Software Trainer

Bridgeway Benefit Technologies is seeking a Software Trainer to join our growing Professional Services organization. This remote position requires approximately 25% travel within the U.S. and Canada, with a strong preference for East Coast candidates.

About the role

As a Software Trainer, you will create and conduct interactive classes for our customers using our proprietary enterprise benefits administration software. This software handles the calculation and processing of benefit funds, eligibility, claims, and pensions for the Taft-Hartley industry. You will become a product subject matter expert while contributing to eLearning content development and collaborating with all levels of the business to enhance the customer experience.

We're looking for a driver to take real ownership of customer-facing training, allowing our Business Analysts to focus on core analysis and configuration work. This role requires confidence in learning a complex, highly configurable product independently, building genuine expertise, and developing a training curriculum for both internal teams and external customers. The ideal candidate thrives in ambiguous situations and adapts to the unique configurations of our clients' software environments.

Responsibilities

• Take full ownership of customer-facing training, serving as the primary point of contact for all training engagements.
• Proactively learn the software’s functionality and complexity, including customer-specific configurations, to independently build and facilitate training curricula for internal and external audiences.
• Develop and maintain training materials, including e-learning modules, exercises, job aids, quick-reference guides, and process documentation.
• Collaborate with leadership, product managers, and subject matter experts to enhance the curriculum based on industry trends, customer feedback, and software updates.
• Train new customers on software usage, both virtually (via Teams/Zoom) and on-site across the U.S.
• Consult with customers and internal teams to plan, develop, and deliver tailored training programs based on specific software configurations or project needs.
• Manage customer training schedules and deploy sessions for various accounts.
• Facilitate interactive, engaging, and effective training sessions tailored to the Taft-Hartley industry.
• Monitor user progress and gather feedback to refine training content and delivery methods.
• Continuously update personal knowledge of Taft-Hartley practices to ensure training content remains relevant.
• Evaluate training effectiveness using metrics and best practices.
• Contribute to eLearning content development as a product subject matter expert.
• Act as a solutions-oriented self-starter with a passion for improving processes, documentation, and the customer experience.
• Collaborate with cross-functional teams to achieve business goals.

Requirements

• Minimum of 3 years of experience delivering technology-based training to adult learners and developing curriculum.
• Bachelor’s degree in a related field or strong knowledge of instructional design techniques.
• Proven experience as a software trainer with a passion for continuous learning and professional growth.
• Ability to thrive in ambiguous situations and make sound judgment calls given the complexity and configurability of the software.
• Confidence to independently learn a complex product and translate that knowledge into a training curriculum for diverse audiences.
• Technical writing skills, with experience producing clear job aids, quick-reference guides, and process documentation.
• Self-starter mindset with a genuine passion for improving processes, not just documenting them as-is.
• Experience in the Taft-Hartley industry and with enterprise-class software solutions is preferred.
• Certification in training or learning and development is preferred.
• Strong written and verbal communication, presentation, and problem-solving skills.
• Ability to engage with individuals at all levels of an organization.
• Proactive, self-motivated, organized, reliable, and outgoing with a passion for tackling challenges.
• Familiarity with modern training methods, tools, and techniques.
• Exceptional ability to convey complex software functionalities in a clear and concise manner.
• Strong organizational skills to manage multiple training sessions simultaneously.
• Ability to work both independently and collaboratively with cross-functional teams.

Schedule

This is a remote position with approximately 25% travel within the U.S. and Canada.