Training & Development Specialist - Frontline Leadership; Facilitator

Job Overview

Title: Training & Development Facilitator – Frontline Leadership
Location: Chicago, IL (Remote US Only, Hybrid/Remote 0-2 days onsite at Willis Tower per week as needed)
Travel: 60% travel nationwide to hub locations (Dallas, LA, Washington, Orlando, etc)
Duration & Type: Initial 6-month contract with potential extension or conversion
Compensation: Competitive hourly W2 rate ($38-39 per hour) with access to healthcare and dental insurance plans

Chamberlain Advisors is seeking a Training & Development Specialist – Frontline Leadership (Facilitator) for a client in the airline industry. This role is highly facilitation-focused and supports the launch of a new leadership training program for Technical Operations supervisors. The primary responsibility is delivering instructor-led, in-person leadership training across multiple U.S. hub locations. The role is ideal for an experienced facilitator who can confidently engage operational audiences, manage challenging group dynamics, and adapt delivery in fast-paced, real-time environments.

• Facilitate in-person, instructor-led leadership training for Tech Ops supervisors across multiple U.S. hub locations
• Deliver discussion-based sessions focused on leadership, communication, accountability, and people-management skills
• Encourage peer learning by drawing out real-world examples and guided discussion from participants
• Adapt facilitation style to varying audience engagement levels, operational context, and union dynamics
• Actively manage classroom dynamics, including highly vocal groups and disengaged participants
• Maintain alignment with learning objectives, session timing, and expected outcomes
• Participate in Train-the-Trainer onboarding prior to deployment
• Co-facilitate alongside an operational leader who supports technical or role-specific questions
• Support feedback collection and summarize learner insights to help measure training effectiveness
• Assist with scheduling coordination, session logistics, and stakeholder communication as needed
• Contribute to training impact measurement and continuous improvement efforts
• Provide support to additional leadership or soft-skills initiatives outside the initial deployment, as needed

• Demonstrated experience facilitating instructor-led training (ILT) for adult learners
• Experience delivering leadership, supervisory, or professional development training
• Experience working within operational, frontline, or union-based environments
• Strong classroom management, communication, and facilitation skills
• Ability to travel frequently and work in fast-paced, real-time settings
• Prior experience as a frontline leader or supervisor
• Background in aviation, transportation, logistics, manufacturing, utilities, or similarly regulated industries
• Experience facilitating leadership or soft-skills training (non-technical)
• Exposure to training logistics, scheduling, or light project coordination

• Hybrid role with limited on-site presence at Willis Tower (primarily for meetings)
• Approximately 60% travel during active deployment
• Weekly travel (typically ~2 days/week) for 8–10 weeks, rotating across U.S. hub locations
• Expected hubs may include:
  Chicago, Houston, San Francisco, Los Angeles, Washington DC, Orlando, and New York
• Candidates may be based anywhere in the U.S.;
  Central Time preferred

With over 90,000 employees across the world, our client is a leader in the airline industry, dedicated to delivering profitability, sustainable long-term value, and innovative employee development. The organization empowers employees to advance their professional careers through continuous skill development.

Chamberlain Advisors is a veteran-owned business that provides human capital solutions through contract, direct-hire, and retained-search opportunities. Our unique 5‑step recruitment process ensures a top‑line experience, helping you succeed in your job search.

Chamberlain Advisors provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race,…