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Leadership Enablement Associate
Job in
Chicago, Cook County, Illinois, 60290, USA
Listed on 2026-08-02
Listing for:
Jobtailor
Full Time
position Listed on 2026-08-02
Job specializations:
-
Education / Teaching
Professional Development
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
- 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)
Position Requirements
10+ Years
work experience
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