Lead Trainer — Enterprise AI

JLL • Chicago, IL

5d • Remote

About The Position

JLL empowers you to shape a brighter way. Our people at JLL are shaping the future of real estate for a better world by combining world class services, advisory and technology for our clients. We are committed to hiring the best, most talented people and empowering them to thrive, grow meaningful careers and to find a place where they belong. Whether you’ve got deep experience in commercial real estate, skilled trades or technology, or you’re looking to apply your relevant experience to a new industry, join our team as we help shape a brighter way forward. About the Role JLL seeks a Lead Trainer to join the Enterprise AI team to design, deliver, and scale training programs driving AI adoption across our 100,000+ employee AI portfolio. This senior individual contributor owns the breadth of the enterprise AI training portfolio — from foundational onboarding to persona-based enablement to agent platform training. A core part of this role is building and managing the Citizen Trainers network, ensuring JLL's training reach scales far beyond the central team. You'll work independently with L&D and cross-functional business line stakeholders, exercise significant judgment in program design, and build scalable infrastructure that multiplies impact beyond central capacity. What You'll Do Training Portfolio Design & Delivery • Own the end-to-end enterprise AI training portfolio — from Intro to AI@JLL onboarding through persona-based webinars, monthly webinar series, and AI mastery courses • Design and deliver domain-specific curricula for major business lines connecting AI capabilities to business outcomes • Build and maintain multi-format content: live workshops, self-paced e-learning modules, videos, quick reference guides, and interactive simulations • Deliver high-impact training sessions (virtual and in-person) with measurable learning outcomes • Manage the training calendar and coordinate scheduling, platform logistics, attendee management, and post-session follow-up Citizen Trainer Enablement & Coordination • Build, enable, and manage the Citizen Trainers community — recruiting, onboarding, certifying, and supporting a cross-functional group of 25+ trainers delivering 10+ sessions/month • Develop train-the-trainer frameworks, toolkits, playbooks, and ongoing support systems that ensure quality and consistency at scale • Monitor Citizen Trainer output and effectiveness — tracking sessions delivered, attendee activation rates, and feedback scores • Serve as the primary point of contact for Citizen Trainers, providing coaching, content updates, and escalation support Scalable Infrastructure & Measurement • Create a self-service learning ecosystem with 50+ assets and systematic refresh cycles aligned to product releases • Implement learning effectiveness measurements tracking training completion, user proficiency, feature utilization post-training, and the 1.3x training effectiveness multiplier • Analyze training data to optimize programs, identify gaps, and demonstrate business impact and ROI • Partner with the enterprise L&D team to leverage the LMS and embed AI training into existing organizational learning pathways Product & GTM Integration • Align training roadmap with product releases ensuring users are ready for new features and capabilities at launch • Support agent platform rollout with training strategies, onboarding motions, and enablement materials • Surface training insights that inform the Product roadmap and UX improvements • Coordinate with GTM and communications teams to ensure training promotions reach the right audiences through the right channels What You Bring Experience • 7+ years training design/delivery in enterprise technology or digital transformation • 3+ years building and managing train-the-trainer or distributed enablement programs at scale • Demonstrated success building scalable training models serving 1,000+ employees • Proven track record measuring and reporting training ROI Technical Skills • Proficient with generative AI tools (e.g., JLL GPT, ChatGPT, Claude, Copilot) and enterprise AI applications • Experience with LMS platforms, authoring tools (e.g., Articulate, Synthesia, Camtasia), and learning analytics • Strong data literacy analyzing training metrics and demonstrating business impact Competencies • Works independently on complex initiatives across business lines with minimal supervision • Exercises significant judgment determining priorities, methods, and approaches • Leads non-reporting staff and ensures stakeholder buy-in and cooperation • Influences senior stakeholders through credibility and expertise • Strong operational instincts — able to manage a portfolio of concurrent programs, trainers, and content while maintaining quality

Requirements

• 7+ years training design/delivery in enterprise technology or digital transformation
• 3+ years building and managing train-the-trainer or distributed enablement programs at scale
• Demonstrated success building scalable training models serving 1,000+ employees
• Proven track record measuring and reporting training ROI
• Proficient with generative AI tools (e.g., JLL GPT, ChatGPT, Claude, Copilot) and enterprise AI applications
• Experience with LMS platforms, authoring tools (e.g., Articulate, Synthesia, Camtasia), and learning analytics
• Strong data literacy analyzing training metrics and demonstrating business impact
• Works independently on complex initiatives across business lines with minimal supervision
• Exercises significant judgment determining priorities, methods, and approaches
• Leads non-reporting staff and ensures stakeholder buy-in and cooperation
• Influences senior stakeholders through credibility and expertise
• Strong operational instincts — able to manage a portfolio of concurrent programs, trainers, and content while maintaining quality

Nice To Haves

• Certification in instructional design, adult learning, or change management (ATD, CPTD, Prosci)
• Professional services or management consulting experience
• Real estate industry knowledge

Responsibilities

• Own the end-to-end enterprise AI training portfolio — from Intro to AI@JLL onboarding through persona-based webinars, monthly webinar series, and AI mastery courses
• Design and deliver domain-specific curricula for major business lines connecting AI capabilities to business outcomes
• Build and maintain multi-format content: live workshops, self-paced e-learning modules, videos, quick reference guides, and interactive simulations
• Deliver high-impact training sessions (virtual and in-person) with measurable learning outcomes
• Manage the training calendar and coordinate scheduling, platform logistics, attendee management, and post-session follow-up
• Build, enable, and manage the Citizen Trainers community — recruiting, onboarding, certifying, and supporting a cross-functional group of 25+ trainers delivering 10+ sessions/month
• Develop train-the-trainer frameworks, toolkits, playbooks, and ongoing support systems that ensure quality and consistency at scale
• Monitor Citizen Trainer output and effectiveness — tracking sessions delivered, attendee activation rates, and feedback scores
• Serve as the primary point of contact for Citizen Trainers, providing coaching, content updates, and escalation support
• Create a self-service learning ecosystem with 50+ assets and systematic refresh cycles aligned to product releases
• Implement learning effectiveness measurements tracking training completion, user proficiency, feature utilization post-training, and the 1.3x training effectiveness multiplier
• Analyze training data to optimize programs, identify gaps, and demonstrate business impact and ROI
• Partner with the enterprise L&D team to leverage the LMS and embed AI training into existing organizational learning pathways
• Align training roadmap with product releases ensuring users are ready for new features and capabilities at launch
• Support agent platform rollout with training strategies, onboarding motions, and enablement materials
• Surface training insights that inform the Product roadmap and UX improvements
• Coordinate with GTM and communications teams to ensure training promotions reach the right audiences through the right channels

Benefits

• Personalized benefits that support personal well-being and growth: JLL recognizes the impact that the workplace can have on your wellness, so we offer a supportive culture and comprehensive benefits package that prioritizes mental, physical and emotional health. Some of these benefits may include:
• 401(k) plan with matching company contributions
• Comprehensive Medical, Dental & Vision Care
• Paid parental leave at 100% of salary
• Paid Time Off and Company Holidays
• Early access to earned wages through Daily Pay

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed