Customer Education Specialist, Financial Technology - Chicago

Role Overview The Customer Education Specialist is responsible for designing, developing, and delivering scalable training programs and product education initiatives that drive user understanding, feature adoption, and overall client success. This role works cross-functionally with Product, Service/Support, and Marketing teams to translate complex platform functionality into clear, engaging, and user-focused training experiences and resources. The ideal candidate is equal parts educator, content strategist, and product translator—someone who can turn complexity into clarity at scale. Key Responsibilities Training Programs & Delivery Support the development of scalable training initiatives, including webinars, structured learning programs, and other one-to-many education efforts Continuously evaluate and improve training programs based on engagement metrics and user feedback Facilitate and moderate live training sessions, workshops, webinars, and other training outlets as needed Content Development & Strategy Create and maintain high-quality product education content across formats, including video, written documentation, and live training materials Ensure consistency in messaging, tone, and accuracy across all training and content resources Contribute to the evolution and scalability of training programs and content strategies Product Collaboration & Enablement Partner closely with Product teams to support feature launches through training, documentation, and user-facing communications Translate complex workflows and functionality into clear, actionable, and user-friendly content Provide feedback to Product teams based on user interactions, training sessions, and identified documentation gaps Systems & Process Improvement Identify and recommend improvements to systems and processes that enhance training delivery and user engagement Drive efficiencies and scalability across training and enablement initiatives Help implement tools or workflows that improve content creation and distribution Knowledge Base & Documentation Own and continuously improve the Knowledge Base and training documentation Ensure all resources are accurate, up-to-date, and aligned with product updates Optimize documentation to promote user self-service and reduce support dependency Cross-Functional Support Serve as a subject matter resource for Service, Support, and Product teams on training materials and platform functionality Support internal enablement initiatives and help bridge communication between product development and user experience Collaborate across teams to ensure alignment in how the platform is presented and understood Qualifications 3+ years of experience in training, product education, customer enablement, or a related role in finance (CFP or financial designation a plus) Experience creating multi-format educational content (video, written, live sessions) Strong ability to simplify complex concepts into clear, user-friendly materials Experience working cross-functionally with Product, Marketing, and Customer Success teams Excellent communication, presentation, and facilitation skills Strong organizational skills with the ability to manage multiple projects simultaneously Familiarity with learning management systems (LMS), knowledge base tools, or content platforms is a plus Preferred Skills Experience in SaaS, fintech, or platform-based products Data-driven mindset with the ability to use metrics to improve training effectiveness Comfort with webinar tools, video creation software, and documentation platforms Experience supporting product launches or feature rollouts Impact & Success Metrics Increased adoption of product features and core workflows Improved effectiveness and scalability of training programs and documentation Reduced support burden through enhanced self-service resources Strong alignment across Product, Service/Support, and Training teams Targeting a $65-$75k base, and a 15 to 25% bonus target This is a remote position within the approved states.