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Leadership Enablement Associate

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Jobtailor
Full Time position
Listed on 2026-08-02
Job specializations:
  • Education / Teaching
    Professional Development
Salary/Wage Range or Industry Benchmark: 70000 - 100000 USD Yearly USD 70000.00 100000.00 YEAR
Job Description & How to Apply Below

Responsibilities

  • Facilitate quarterly rock review sessions across Member Companies
  • Facilitate annual planning ("boulder setting") sessions
  • Support leadership teams in maintaining clarity on priorities and accountability
  • Ensure sessions stay structured, productive, and aligned with SVP direction
  • Maintain facilitation materials, templates, and session documentation
  • Partner with the Learning & Development team to design and deliver leadership development workshops
  • Support training programs for first-time managers, new Member Company Presidents, operational leadership teams
  • Help translate leadership principles into practical tools and exercises
  • Assist with development programs that build future leadership bench strength
  • Create facilitator guides, playbooks, and training materials
  • Support the creation of scalable leadership learning paths
  • Develop training modules for workshops, leadership sessions, and onboarding
  • Work closely with internal subject matter experts to capture and package best practices
  • Facilitate onboarding sessions for new Member Companies
  • Help leadership teams establish cadence, accountability structures, and operating rhythms
  • Ensure new MCs integrate smoothly into TCC’s leadership frameworks
  • Help manage TCC’s external executive coaching bench
  • Coordinate coach matching for leaders when development needs arise
  • Support SVPs in selecting appropriate coaches and defining engagement scope
  • Track coaching engagements and learning outcomes
  • Track participation, engagement, and feedback across leadership programs
  • Monitor consistency of operating cadence across MCs
  • Provide insights to leadership on program effectiveness and adoption
  • Continuously refine learning experiences based on feedback and outcomes
Requirements
  • 3–6 years experience in leadership development, consulting, operations, or organizational development
  • Strong facilitation skills in group settings
  • Experience creating professional training materials and presentations
  • Ability to translate leadership concepts into practical tools and discussions

    Excellent organization and project management skills
  • High emotional intelligence and ability to meet leaders where they are
  • Curiosity and humility — someone who listens before prescribing solutions
  • Familiarity with EOS or similar operating frameworks (Preferred)
  • Experience supporting multiple business units or portfolio companies (Preferred)
  • Experience facilitating leadership workshops (Preferred)
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Position Requirements
10+ Years work experience
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