Learning Manager (Chicago)

Manager, Learning & Capability BuildingCompany: Confidential Global Hospitality OrganizationLocation: Chicago, IL (Hybrid)Workplace Type: HybridPay Rate: $55–$60/hour (W2)Employment Type: ContractDuration: 6+ MonthsOverviewA global hospitality organization is seeking a Manager, Learning & Capability Building to support the execution and continuous improvement of a high-impact Brand Immersion training program aligned to sales enablement and business growth initiatives.This role will focus on equipping development and commercial teams with the knowledge, tools, and practical understanding needed to position and apply brand standards within real-world development and owner engagement scenarios. The ideal candidate is highly execution-oriented and thrives as a hands-on builder capable of translating strategic concepts into engaging, practical learning experiences.The position will partner closely with brand, development, growth, and learning stakeholders across a matrixed enterprise environment to drive learning adoption, business alignment, and measurable outcomes.Key ResponsibilitiesOwn end-to-end execution of the Brand Immersion training program, including rollout, enhancement, and continuous improvement initiativesBuild and deliver engaging learning experiences, including outlining content, structuring modules, and developing interactive learning componentsTranslate brand pillars, experience principles, and development standards into practical and commercially relevant learning contentCreate and refine instructional materials, including written content, learning copy, presentation materials, and interactive experiencesPartner with creative and design resources to develop visually effective learning solutionsEnsure training experiences are practical, engaging, and applicable to real-world business and development scenariosManage stakeholders, timelines, priorities, and deliverables across a fast-paced matrixed organizationMeasure training effectiveness, collect feedback, and continuously optimize learning experiencesLeverage AI-powered tools and modern content development technologies to improve speed, scalability, and quality of program executionRequired Qualifications5+ years of experience in Learning & Development, Sales Enablement, Program Management, or related fieldsProven experience executing programs end-to-end within enterprise environmentsStrong ability to translate strategic concepts into practical, user-friendly deliverablesComfortable operating as a hands-on contributor in a fast-paced and evolving environmentStrong stakeholder management, communication, and organizational skillsDemonstrated success driving adoption, engagement, and real-world application of learning programsBachelor's degree in Communications, Education, Business, or related field, or equivalent practical experiencePreferred QualificationsExperience supporting sales enablement or commercial training initiativesExperience designing blended learning solutions across multiple delivery methodsFamiliarity with LMS/LXP platforms and learning ecosystemsExperience leveraging data and analytics to measure learning effectiveness and improve outcomesExperience with modern learning and content creation tools such as Articulate, Synthesia, Canva, or similar platformsExperience leveraging AI tools to accelerate content development and program executionWhy This OpportunityOpportunity to contribute to a globally recognized hospitality organization's growth and learning initiativesHigh-visibility role partnering across brand, development, and commercial leadership teamsHands-on opportunity to build impactful learning experiences that directly support business outcomesCollaborative, fast-paced environment focused on innovation, capability building, and continuous improvementAbout PeopleCaddiePeopleCaddie connects organizations with high-impact consulting and professional talent through a hybrid recruiting model that combines advanced technology with experienced staffing professionals. Our approach is simple: technology when you want it, people when you don't.