Leadership Enablement Associate

Jobtailor; Chicago (IL); On-site; USD 70,000 - 100,000; Full time

Job summary

Jobtailor in Chicago seeks an experienced leadership development facilitator to drive quarterly rock reviews across member companies, and annual planning sessions. You will partner with the Learning & Development team to design and deliver leadership workshops, create guides, and track outcomes.

You will also help translate leadership principles into practical tools, support onboarding for new leaders, and manage coaching engagements and program results.

Qualifications

• 3–6 years experience in leadership development or related fields.
• Strong group facilitation skills in professional settings.
• Ability to translate concepts into practical tools and discussions.
• Excellent organization and project management abilities.
• Experience supporting multiple business units (preferred).

Responsibilities

• Facilitate quarterly leadership reviews across member companies.
• Lead annual planning sessions and ensure alignment with SVP direction.
• Design and deliver leadership development workshops with L&D.
• Create facilitator guides, playbooks, and training materials.
• Track coaching engagements and program outcomes.
• Support onboarding and leadership development for new leaders.

Skills

Leadership development

Facilitation

Training materials

Project management

Emotional intelligence

Goal-oriented

EOS familiarity

Job description

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 discussionsExcellent 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)