Lead UAS Pilot and Trainer

WingXpand; Illinois; On-site; USD 110,000 - 170,000; Full time

Benefits offered by this job

Stock options

Medical coverage

Dental coverage

Vision coverage

401(k) retirement plan

Unlimited PTO

Job summary

WingXpand in Schaumburg, IL seeks a Lead UAS Pilot and Trainer to own how our drones are operated and how the team learns to operate them. You will be the senior operator across air, ground vehicle, and surface vessel domains, conducting demonstrations at military installations and leading training.

The role combines hands-on flight work with customer-facing responsibilities, including briefings, proposals, and field exercises.

Qualifications

• 5+ years operating unmanned aircraft in a defense/government role.
• Experience as an instructor or trainer and in standardization.
• Proven ability to develop and deliver training programs.
• Customer-facing experience at events, demonstrations, and briefs.
• Willingness to travel up to ~40% and work in field environments.

Responsibilities

• Pilot in command during demonstrations, flight test, training, and customer events.
• Instruct on unmanned ground vehicle and unmanned surface vessel alongside the aircraft.
• Own the operations program across standardization, currency requirements, crew qualification standards, and the operations manual.
• Build and deliver operator training across classroom, simulator, and hands-on flight instruction.
• Write and maintain training documentation, SOPs, and instructional materials.
• Train military, government, and commercial operators on platforms and payloads.
• Manage airspace authorizations and regulatory compliance for company flight operations.
• Run internal flight test sorties for product validation and capture structured data.
• Own flight safety, risk management, and lessons learned.

Skills

Flight operations

Instructor experience

Customer engagement

Regulatory compliance

Education

FAA Part 107 Remote Pilot Certificate

Tools

Group 1/2 UAS

Job description

Type & Location: Full-Time | Part-Time | Contractor| Chicago (Schaumburg), IL

Open: 9/17/26

Close: 10/1/26

AboutWingXpand

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 our Lead 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. That means being in the field: flying and driving demonstrations at military installations, standing up training for Army, SOF, and public safety operators, and running our own test sorties. It also means owning the program behind the flying - standardization, currency, the training syllabus, the operations manual, and the qualification standards every operator we field is held to.

When a customer asks who certifies that our crews are ready, that's you. The other half of this job is customer-facing, and we want to be straight about what that means. You'll be in front of program offices and units at industry events, capability demonstrations, exercises, and operational experimentation venues — some of those are a conference hall, some are a range in the middle of nowhere. You'll brief capability and help write the proposals that turn a good demonstration into a contract. If the word \"sales\" makes you wince, we understand — and the reason we want an operator in this seat rather than a salesperson is that the best person to explain these systems to a squad leader is someone who has run them in bad weather at four in the morning. You won't be pitching a product you don't understand. You'll be telling other operators the truth about systems you use yourself, including what they don't do yet.

This role is based at our Schaumburg facility, twenty minutes from O'Hare, which for a job with travel beats being near almost any installation. You'll also work in the same building as the engineers who design and build the aircraft. That's rare in this industry, where the operators are usually in one place and the product team is somewhere else, and it's the difference between filing feedback and walking it over to the person who can act on it. Add Midwest cost of living and the offer goes considerably further here than the same number does in San Diego, Dallas, or Northern Virginia. If you've spent a career moving every few years, this is somewhere you can buy a house and stay. The person who does well here is still curious. You'll sit next to the engineers who design and build these aircraft, and the ones who thrive in this role spend as much time asking why the autopilot did that as they do running the syllabus.

If you care more about whether an operator can actually use the thing at 0300 with cold hands than about whether the demo looked clean, and you want a hand in fixing what doesn't work rather than explaining it away, this is the right seat. If you've come out of a UAS operator, standardization, or instructor billet, you'll be at home here. This is a role with ownership rather than another seat on someone else's training contract — if you've spent years running a syllabus you didn't write and wanted to write your own, this is that job.

Key Responsibilities

Flight Operations and Training

• 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.

Customer Engagement and Business Development

• Represent WingXpand at industry events, 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 proposal development, including SBIR submissions, RFP and RFI responses, white papers, and past-performance and CONOPS sections.


• Help shape how we pitch 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, trade shows, and training events. Expect roughly 40%.

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. We don't expect you to arrive with UGV or USV time - we expect you to want it.


• Demonstrated ability to build training content, not only to deliver someone else's.


• Comfortable in a customer-facing role - briefing program offices, working an industry event, and representing a company rather than a unit.


• 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. We'll cover the cost.


• 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.