Software Trainer

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Software Trainer based in Canada. This role offers the opportunity to become a subject matter expert in a complex, highly configurable enterprise benefits administration platform. You’ll own customer-facing training from end to end, transforming detailed product knowledge into engaging learning experiences for both internal teams and external customers. The role combines independent learning, curriculum development, live virtual instruction, and customer consultation. You’ll tailor training to different configurations, technical abilities, and organizational needs while partnering with product leaders and subject matter experts. With significant ownership and approximately 25% travel across the U.S. and Canada, this is a strong fit for someone who enjoys technology, teaching, continuous improvement, and customer impact.

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.

How Jobgether Works We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

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