Learning Strategy · AI Enablement · Workforce Transformation

I turn learning, technology, and strategy into better ways of working.

I'm Joshua Luna, an L&D and AI enablement leader who builds workforce capability, drives adoption, and turns complex change into measurable business results.

Harvard Business ReviewPublished author

The Toxic Effects of Branding Your Workplace a “Family”

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Recognized in Leadership

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Teachable Moments4,100+

Readers learning practical leadership frameworks

Uber · Salesforce · Deloitte · PwC

Career progression

13+ years from performance training to enterprise AI enablement.

The scope grew from a 12-person sales team to regions, global employee populations, AI products, and an enterprise roadmap for about 22,000 employees.

2026 to now

PayPal

Enterprise AI Enablement Leader

3 AI tools + measured adoption

2023 to 2026

Mgmt On-Demand

Head of Learning & Development

AI coach + learning product

2019 to 2023

Numerator

Learning & Development Consultant

2,500 employees + 59 NPS

2018 to 2019

RE/MAX INTEGRA

Learning & Development Trainer

+247% sales-agent volume

2016 to 2017

Coldwell Banker

Regional Training & Development Manager

100 offices + 14-person team

2013 to 2016

Stockworth

Sales & Marketing Training Manager

74% YoY sales growth

Ask about Josh's experience

What are you curious to know about Josh?

Ask how Josh thinks, what he has built, how he leads, or what results he has produced. The portfolio contains direct evidence, and each response pairs his point of view with a relevant career example.

Career highlights and results

Six roles with increasing scope, from sales training to enterprise AI enablement.

Select any role to see the business need, what Josh built or led, and the result it produced.

RoleWhat Josh deliveredResult

Case 01 / 06AI enablement

PayPal · Enterprise AI Enablement Leader

Built an enterprise AI enablement system that connected fluency, tools, adoption, and measurable workflow gains.

Mar 2026 to present

The challenge

Move AI adoption beyond awareness and isolated prompting by anchoring the work to real roles, repeatable workflows, quality standards, and responsible use.

The approach

Mapped four AI tools to five jobs-to-be-done, built three enterprise tools end-to-end, and connected pilots to fluency, practice, champions, and measurement.

What changed

Measured use averaged 70% time savings, reached a 93% quality-outcome rate, and accelerated existing work in 80% of sessions.

Josh's contribution

Created the strategy and roadmap; led hands-on tool and workflow development; shaped role-based learning, pilot design, measurement, and cross-functional adoption work.

AI enablementWorkflow designLLM APIsChange leadershipMeasurement

Metrics reflect resume-backed outcomes, measured pilots, H1 reporting, or results delivered through Josh's leadership and contribution.

AI Builder

I build AI tools and workflows, not just the training around them.

Josh can define the business need, prototype the tool, build the workflow, and design the learning, safeguards, and measures around it.

Featured AI productMgmt On-Demand

The world's first AI-powered leadership coach, built with the OpenAI API.

Josh designed the product around the moments managers actually need help. The coach turned leadership frameworks into on-demand, situational guidance and extended development beyond scheduled programs.

OpenAI APICore technology

160+Leadership modules

3Delivery platforms

02 · Enterprise AI3 tools built end to end

Role-based PayPal tools connected to real jobs, human review, responsible-use standards, and adoption measures.

03 · Claude ecosystemDozens of reusable builds

Claude Skills, plugins, and Artifacts that turn repeat work into structured, repeatable capability.

04 · ChatGPT ecosystemAgents + Sites

Custom agents, interactive Sites, and recruiter-facing experiences designed around a clear job to be done.

05 · Technical fluencyAPIs + workflows

Hands-on prototyping across prompts, interfaces, plugins, automations, quality checks, and human decision points.

Skills and tools

Director-level strategy with hands-on AI and learning-system expertise.

Relevant experience for Director of Learning, AI Enablement, learning innovation, and enterprise transformation roles.

AI enablement

Build company-wide AI fluency around role-specific use cases, responsible practice, and measurable adoption.

AI fluency frameworksRole-specific use casesAgentic AI workshopsWorkflow redesignAI governanceChampion networksAdoption analytics

Applied AI building

Turn a defined business need into a working tool, agent, workflow, or proof of concept that people can test.

ChatGPTClaudeClaude SkillsClaude pluginsClaude ArtifactsChatGPT agentsChatGPT SitesLLM APIsIntelligent workflow design

Learning leadership

Lead learning portfolios, teams, platforms, and quality standards that stay connected to business performance.

Portfolio strategyInstructional designAdult learningLeadership developmentSimulation and scenario designLMS and knowledge basesQuality governanceLearning analyticsVideo production

Enterprise execution

Translate strategy into roadmaps, programs, stakeholder decisions, and measurable enterprise change.

Executive communicationCross-functional influenceRoadmap managementProgram managementResource planningOperating modelsGlobal change managementMeasurement strategy

Hands-on AI toolkitChatGPTClaudeCustom agentsLLM APIsReusable skillsPlugin workflows

How Josh approaches the work

Teach the system, not just the tool.

“The goal is not to make people use a tool. The goal is to make better work easier to do.”

Diagnose

Find the friction in the real workflow. Name the user, job, constraint, and quality bar.

Design

Shape the capability, learning journey, and human review around the needed behavior.

Ship

Build the smallest useful tool, pilot, or operating mechanism people can actually use.

Scale

Coach adoption, measure impact, clarify ownership, and institutionalize what proves valuable.

Ready to talk?

Need a leader who can connect learning, AI, and measurable execution?

Let's talk about the capability your organization needs next.

Email Josh ↗Connect on LinkedIn ↗