and assign freelance Classroom Success Educators
• Manage custom requests for enterprise board adoptions in collaboration with Success Leads
• Identify low-usage schools and proactively offer support, presentations, and professional development
• Monitor site-based adoption health scores and improve engagement and platform usage
• Maintain and update presentation templates to reflect platform updates and educational standards
• Support the Edwin Community of Expert Educators and identify super-users
• Organize and manage the Acuity scheduling platform
• Support planning, creation, and production of national live lessons
• Respond to escalated or sensitive teacher inquiries and elevate as needed
• Surface trends from educator interactions and session feedback for reporting and strategy

Requirements

• Ontario Certified Teacher
• Prior experience training, mentoring, or coordinating other educators or freelancers is an asset
• Passion for connecting and collaborating to share best practices, materials, and learning opportunities
• Exemplary presentation skills
• Strong time management skills and ability to handle multiple tasks and objectives quickly
• Sense of urgency and results-driven, customer-focused approach
• Strong attention to detail
• Strong organization, written, and verbal communication skills
• Strong technology skills
• Own vehicle with ability to travel to schools across the GTA
• Flexibility to occasionally provide presentations in person and online after normal business hours

Core Competencies

Demonstrates expertise in training and mentoring educators, with strong presentation and communication skills. Proficient in managing educational platforms and fostering engagement through effective support and professional development.

Highest-signal resume keywords

• Ontario Certified Teacher
• Training and Mentoring Educators
• Presentation Skills
• Time Management
• Technology Skills

ATS Optimization Keywords

Hard Skills

• Training
• Scheduling
• Platform Management
• Professional Development
• Data Analysis
• Presentation Template Maintenance
• Support Triage
• Engagement Monitoring
• Freelance Coordination
• Acuity Scheduling

Soft Skills

• Collaboration
• Attention to Detail
• Organization
• Verbal Communication
• Written Communication

Certifications & Qualifications

• Ontario Certified Teacher

Industry Keywords

• Educational Standards
• Professional Development
• Community of Expert Educators
• Customer-Focused Approach
• GTA Travel

Tools & Technologies

• Edwin
• EasyCBM
• CCAT
• Acuity Scheduling Platform