Senior Drone Pilot and Trainer, UAS

WingXpand, Inc.; Chicago (IL); Hybrid; USD 120,000 - 170,000; Full time

Benefits offered by this job

Stock options

Medical, dental, and vision coverage

401(k) retirement plan

Unlimited paid time off

Job summary

WingXpand, Inc. seeks a Senior UAS Pilot and Trainer to own how our robots are operated and how operators are trained. You will lead operations across aircraft, ground vehicles, and surface vessels, delivering demonstrations and on-site training for diverse customers.

You will build and oversee training content, ensure regulatory compliance, and travel ~30% to customer sites, military installations, and events. Equity and comprehensive benefits are offered.

Qualifications

• 5+ years operating unmanned aircraft in military, government, or defense.
• Experience as an instructor, standardization operator, evaluator, or master trainer.
• Hands-on experience with Group 1 or Group 2 UAS, fixed-wing preferred.

Responsibilities

• Serve as pilot in command for WingXpand aircraft during demonstrations, flight tests, training and customer events.
• Operate and instruct on unmanned ground vehicles and unmanned surface vessels.
• Own the operations program across all three domains — standardization, currency requirements, crew qualification standards, and the operations manual.
• Build and deliver the operator training program across classroom, simulator, and hands-on flight instruction, and certify operators.
• Write and maintain training documentation, standard operating procedures, checklists, and instructional materials.
• Train military, government, and commercial operators on platforms, payloads, and mission planning.

Skills

UAS operation

Instructor/trainer

Ground/Surface robotics

Flight safety

Regulatory compliance

Tools

UAS platforms Group 1/2

Flight simulators

ATAK

Job description

WingXpand 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 WingXpand scales, we are seeking high performers to grow with our team.

Job Description

We're hiring a Senior UAS Pilot and Trainer — the person who owns how our robots get operated, how everyone else learns to operate them, and how we show up in front of customers. You'll be the senior operator in the company across all three domains. Most of your time is on the aircraft, but our ground vehicle and surface vessel run the same core, and you'll be operating and teaching those too.

Key Responsibilities

• Serve as pilot in command for WingXpand aircraft during demonstrations, flight test, training, and customer events.
• Operate and instruct on our unmanned ground vehicle and unmanned surface vessel alongside the aircraft.
• Own the operations program across all three domains — standardization, currency requirements, crew qualification standards, and the operations manual.
• Build and deliver the operator training program across classroom, simulator, and hands‑on flight instruction, and certify operators against it.
• Write and maintain training documentation, standard operating procedures, checklists, and instructional materials.
• Train military, government, and commercial operators on our platforms, payloads, and mission planning.
• Manage airspace authorizations and regulatory compliance for company flight operations, including COAs, Part 107 waivers, restricted airspace requirements, and range coordination.
• Run internal flight test sorties for product validation and new capability evaluation, and capture structured data from them.
• Own flight safety — risk management, mishap investigation, and lessons learned.
• Represent WingXpand at customer demonstrations, exercises, and operational experimentation venues, from capability briefs to running the systems on a range.
• Support customer evaluations, exercises, operational testing, and field experimentation.
• Own customer relationships coming out of demonstrations and fieldings, and keep them warm between events.
• Support writing and establishing CONOPS.
• Help shape how we brief the capability — translating what operators need into how we describe and position the product.
• Assist customers with mission planning, system setup, troubleshooting, and operational best practices.
• Own the field feedback loop into engineering, turning what operators actually do into product and training changes.
• Travel to customer sites, military installations, and training events. Expect roughly 30%.

Qualifications

• 5+ years operating unmanned aircraft in a military, government, or defense industry role.
• Experience as an instructor, standardization operator, evaluator, or master trainer, formal or informal.
• Hands‑on experience with Group 1 or Group 2 UAS, fixed‑wing preferred.
• Interest in operating ground and surface robots as well as aircraft.
• Demonstrated ability to build training content, not only to deliver someone else’s.
• Genuine curiosity about how the system works, and interest in sitting with engineers to make it better rather than just reporting that it’s broken.
• A bias toward the end user. You should care whether an operator can actually run this thing under load, tired, in bad conditions.
• Excellent communication and presentation skills, and the credibility to hold a room of experienced operators.
• Calm and effective in the field — able to work independently, diagnose problems on the flight line, and keep a demonstration on track when something breaks.
• FAA Part 107 Remote Pilot Certificate, or the ability to obtain one within 30 days of hire.
• Willingness to travel regularly throughout the United States.

Additional Qualifications

• Prior military service in UAS operations, aviation, intelligence, reconnaissance, artillery, or special operations. Army 15W and 15E, the new 15X Tactical UAS Specialist, and 150U UAS Operations Technician all translate directly, as do USMC 7314 and equivalent Navy and Air Force ratings.
• Group 3 UAS or manned aviation experience. FAA Part 61 certificates, CFI, or ATP.
• Experience obtaining COAs, Part 107 waivers, or airworthiness releases.
• Experience supporting military exercises, operational testing, or field experimentation.
• Proposal or capture experience — SBIR, RFP responses, color team reviews, or past-performance writing.
• An existing network in the Army, SOF, or public safety UAS community.
• Experience in a field service representative, field applications, or customer‑facing defense industry role.
• Familiarity with ATAK, tactical radios, mission planning software, and autopilot ground control stations.
• Experience building a training program or syllabus from scratch.

Every full-time employee at WingXpand receives stock options. Equity is a core part of how we pay, not an afterthought, and early team members share directly in the company's growth as we scale. Additionally, we offer medical, dental, and vision coverage, a 401(k) retirement savings plan, and unlimited paid time off for vacation, illness, and personal needs, plus paid company holidays.

What Else You Need to Know

This role requires access to technology controlled under U.S. export regulations. Applicants must qualify as a U.S. Person as defined at 22 CFR 120.62, which includes U.S. citizens, U.S. nationals, lawful permanent residents, and persons granted asylum or refugee status.

WingXpand is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, protected veteran status, or any other characteristic protected by federal, state, or local law.

Qualified individuals with disabilities and protected veterans are encouraged to apply. If you need a reasonable accommodation to complete any part of the application or interview process, contact [e-mail] and we'll arrange it.