Software Trainer - Bridgeway Benefit Technologies

Bridgeway Benefit Technologies is seeking a Software Trainer to join our growing Professional Services organization. In this role, you will create and conduct interactive classes for customers using our proprietary enterprise benefits administration software, which manages benefit fund calculations, eligibility, claims, and pension processing for the Taft-Hartley industry.

This is a high-ownership position where you will take over customer-facing training from our Business Analysts, master a complex, highly configurable product largely independently, and transform that expertise into comprehensive curriculum for both internal and external audiences. You will deliver live virtual training via Microsoft Teams, tailoring your approach to each customer's technical aptitude and workflow.

Note: This is a remote role requiring approximately 25% travel across the U.S. and Canada. East Coast candidates are preferred.

Key Responsibilities

• Own customer-facing training end-to-end, serving as the primary point of contact for all training initiatives.
• Independently learn the core product and specific customer configurations to build and facilitate curriculum for internal teams and external clients.
• Develop and maintain comprehensive training collateral, including hands-on exercises, job aids, quick-reference guides, and process documentation.
• Collaborate with leadership, product managers, and subject matter experts to ensure curriculum reflects product updates, industry shifts, and customer feedback.
• Deliver customer-specific training sessions both virtually and on-site, aligned with individual configurations and skill levels.
• Manage training logistics, schedules, and rollouts across customer accounts.
• Collect and analyze feedback and training metrics to continuously evaluate and improve instructional materials and delivery.
• Advise internal teams and clients on training scope and methodologies for complex implementations.

Requirements

• Minimum of 3 years of experience delivering technology-based training to adult learners and designing software curriculum.
• Bachelor's degree in a related field.
• Proven ability to collaborate effectively with subject matter experts to dissect complex, configurable software architectures.
• Strong technical writing background with experience creating clear job aids, quick-reference guides, and software documentation.
• Exceptional verbal and written communication skills, with confidence presenting to and engaging stakeholders at all organizational levels.
• Proactive, self-directed mindset with a passion for continuous learning and workflow optimization.
• Strong organizational and project management skills to juggle multiple client engagements concurrently.
• Practical experience leveraging generative AI tools (such as Claude and Copilot) to accelerate productivity and content quality.
• Proficiency with Microsoft Office, PowerPoint, and Smartsheet for curriculum creation, presentations, and schedule management.
• Professional certification in training or learning and development (L&D) is preferred.