About The Squadron

The Squadron USA is a premier center of excellence transforming traditional management training into high-impact, real-time experiences. Leveraging elite F-35 flight simulators and methodologies inspired by global air forces, we deliver immersive workshops that develop leadership, communication, and performance under pressure. Participants gain powerful tools and concrete insights through experiential learning, mission planning, and the pilot’s debriefing process—applying fighter pilot principles to today’s business challenges.

About This Opportunity

We are building a pool of Workshop Facilitators to lead corporate workshops at The Squadron NYC. Facilitators join as independent contractors and are engaged on demand basis.

This is ideal for active or former military aviators who are natural communicators and want to turn their flight-deck experience into real impact for business leaders – alongside their other work, not instead of it.

This is not a lecturer role. It is a high-impact performance role that requires presence, authority, credibility with the room, and the ability to read and adapt to a group in real time.

What You’ll Do

• Lead the pre-flight briefing: set the mission, the stakes, and the tone for the group.
• Guide teams through simulator-based missions, keeping energy and engagement high from start to finish.
• Facilitate structured debriefs that connect what happened in the simulator to real workplace behavior – communication, decision-making, planning, adaptability, and accountability.
• Manage group dynamics with confidence, from strong personalities to disengaged participants and executive audiences.
• Tailor your delivery to each group’s industry, seniority, and team maturity.
• Leave participants with clear takeaways they can apply the next day.
• Share feedback after sessions to help us keep improving our programs and methodology.

Qualifications

Required

• Military aviation background (pilot or aircrew) from any branch. Experience in high-stakes, team-based flight operations, and in mission briefing and debriefing, is a strong plus.
• Strong public speaking skills and a natural ability to engage, energize, and command an audience.
• Proven ability to run live sessions with groups, including senior or skeptical participants.
• Excellent interpersonal communication, emotional intelligence, and adaptability.
• Comfortable in fast-paced, high-energy, simulation-driven environments.
• Flexibility to be available on demand, including some evenings, on short notice.

An Advantage

• Any other corporate \ business experience – we look for variety of experiences that we can translate from the world of aviation to what corporate teams and leadership can take to their day-to-day routines, and create a culture of excellency in their organization.
• Background in organizational development, organizational psychology, leadership development, or learning & development – through experience, a degree (e.g., Master’s in Organizational Behavior/Development, Organizational Psychology, or Leadership), or both.
• Familiarity with leadership and team-effectiveness frameworks (e.g., experiential learning cycles, psychological safety, high-performing teams).
• Experience facilitating or presenting to executive and corporate audiences.
• Certification in coaching, facilitation, or a relevant leadership framework.
• Civilian aviation experience.

Terms

This is an independent contractor engagement. Facilitators are paid a per-session fee agreed in advance, work on their own schedule, and are not guaranteed a minimum number of sessions. The volume of work depends on client demand and your availability.