Leadership Development Facilitator

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

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.