Customer Training & Adoption Specialist – SaaS

This is a fully remote position, open to applicants in California.

📋 Description

• Develop a comprehensive training curriculum and change management strategy.

• Create and enhance a dynamic training curriculum customized to the technical proficiency of customers (beginner, moderate, advanced), as well as their department, role, persona, and agency size.

• Design and implement structured change management initiatives based on best practices to assist agencies in transitioning from onboarding to effectively restructuring their workflows around Swiftly — ensuring that staff integrate it as an essential tool for their job functions rather than merely a new system to learn.

• Provide tailored training throughout the customer journey.

• Lead remote and in-person training sessions for transit agencies during implementation (new customers and upsells) in collaboration with Swiftly's Implementation Managers.

• Assist with post-implementation training for current customers in partnership with Account Managers.

• Conduct training sessions that involve creating and presenting materials, guiding users through Swiftly's solutions via live demonstrations, and addressing product-related inquiries ranging from basic to technical — including the impact of underlying data sources and integrations on what customers experience in the platform.

• Facilitate internal training on new products and features.

• Create and deliver detailed training sessions for internal teams — including Implementation Managers, Customer Success Managers, and Account Managers — to ensure a thorough understanding of new products and features.

• Collaborate with Product, Marketing, and Sales teams to gather insights and align on essential messaging, feature benefits, and use cases.

• Serve as a subject matter expert (SME) for new products and features, providing continuous support and clarification to internal teams as necessary.

• Develop and maintain resources for product education and knowledge management.

• Produce materials such as training videos (specific to products, features, or personas), knowledge base articles, and written guides for workflows and standard operating procedures.

• Keep an updated product education library, ensuring that content remains aligned with the evolving features and workflows of Swiftly.

• Utilize AI tools to expedite content creation — drafting, refining, and maintaining training materials, knowledge base articles, and video scripts at scale without compromising quality.

• Create and lead large-scale product education initiatives.

• Design and conduct live webinars and workshops to promote the adoption of new features and best practices.

• Identify trends in customer challenges and proactively develop educational opportunities for broader audiences.

⛳️ Requirements

• Over 3 years of experience in customer training, learning & development, customer success, or a similar field.

• Quick learner — our product is continuously evolving and changes rapidly.

• Comfortable delving into the underlying structure: understanding how data sources like GTFS feeds, AVL systems, and integrations support the product features you are training on. No engineering background is required, but a willingness to learn enough to diagnose basic issues and communicate effectively with technically diverse audiences is essential.

• Strong skills in instructional design and curriculum development, with the ability to customize training for various customer requirements.

• Proficient content writing skills for product knowledge bases.

• Comfortable being recorded for customer educational resources.

• Familiarity with change management frameworks and their application in a SaaS customer environment — particularly in driving behavioral change beyond mere feature awareness.

• Tech-savvy and experienced with AI tools; willing to adopt new tools and eager to establish repeatable, AI-assisted workflows for content creation, training delivery, and curriculum development.

• Experience in conducting in-person and virtual training sessions for technical software platforms.

• Ability to convert complex workflows into clear, engaging educational materials.

• Excellent communication and presentation skills with a customer-focused approach.

• Knowledge of transit technology or public sector software is an advantage.

🏝️ Benefits

• Competitive salary.

• Equity compensation for all employees.

• Medical, Dental, and Vision coverage.

• Retirement plan with Employer Match.

• Flexible Spending Account (FSA).

• Reimbursement for home office setup.

• Monthly reimbursement for cell/internet expenses.

• Monthly "Be Well" stipend.

• Flexible Paid Time Off (PTO) with a recommended minimum.

• Flexible working environment.

• 16 paid holidays, including holidays in months without US national holidays.

• 12 weeks of fully paid leave for childbirth/adoption.