Training Operations Lead

CultureAlly Software Inc.; California (MO); Hybrid; USD 61,000 - 68,000; Full time

Benefits offered by this job

Health benefits

Vacation & leave

Career growth

Job summary

CultureAlly Software Inc. is seeking a Training Operations Lead to orchestrate the end-to-end delivery of our training experiences. You’ll oversee scheduling, facilitator coordination, client communication, and forecasting, while coaching a Training Coordinator.

Based remotely in Canada, you will partner with Learning & Development, Sales, Product & Marketing, and Finance to improve workflows, report on performance, and ensure scalable operations in a fast-growing environment.

Qualifications

• 2+ years leading at least one direct report.
• Experience with labour scheduling or training operations.
• Experience with data analytics and reporting (P&L, budgets).
• Strong project management experience using Asana or similar tools.
• Excellent communication and stakeholder engagement skills.

Responsibilities

• Coordinate and manage training experiences, dates, and speaker alignment.
• Forecast facilitator and contractor spend; manage budgets and costs.
• Coach and develop a Training Coordinator and other teammates.
• Improve cross-functional workflows with L&D, Sales, Product, Marketing, and Finance.
• Maintain dashboards and reporting for performance and risk visibility.

Skills

People leadership

Project management

Data analytics

Budget forecasting

Google Sheets

Excel

Communication

Client facing

Scheduling

Stakeholder management

Tools

Asana

Google Sheets

Excel

PowerPoint

Job description

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 strong 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 elevate 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 escalating 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