UAS​/Drone Pilot & Training Specialist | Defense

Locations

Chicago (Schaumburg), IL

Full-time, Part-time, or Contract | Open 6/29/26 | Close 7/13/26

Wing Xpand is Expanding What’s Possible™ with Autonomous Systems, building long-endurance, backpackable smart plane drones and robotics systems that support defense, public safety, disaster response, and commercial missions. Our platforms operate across air, ground, and maritime domains, integrating autonomy, AI-powered sensing, edge computing, and networked systems to deliver real-world intelligence and threat detection. We design, build, and deploy complete systems — hardware, software, and data — and we move fast.

As Wing Xpand scales, we are seeking high performers to grow with our team.

Wing Xpand is seeking experienced pilots and trainers to help deliver the next generation of autonomous systems to the U.S. military and defense community. This is a hands on role for professionals who thrive in the field, enjoy teaching others, and want to help shape how autonomous aircraft are deployed across real world missions. You will conduct flight operations, support military demonstrations, train operators, develop training materials, and work directly with customers to ensure mission success.

You will serve as the face of Wing Xpand during customer engagements, helping operators build confidence while providing valuable feedback that improves our products. This role is for leaders who remain calm under pressure, communicate clearly, solve problems in the field, and take ownership of every mission. If you are passionate about supporting those who serve, enjoy working with cutting edge technology, and want to help define the future of autonomous systems, we want to hear from you.

• Conduct flight operations for Wing Xpand autonomous aircraft during demonstrations, testing, training, and customer events
• Train military, government, and commercial operators on Wing Xpand systems and mission planning
• Develop and deliver classroom, simulator, and hands on flight training
• Support customer evaluations, exercises, and operational field events
• Represent Wing Xpand during military demonstrations, conferences, and customer engagements
• Assist customers with mission planning, system setup, troubleshooting, and operational best practices
• Capture customer feedback and work closely with engineering to improve products and training
• Develop training documentation, standard operating procedures, and instructional materials
• Support internal flight testing, product validation, and new capability evaluations
• Travel regularly to customer sites, military installations, and training events

• Military service or government aviation experience preferred
• 2 to 10+ years of experience operating unmanned aircraft, aviation systems, or military equipment
• Experience instructing, coaching, or training operators in technical systems
• Excellent communication and presentation skills
• Comfortable working independently in dynamic field environments
• Strong problem solving skills with the ability to adapt quickly during customer operations
• Willingness to travel extensively throughout the United States

• Prior military service in aviation, intelligence, reconnaissance, special operations, artillery, or unmanned aircraft operations
• Experience operating Group 1, Group 2, or Group 3 UAS platforms
• FAA Part 107 Remote Pilot Certificate
• Military Instructor, Master Trainer, Standardization, or Evaluator qualifications
• Experience supporting military exercises, operational testing, or field experimentation
• Active U.S. Security Clearance or ability to obtain one
• Experience with mission planning software, radios, tactical communications, or ATAK

To conform to U.S. Government aerospace technology export regulations, applicant must be a 'U.S. Person' (U.S. Citizen or a Permanent Resident/Green Card Holder).

If you are a self-motivated, results-driven individual with a passion for innovation and technology, we want to hear from you!