Customer Training & Adoption Specialist(SaaS)

About the Professional Services Team

The Professional Services team is part of the broader Customer Success department at Swiftly, working to ensure customers are happy and finding immense value in the tools that Swiftly provides.

The Customer Success department comprises Implementation Managers, Account Managers, and Technical Support Representatives. This department is on the front line — the first point of contact for customers who have questions, are encountering issues, or need support during the implementation phase of our relationship. When problems arise, we ensure that individual customers are heard and that their issues are cared for, and we apply a keen analytical eye to spot trends and communicate problems proactively with the product team. We are passionate about improving mobility in the communities we serve, and we work side by side with transit agencies and operators to ensure their projects are impactful. We love the human aspect of our work and thrive on getting creative to solve problems or boost network performance. The Customer Success org is responsible for everything post-sale, and the Implementations team is a critical part of starting our customers on the right foot.

About the Role

Reporting to Stan Parkford, the Customer Training and Adoption Specialist will be responsible for designing, delivering, and evolving customer training programs to enhance adoption and proficiency across our customer agencies. You'll create dynamic, role-based learning experiences, provide personalized training sessions, and develop scalable educational resources to support users at every stage of their journey — from pre-sales through implementation to ongoing education. Central to this work is structured change management: helping agencies reorient their teams around optimized workflows and realize the full value of Swiftly as a core part of how they do their jobs.

This role will work closely with Implementation Managers, Account Managers, Solutions Engineers, and Product Managers.

This is a remote position that will require frequent travel — 8 to 14 trips per year are expected.

What You'll Do

Create a dynamic training curriculum and change management program

• Develop and refine a dynamic training curriculum tailored to customers' technical aptitude (beginner, moderate, advanced), department, role, persona, and agency size.
• Design and execute structured change management programs grounded in best practices, helping agencies move beyond onboarding to genuinely reorienting their workflows around Swiftly — so staff adopt it as a core tool for their job functions, not just a new system to learn.

Deliver personalized training across the customer journey

• Lead remote and on-site training for transit agencies during implementation (new customers and upsells) in coordination with Swiftly's Implementation Managers.
• Support post-implementation training for existing customers in collaboration with Account Managers.
• Training sessions include creating and presenting materials, guiding users through Swiftly's solutions via live demonstrations, and answering product-related questions ranging from basic to technical — including how underlying data sources and integrations affect what customers see in the platform.

Lead internal enablement on new products and features

• Develop and deliver comprehensive training sessions for internal teams — including Implementation Managers, Customer Success Managers, and Account Managers — to ensure deep understanding of new products and features.
• Collaborate with Product, Marketing, and Sales teams to gather insights and align on key messaging, feature benefits, and use cases.
• Act as a subject matter expert (SME) for new products and features, providing ongoing support and clarification to internal teams as needed.

Develop and maintain product education and knowledge base resources

• Create resources including (but not limited to): training videos (product-, feature-, or persona-specific), knowledge base articles, and written workflow and standard operating procedure guidance.
• Maintain an up-to-date product education library, ensuring content aligns with evolving Swiftly features and workflows.
• Leverage AI tools to accelerate content development — drafting, refining, and maintaining training materials, knowledge base articles, and video scripts at scale without sacrificing quality.

Design and lead 1:many product education opportunities

• Design and facilitate live webinars and workshops to drive adoption of new features and best practices.
• Identify trends in customer challenges and proactively create educational opportunities for broader audiences.