Head of Flight

United States·AustinFull-timeexecutive

OtherHead

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Quick Summary

Overview

Skyways designs, builds, and operates fully autonomous long-range cargo aircraft. Founded in 2017,

Technical Tools

OtherHead

Skyways designs, builds, and operates fully autonomous long-range cargo aircraft. Founded in 2017, the company has spent the last eight years developing and deploying autonomous logistics systems for real-world operations.

Our V2 aircraft carries 30 lbs up to 500 miles, while our next-generation V3 carries 100 lbs over 1,000+ miles with 20+ hours of endurance. Both use a hybrid-electric architecture that takes off like a helicopter and cruises like a plane, enabling long-range autonomous delivery without traditional runway infrastructure.

Today, Skyways aircraft operate across three continents in controlled national airspace under FAA oversight and in support of U.S. military operations. We are transitioning from prototype development to full-rate production and scaling toward large autonomous cargo fleets.

Backed by Y Combinator and a $37M AFWERX STRATFI award from the U.S. Air Force, Skyways is building the future of autonomous logistics aviation from Austin, Texas.

The Opportunity

Skyways is looking for a Head of Flight to lead all flight testing and flight operations across our autonomous aircraft programs. This role owns the execution, safety, and scalability of flight activities spanning prototype development, operational deployments, customer demonstrations, and production fleet operations.

You will build and lead the organization responsible for safely operating autonomous aircraft in real-world environments while partnering closely with engineering to accelerate aircraft development and reliability. This is a highly cross-functional leadership role at the center of aircraft development, operations, and commercialization.

Own all flight testing and flight operations activities across Skyways aircraft programs

Build and lead the flight organization responsible for safe, scalable, and high-tempo autonomous aircraft operations

Develop and execute flight test campaigns for prototype, developmental, and production aircraft

Lead operational planning, airspace coordination, mission execution, and flight readiness processes

Establish flight test methodologies, operational procedures, safety systems, and risk management processes

Define operational standards, checklists, SOPs, and readiness review frameworks

Partner closely with autonomy, GNC, mechanical, electrical, manufacturing, and regulatory teams to validate aircraft performance and accelerate development

Drive operational feedback into aircraft design, reliability, maintainability, and mission capability improvements

Own flight safety culture, operational discipline, and incident response processes across the company

Support FAA engagement, certification efforts, military demonstrations, and customer operations

Recruit, mentor, and grow a high-performing team of flight operators, pilots, and flight test engineers

Help scale Skyways from prototype flight operations into repeatable commercial and defense deployment

8+ years of experience in flight test, flight operations, aviation operations, or UAS operations leadership

Experience leading complex flight campaigns for autonomous, unmanned, experimental, or highly integrated aircraft systems

Strong understanding of aviation safety, operational risk management, and flight readiness processes

Experience building operational procedures, test plans, and scalable flight operations frameworks

Demonstrated ability to lead multidisciplinary teams in fast-paced technical organizations

Excellent communication and decision-making skills in operational environments

Ability to balance safety, execution speed, and engineering development priorities

Strong familiarity with FAA operations, airspace coordination, and aviation regulations

Comfortable working hands-on in field environments, flight test operations, and deployment activities

Ability to travel as needed to support testing, demonstrations, and operational deployments

Led flight operations or flight test organizations for autonomous aircraft or advanced aviation programs

Worked on hybrid-electric, VTOL, or long-endurance aircraft systems

Held FAA pilot certifications, test pilot qualifications, or operational leadership positions

Supported military aviation programs or operational deployments

Built operational organizations from early-stage prototype programs through scaled deployment

Experience with BVLOS operations, Part 107 waivers, or experimental flight testing

Background in systems engineering, autonomy, or flight controls

Experience operating aircraft internationally or in austere environments

Due to U.S. government contract requirements, this role is limited to U.S. citizens, U.S. permanent residents, or candidates from specific countries authorized under applicable export control regulations.

Skyways is an Equal Opportunity employer committed to diversity in the workplace. All qualified applicants will receive consideration for employment without regard to race, color, religion, age, national origin, sex, sexual orientation, gender identity, disability, protected veteran status or any other factor protected by applicable local, state or federal laws.