[Hiring] Customer Training & Adoption Specialist @Swiftly

Role Description

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.
• 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.
• Lead internal enablement on new products and features
• Develop and deliver comprehensive training sessions for internal teams.
• Collaborate with Product, Marketing, and Sales teams to gather insights.
• Develop and maintain product education and knowledge base resources
• Create resources including training videos, knowledge base articles, and written workflow guidance.
• Leverage AI tools to accelerate content development.
• Design and lead 1:many product education opportunities
• Identify trends in customer challenges and proactively create educational opportunities.

Success Metrics

• Active user rate: % of unique active users engaging with the platform post-training
• Feature adoption rate: % of trained users actively using key features
• Time to adoption: average time for customers to start utilizing core functionalities
• CSAT scores from post-training and post-webinar surveys
• Qualitative feedback from customers to refine and improve training programs

Qualifications

• 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.
• Strong instructional design and curriculum development skills
• Strong content writing skills for product knowledge bases
• Comfortable being recorded for customer education resources
• Familiarity with change management frameworks
• Tech-savvy and experienced with AI tools
• 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
• Familiarity with transit technology or public sector software is a plus

Benefits

• Competitive salary
• Equity compensation for every employee
• Medical, Dental and Vision
• Retirement with Employer Match
• Flexible Spending Account (FSA)
• Home office setup reimbursement
• Monthly cell/internet reimbursement
• Monthly "Be Well" stipend
• Flexible PTO with a recommended minimum
• Flexible work environment
• 16 paid holidays, including holidays in months without US national holidays
• 12 fully paid weeks of leave for childbirth/adoption