Jon Meisburg

About Jon Meisburg

I lead AI-driven innovation inside Learning and Development.With 15+ years at Microsoft, Expedia, and Chewy, my work sits at the intersection of L&D, product thinking, and applied AI. I design and build scalable learning and performance systems that improve quality, reduce cost, and accelerate speed to proficiency.At Chewy, I architected and built the Chewy Customer Simulator, an AI-powered roleplay platform that enables agents to practice realistic customer calls and receive instant, rubric-based coaching. What began as a rapid prototype evolved into a production-ready Realtime API application that I designed and implemented, eliminating per-user licensing costs and reducing annual platform spend by over 80 percent while improving Quality Effectiveness and ramp time.Beyond simulation, I build AI systems directly into the learning ecosystem. This includes voice-based coaching experiences, retrieval-constrained SOP navigation tools, and screen-aware performance support prototypes that combine vision models with structured backend logic. My focus is practical agentic system design inside real operational environments, not isolated experiments.I am energized by work at the intersection of AI systems and learning transformation. That next step could take the form of leading AI-enabled L&D as a Director of Learning and Development, or building agent-based systems as an applied AI engineer. In either case, the focus remains the same: turning emerging AI capabilities into intelligent learning and performance experiences that measurably improve how people work.If you are building AI-enabled learning ecosystems or agent-based systems that improve real-world performance, I would welcome the conversation.

Experience

1. Senior Instructional Designer, Ai Enablement

   Chewy

   Oct 2024 — Present · Bellevue, WA, US

   Lead AI enablement strategy within Customer Care Learning & Development, transforming new hire training and live performance support through governed, scalable AI systems aligned to Quality Effectiveness and customer experience outcomes.**AI-Enabled New Hire Led the design and implementation of AI-powered roleplay to standardize practice across high-volume onboarding programs* Built initial prototype and partnered with AI + Data to transition to scalable Realtime API architecture* Presented innovation roadmap at CTO AI Demo Days to influence enterprise AI direction* Shifted onboarding from content-heavy delivery to AI-powered practice and coaching embedded in the Learn, Practice, Apply framework**Embedded AI Coaching at Designed AI-driven reflection and verbal practice experiences delivering personalized feedback to every learner* Integrated voice AI and dynamic feedback directly into core onboarding programs* Created reusable AI components deployable across courses to reduce cost and improve consistency**In-the-Flow Performance Support Designed Chrome-based just-in-time AI support prototype for live agents* Implemented screen-aware guidance and deterministic click support using structured DOM targeting* Engineered retrieval-constrained architecture to ensure responses are grounded in approved business procedures**AI Governance and Capability Built Phoenix SOP Navigator, an internal AI agent enabling policy-accurate SOP retrieval with enforced source citation* Established indexing standards, prompt governance, and documentation guidelines* Co-led AI Lab evaluating build vs buy decisions for AI roleplay platforms* Trained L&D team on applied AI workflows to elevate AI fluency across the functionDriving the evolution of L&D from content production to AI-enabled performance ecosystems that scale coaching, reduce ramp time, and strengthen customer outcomes.

Education

• University of North Florida

  Bachelor, Communication (Advertising)

• University of Washington

  Software Product Management

• Oregon State University

  Postgraduate Degree, Computer Science

• University of North Florida - Coggin College of Business

  Master of Business Administration (M.B.A.)

Skills

• Adobe Photoshop
• Customer Relations
• Learning Management
• E-Learning
• Organizational Learning
• Voice Over
• Microsoft Office
• Project Management
• Storyboarding
• Gamification
• Customer Insight
• Agile Project Management
• Customer Support
• Training
• Customer Satisfaction
• Sharepoint
• Call Centers
• Instructional Design
• Graphic Design
• Teaching
• Illustrator
• Customer Experience
• Video Production
• Motion Design
• Editing
• Multimedia
• Communication Skills
• Social Media Marketing
• Curriculum Design
• After Effects
• Communication
• Photoshop
• Articulate Storyline
• Customer Relationship Management (Crm)
• Public Speaking
• Instructor-Led Training
• Leadership
• Adobe Creative Suite
• Customer Retention
• Blended Learning