Software Trainer

Bridgeway Benefit Technologies is seeking a Software Trainer to join our growing Professional Services organization. As a Software Trainer, you will be responsible for creating and conducting interactive classes for our customers using our proprietary enterprise benefits administration software. The software manages benefit fund calculations, eligibility, claims, and pension processing for the Taft-Hartley industry.

This is a high-ownership role - you’ll take over customer-facing training from our Business Analysts, learning a complex, highly configurable product largely on your own and turning that expertise into curriculum for internal and external audiences.

You’ll deliver live virtual training via Teams, adapting your approach to each customer’s skill level and technical aptitude.

This is a remote position with about 25% travel across the U.S. and Canada; East Coast candidates are preferred., * Own customer-facing training end to end, acting as the primary point of contact for all training engagements.

• Independently learn the product and each customer’s configuration well enough to build and facilitate curriculum for internal teams and external customers, becoming a product subject matter expert.
• Develop and maintain training materials - exercises, job aids, quick-reference guides, and process documentation.
• Collaborate with leadership, product managers, and subject matter experts to keep the curriculum current with product changes, industry trends, and customer feedback.
• Deliver customer-specific training, virtually and on-site, tailored to each customer’s configuration and skill level.
• Manage training schedules and deployment across customer accounts.
• Gather feedback and performance data from training sessions and use it to continuously evaluate and refine content and delivery methods.
• Consult with customers and internal teams on training scope and approach for projects with unique or complex requirements.

• A minimum of 3 years of experience delivering technology-based training to adult learners and developing curriculum.
• A bachelor’s degree in a related field.
• Able to partner with subject matter experts, given the complexity and configurability of the software and range of customer environments.
• Technical writing skills, with experience producing clear job aids, quick-reference guides, and process documentation for a technical or software audience.
• Strong written and verbal communication and presentation skills, with the ability to convey complex software functionality clearly and engage individuals at all levels of an organization.
• A proactive, self-motivated self-starter with a genuine passion for continuous learning and for improving processes and the customer experience, not just documenting them as-is.
• Strong organizational skills, with the ability to manage multiple training engagements simultaneously.
• Certification in training or learning and development is preferred.
• Experience using generative AI tools such as Claude and Copilot to improve productivity and deliver high-quality outcomes.
• Familiarity with Microsoft Office, PowerPoint, and Smartsheet for developing training materials, presentations, and managing training schedules.