AI Enablement Facilitator / Trainer — Microsoft Copilot & Claude

Location: Chicago, IL — onsite 5 days/week, downtownType: Contract — $65–$70/hr W2Duration: Mid-November 2026 start through early March 2027, extension possibleSchedule: Monday–Friday, 9:00 AM–5:00 PM CentralAbout the RoleOur client, a global consumer goods company, is rolling out enterprise AI tools — Microsoft Copilot and Claude — across its workforce, and needs a hands-on trainer to help people actually use them.

You’ll sit on the company’s central learning team, facilitating sessions, running the logistics behind the rollout, and supporting a network of internal AI Champions.The title on the client’s side says Manager, but this is a delivery role, not a people-management one: most of your week is in front of learners — virtual, in person and hybrid — or building the guides, job aids and toolkits they use afterward.If you’ve trained people on new technology and you’re already using generative AI tools in your own work, this is that role.Key ResponsibilitiesFacilitate virtual, in-person and hybrid learning sessions on Microsoft Copilot, Claude, responsible AI practices and role-specific use casesRun live demos and gather learner feedbackCoordinate program deployment: scheduling, registration, participant communications, virtual connectivity and tracker maintenanceSupport onboarding, development and engagement of the AI Champions network, equipping them to promote responsible AI adoptionHelp design and update facilitator guides, participant materials, job aids, presentations and manager toolkits as AI features and policies changeRequired QualificationsBachelor’s degree2+ years in a technical training roleExperience facilitating learning sessions or workshops, supporting learning deployments, and creating learning materials and job aidsWorking knowledge of generative AI and enterprise AI tools such as Microsoft Copilot and ClaudeProficient in Microsoft Office, with advanced Excel skillsStrong public speaking, communication and stakeholder-management skills; organized and self-directedCuriosity and learning agility around emerging AI technologyMust live within daily commuting distance of downtown Chicago — onsite role, no relocation or per diemThis role requires the ability to work in the United States without sponsorship, now or in the future.Must be able to pass a background check and drug screenInterview ProcessOne panel video interview.Benefits (employee contribution)Health insuranceHealth savings accountDental insuranceVision insuranceFlexible spending accountsLife insuranceRetirement planAll qualified applicants will receive consideration for employment without regard to age, race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran. Rate of pay within the stated range will depend on the qualifications of the applicant.