Lead Trainer — Enterprise AI

JLL • Chicago, CO

5d • Remote

About The Position

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.

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

• 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
• Number of Employees: 5,001-10,000 employees