Rich Skinner

AI Enablement Specialist

Wilmington, DE | Portfolio | Email | LinkedIn | GitHub

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Professional Summary

I turn emerging AI capabilities into scalable enablement—bridging technical innovation, instructional design, and organizational readiness to accelerate adoption and measurable impact. My work spans generative AI simulations, enterprise methodology training, and technical onboarding reaching tens of thousands of learners globally.

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Core Competencies

AI & Learning Innovation: Prompt engineering, LLM evaluation design, conversational AI integration, simulation-based learning

Instructional Design: Scenario-based learning, assessment design, video production, accessibility implementation, SCORM development

Enterprise Enablement: Cross-functional program leadership, stakeholder collaboration, change management, global deployment

Technical Platforms: Second Nature AI, Azure OpenAI Service, Microsoft Copilot, Articulate 360, Intrepid, Seismic, Viva Learning

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Professional Experience

Senior Instructional Designer

Microsoft (via GP Strategies Corporation) | April 2022 - July 2025 | Remote

AI & Innovation

• Pioneered first enterprise deployment of generative AI role-play simulations for technical sales validation, designing conversational AI personas with realistic objections and automated capability assessment
• Integrated Bongo AI conversational assistant into Azure Cloud Architect training, enabling personalized learning guidance at scale without human facilitators
• Achieved 25% efficiency improvement in assessment creation through Copilot-assisted workflows, eliminating legacy bottlenecks while maintaining quality standards
• Led internal sessions on AI-powered simulations and prompt engineering, rated "ten out of ten" by program leadership

Enterprise-Scale Enablement

• Enabled 62,000+ global learners through Microsoft Customer Engagement Methodology training, standardizing practices across sales, technical, and customer success roles
• Reduced average time-to-productivity by 20% for Security division new hires through comprehensive 120-day onboarding program with role-specific capability validation
• Reached 11,000+ learners through short-form video enablement series supporting onboarding and security programs across Modern Work and Security segments

Cross-Functional Program Leadership

• Co-developed role-specific enablement operationalizing customer engagement methodology across Account Executive, Solution Specialist, and Customer Success Manager roles
• Partnered with subject matter experts, product teams, and field stakeholders ensuring content accuracy and strategic alignment with FY24-25 priorities
• Contributed to user acceptance testing for sales process tooling, providing feedback that improved field usability and adoption

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Global Learning Experience Designer

Meta | November 2021 - February 2022 | Remote

• Designed multi-modal training for Reality Labs products (Meta Quest 2, Ray-Ban Stories, Portal) supporting Meta Store retail and field sales teams
• Created safety, security, and leadership training programs including eCourses, activity guides, workbooks, and device learning labs
• Built product demo experiences and customer engagement training for consumer electronics launch
• Collaborated cross-functionally with product, operations, and field sales teams on global learning strategy

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Training Lead

Microsoft | June 2020 - July 2021 | Remote

• Led and developed a team of trainers delivering customized sessions on the Microsoft 365 platform across enterprise, government, and education environments
• Collaborated with Microsoft account teams, customer IT/business enablement teams, and end-users ensuring successful implementation of modern workplace solutions
• Designed and facilitated training programs supporting digital transformation initiatives during remote work acceleration

Learning Specialist

Microsoft | November 2013 - June 2020 | Newark, Delaware

• Developed in-store training, onboarding, and career development programs supporting retail operations
• Led product launch enablement for Windows, Office, Surface, and Microsoft 365 across multiple release cycles
• Earned Microsoft MVP Awards (February 2015, July 2016, October 2017, October 2018) for learning innovation
• Received WOW of the Week Winner recognition (November 2016) for exceptional customer engagement training

Content Developer (Concurrent Role)

Microsoft | March 2017 - August 2019

• Supported digital transformation of training materials and evaluated efficacy in achieving learning goals
• Created and updated courses based on current and future learning priorities across the organization
• Proofed digital assets for branding and messaging consistency

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Education

High School Diploma

Bel Air High School | 2004-2007

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Certifications

• Microsoft Certified: Azure Fundamentals
• Microsoft Certified: Dynamics 365 Fundamentals
• Microsoft Certified: Power Platform Fundamentals
• Microsoft 365 Certified: Fundamentals
• Microsoft Innovative Educator
• Microsoft Office Specialist: PowerPoint 2016
• Microsoft Office Specialist: Word Expert 2016

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Technical Proficiencies

AI & Automation: Second Nature, Azure OpenAI Service, Microsoft Copilot, Prompt Engineering, LLM Evaluation

Learning Design Tools: Articulate Storyline 360, Articulate Rise 360, Adobe Creative Suite, Camtasia, Clipchamp, Vocal Video

Platforms & Systems: Intrepid, Seismic, Viva Learning, SharePoint, Adobe Experience Manager, Mural, Figma

Collaboration & Productivity: Microsoft 365, Teams, Workplace by Meta, Asana, Zoom

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Key Achievements

• 62,000+ global learners enabled through customer engagement methodology training
• AI simulation pioneer: First enterprise deployment of generative AI role-play for technical capability validation
• 25% efficiency improvement in assessment creation through AI-assisted workflows
• 20% faster onboarding for Security new hires through a 120-day capability-focused curriculum
• Executive visibility through AI-assisted simulation pilots and demos informing program strategy