Customer Training & Adoption Specialist(SaaS)

Swiftly, Inc.•British Columbia, ON

3d•$105,400 - $124,000•Remote

About The Position

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.

Requirements

3+ years of experience in customer training, learning & development, customer success, or a related role
Quick learner — our product is ever-evolving and changes fast
Comfortable going a layer beneath the UI: understanding how data sources like GTFS feeds, AVL systems, and integrations power the product features you're training on. You don't need to be an engineer, but you're willing to learn enough to diagnose basic issues and speak credibly to technically diverse audiences.
Strong instructional design and curriculum development skills, with the ability to tailor training to diverse customer needs
Strong content writing skills for product knowledge bases
Comfortable being recorded for customer education resources
Familiarity with change management frameworks and how to apply them in a SaaS customer context — particularly in driving behavioral change, not just feature awareness
Tech-savvy and experienced with AI tools; comfortable adopting new tools and eager to develop repeatable, AI-assisted workflows for content creation, training delivery, and curriculum development
Experience conducting in-person and virtual training sessions for technical software platforms
Ability to translate complex workflows into digestible, engaging educational content
Excellent communication and presentation skills with a customer-centric mindset

Nice To Haves

Familiarity with transit technology or public sector software is a plus

Responsibilities

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.