Digital Operations Enablement Trainer

JLL•Chicago, CO

18h•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. JLL - WPM Digital Operations Enablement Trainer Work Schedule: Remote, M-F 9-5 Travel Requirements: up to 50% to support in-person training & engagements Reports to: Sr. Director, Digital Transformation Operational Solutioning Estimated compensation for this position is: $110K - $130K + 20% annual bonus What this job involves: The Digital Operations Enablement Trainer is responsible for developing and delivering training content that drives adoption of the digital tools and products used across JLL's Workplace Management (WPM) operations. This role serves as the primary training resource for WPM's digital ecosystem — spanning Corrigo, WPOS (Workplace OS) AI-enabled agent tiles, Power BI, SharePoint, Teams, and other platforms that support facilities management and operations delivery. Working closely with the Operations Enablement & Solutions Lead and technology partners, this individual translates complex platform functionality into clear, practical training content for account teams, technicians, and administrative staff. The role also applies AI tools to streamline training content creation and maintenance, ensuring materials stay current as platforms evolve. The ideal candidate combines strong instructional design and delivery skills with hands-on WPM operational knowledge and comfort using AI to accelerate content development. What your day-to-day will look like: Training Needs Analysis & Strategy Conduct training needs analyses across WPM digital tools and platforms to identify skill gaps, adoption barriers, and content priorities. Develop training roadmaps aligned to platform releases, pilot deployments, and full-scale rollouts. Partner with the Operations Enablement & Solutions Lead to prioritize training investments based on business impact. Training Content Development Design and develop training materials — including e-learning modules, job aids, quick-reference guides, facilitator guides, and video walkthroughs — for Corrigo, WPOS, and other WPM digital tools. Translate technical platform documentation and requirements into learner-friendly content tailored to field, account, and administrative audiences. Maintain a centralized, version-controlled library of training assets that stays current with platform updates and enhancements. Training Delivery & Facilitation Deliver engaging live and virtual training sessions using a variety of instructional techniques suited to diverse learner populations. Facilitate train-the-trainer sessions to build sustainable, scalable training capability across account teams. Support onboarding of new users during platform migrations, pilot deployments, and system go-lives. Digital Tools & Platform Enablement Serve as the training subject matter expert across the WPM digital toolset, including Corrigo, WPOS AI agent tiles (e.g., Invoice Reminder, Invoice Approval), Power BI, SharePoint, and Teams. Partner with platform owners and technology teams to stay current on new features, configuration changes, and upcoming releases. Support Business Readiness Testing (BRV) and UAT activities by capturing training-relevant findings and translating them into content updates. AI-Enabled Training Efficiency Apply AI tools to accelerate the development, updating, and localization of training content, reducing time-to-deployment for new materials. Identify opportunities to use AI-powered authoring, summarization, and content-generation tools to scale training output without sacrificing quality. Stay current on emerging AI capabilities relevant to learning and development, and recommend tools that improve training efficiency and effectiveness. Training Effectiveness & Continuous Improvement Evaluate training effectiveness through assessments, learner feedback, and adoption metrics; use findings to refine content and delivery methods. Analyze training and support data to identify recurring knowledge gaps and proactively address them with updated content. Continuously benchmark training practices against industry trends in adult learning and digital enablement. Cross-Functional Collaboration & Stakeholder Engagement Collaborate with subject matter experts, account operations leads, and technology partners to ensure training accuracy and relevance. Partner with the Operations Enablement & Solutions Lead on change management initiatives, ensuring training is integrated into broader technology deployment and adoption plans. Represent training priorities and learner feedback in cross-functional planning discussions.

Requirements

Bachelor's degree in Instructional Design, Education, Human Resources, Business, or a related field (or equivalent experience)
Minimum 5 years of experience in training, instructional design, or learning & development, ideally within a technology, facilities management, or operations environment.
Demonstrated experience developing and delivering training for enterprise software platforms; direct experience with Corrigo, IWMS/CMMS, or comparable systems strongly preferred.
Experience using AI-powered tools to develop, update, or scale training content.
Proven ability to manage multiple training projects simultaneously in a fast-paced environment.
Proficiency with learning management systems (LMS), e-learning authoring tools, and digital content platforms.
Working knowledge of AI tools for content generation, summarization, and training efficiency.
Strong understanding of adult learning principles and instructional design methodologies.
Ability to produce high-quality training deliverables: e-learning modules, job aids, facilitator guides, and assessments.
Comfort working across digital collaboration platforms (e.g., SharePoint, Teams, Power BI) to source content and distribute materials.

Nice To Haves

Operational knowledge of WPM (Workplace Management) service delivery, account structure, or facilities management processes.
Familiarity with the Corrigo work order management platform and/or JLL's WPOS (Workplace OS) tools.
Experience supporting technology pilot deployments, UAT, or Business Readiness Testing (BRV).
Certification in instructional design (e.g., CPTD, ATD) or e-learning development.
Willingness to travel as needed to support in-person training and account engagements.

Responsibilities

Conduct training needs analyses across WPM digital tools and platforms to identify skill gaps, adoption barriers, and content priorities.
Develop training roadmaps aligned to platform releases, pilot deployments, and full-scale rollouts.
Partner with the Operations Enablement & Solutions Lead to prioritize training investments based on business impact.
Design and develop training materials — including e-learning modules, job aids, quick-reference guides, facilitator guides, and video walkthroughs — for Corrigo, WPOS, and other WPM digital tools.
Translate technical platform documentation and requirements into learner-friendly content tailored to field, account, and administrative audiences.
Maintain a centralized, version-controlled library of training assets that stays current with platform updates and enhancements.
Deliver engaging live and virtual training sessions using a variety of instructional techniques suited to diverse learner populations.
Facilitate train-the-trainer sessions to build sustainable, scalable training capability across account teams.
Support onboarding of new users during platform migrations, pilot deployments, and system go-lives.
Serve as the training subject matter expert across the WPM digital toolset, including Corrigo, WPOS AI agent tiles (e.g., Invoice Reminder, Invoice Approval), Power BI, SharePoint, and Teams.
Partner with platform owners and technology teams to stay current on new features, configuration changes, and upcoming releases.
Support Business Readiness Testing (BRV) and UAT activities by capturing training-relevant findings and translating them into content updates.
Apply AI tools to accelerate the development, updating, and localization of training content, reducing time-to-deployment for new materials.
Identify opportunities to use AI-powered authoring, summarization, and content-generation tools to scale training output without sacrificing quality.
Stay current on emerging AI capabilities relevant to learning and development, and recommend tools that improve training efficiency and effectiveness.
Evaluate training effectiveness through assessments, learner feedback, and adoption metrics; use findings to refine content and delivery methods.
Analyze training and support data to identify recurring knowledge gaps and proactively address them with updated content.
Continuously benchmark training practices against industry trends in adult learning and digital enablement.
Collaborate with subject matter experts, account operations leads, and technology partners to ensure training accuracy and relevance.
Partner with the Operations Enablement & Solutions Lead on change management initiatives, ensuring training is integrated into broader technology deployment and adoption plans.
Represent training priorities and learner feedback in cross-functional planning discussions.