Training Operations Lead
About CultureAlly
CultureAlly is a fast-growing workplace culture and training company. We partner with leading organizations across North America to deliver impactful training, consulting, and eLearning experiences that elevate workplace culture and drive meaningful organizational change. We’re expanding our Learning & Development team and are hiring a dedicated Training Operations Lead to support our company through the next phase of growth.

Role Overview
As the Training Operations Lead , you will play a critical role in ensuring the smooth, efficient, and scalable delivery of CultureAlly’s training experiences. Reporting to the Director of Learning & Development , you will lead all operational logistics related to training experience delivery – including scheduling, facilitator coordination, client communication, training content adjustments, contractor (facilitator and technical producer) hiring and forecasting, and Asana project management monitoring and reporting. You will directly manage and coach a Training Coordinator , ensuring high-quality support across the training lifecycle.

You’ll partner closely with Learning & Development, Sales, Product & Marketing, and Finance teams to improve workflows, optimize processes, and maintain accurate forecasting and reporting. This role requires a detail-oriented operations professional with robust project management experience, excellent leadership and communication skills, and the ability to manage complex logistics in a fast-paced environment.

What You’ll Do
As the Training Operations Lead , you will be a “player/coach” and will perform the duties of the roles you are leading and supporting as needed, including but not limited to:

Technical production of live virtual training sessions

Post session materials follow-up (recordings, takeaway resources, etc.)

Training session facilitation

Content development and deck building

Additional responsibilities will include:

Training Operations & Scheduling

Coordinate and schedule all training experiences, ensuring that every purchased program is assigned a delivery date





Communicate directly with clients to confirm scheduling details and follow up proactively to book any outstanding sessions

Schedule internal and external facilitators, ensuring alignment between facilitator expertise, availability, and client needs

Arrange facilitator travel and secure necessary budget approvals

Facilitator & Contractor Management

Source, hire, and onboard contract facilitators, ensuring availability, expertise, and First-Voice perspectives align with training experience needs

Maintain accurate and up-to-date facilitator records, including bios, areas of expertise, availability, and rates

Manage contractor budgets and training-related spend, ensuring adherence to approved rates and guidelines

Lead monthly and quarterly forecasting for facilitator and technical producer spend

Maintain weekly reporting that compares actuals vs. forecast and highlights variances or risks

People Leadership

Lead, coach, and develop 1-2 direct reports, currently a Training Coordinator

Provide clear guidance, feedback, and professional development support to ensure strong performance and efficiency

Delegate tasks effectively and manage workload distribution for operational excellence

Conduct regular Performance & Development conversations, inclusive of Year End Reviews

Provide direction and feedback, as appropriate, to contract facilitators and technical producers and escalace any concerns to the Director of Learning & Development

Process Improvement & Cross-Functional Collaboration

Identify opportunities to improve operational processes, systems, and documentation

Implement process improvements to enhance scalability, consistency, and cross-team workflow

Partner across L&D;, Sales, Product & Marketing, and Finance to ensure smooth handoffs, accurate reporting, and consistent client experiences





Provide minor client consultation and make light content edits for Off-the-Shelf (OTS) training programs as needed

Reporting, Tools & Data Management

Utilize Asana (or other project management tools) to manage timelines, assignments, and cross-functional visibility

Leverage Google Sheets/Excel for forecasting, budget tracking, P&L; reporting, and operational dashboards

Monitor key operational metrics and elevate issues or risks proactively

Ensure documentation of processes, templates, and workflows is regularly updated and optimized

You Should Have

2+ years of experience leading at least one direct report

Experience with labour scheduling, workforce planning, or training operations

Experience with data analytics and reporting (P&Ls;, budgets, financial tracking)

Strong project management experience, ideally using Asana or similar tools

High level of detail orientation and operational rigor

Strong written and verbal communication skills, including client-facing communication

Proficiency with Google Slides/PowerPoint

Advanced proficiency with Google Sheets/Excel

Ability to manage complex logistics, competing priorities, and multiple stakeholders

Comfort collaborating across multiple business functions

Proficiency with Google Slides/PowerPoint and virtual meeting platforms (ex. Zoom)

Strong project management, time management, and stakeholder engagement capabilities

Excellent written and verbal communication skills, including strong presentation and facilitation abilities

Nice to Have

Bilingual in English/French

Knowledge of DEI practices and workplace culture strategy

Experience leveraging AI tools to increase efficiency and workflow automation

Compensation & Benefits

Total Compensation: $85,000–$95,000 CAD

Comprehensive health and dental benefits

3 weeks vacation + 3 flexible cultural/personal leave days

Career growth opportunities within a mission-driven, growing organization

Other Details

Fully remote role based in Canada

Standard hours: 9 a.m. – 5 p.m. EST (flexibility required for client scheduling)

Travel as needed for team/company meetings within North America may be required

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📌 Training Operations Lead (Remote) (Ontario)
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📍 Ontario