Software Trainer

Accountabilities:

• Own customer-facing training engagements from planning through delivery, serving as the primary point of contact and ensuring each program meets the customer’s needs and objectives.
• Independently learn the enterprise software and individual customer configurations deeply enough to develop and facilitate effective training, becoming a trusted product subject matter expert.
• Create and maintain engaging training materials, including exercises, job aids, quick-reference guides, presentations, and process documentation for technical and non-technical audiences.
• Deliver interactive training virtually and on-site, adapting teaching methods and content to each customer’s configuration, skill level, technical aptitude, and learning needs.
• Collaborate with leadership, product managers, and subject matter experts to keep training curricula aligned with product updates, industry developments, and customer feedback.
• Manage training schedules and deployments across multiple customer accounts while maintaining strong organization and communication throughout each engagement.
• Collect feedback and performance data from training sessions and use those insights to continuously improve content, curriculum, and delivery approaches.
• Consult with customers and internal stakeholders on training scope, methodology, and execution for projects involving unique or complex requirements.

Requirements:

• Bring at least 3 years of experience delivering technology-based training to adult learners and developing structured learning curricula.
• Hold a bachelor’s degree in a related field, with formal training or learning-and-development certification considered an advantage.
• Demonstrate the ability to work effectively with subject matter experts and learn complex, configurable software across varied customer environments.
• Have strong technical writing skills and experience creating clear job aids, quick-reference guides, process documentation, and other materials for software or technical audiences.
• Possess excellent written, verbal, presentation, and facilitation skills, with the ability to explain complex software functionality clearly and engage learners at different organizational levels.
• Be proactive, self-motivated, and comfortable working independently, with a genuine interest in continuous learning, process improvement, and enhancing the customer experience.
• Demonstrate strong organizational and project management skills, with the ability to manage multiple training engagements and priorities simultaneously.
• Have experience using generative AI tools such as Claude and Copilot to improve productivity and produce high-quality outcomes.
• Be familiar with Microsoft Office, PowerPoint, and Smartsheet for developing training materials, presentations, and managing training schedules.

Benefits:

• Fully remote position based in Canada.
• Approximately 25% travel across the U.S. and Canada, providing opportunities for both virtual and on-site customer engagement.
• Opportunity to become a product subject matter expert while working with complex enterprise software and diverse customer environments.
• High-ownership role with significant autonomy over customer training, curriculum development, and continuous improvement.
• Exposure to professional services, enterprise technology, customer enablement, and benefits administration processes.
• Collaboration with product leaders, subject matter experts, and customer-facing teams in a dynamic technology environment.
• Opportunities to leverage generative AI and modern productivity tools to enhance training development and delivery.
• East Coast candidates are preferred.