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Skyways
Skyways

Head of Flight

Austin, Texas, U.S.
Full-Time

TLDR

This critical leadership role defines and scales all flight operations and testing for autonomous cargo aircraft, ensuring safety and regulatory compliance as the company prepares for global scale.

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 growing, and we're looking for a Head of Flight. This is a critical leadership role that will define, lead, and scale all flight operations and flight testing. You'll ensure safety, regulatory compliance, and operational standards for both internal and customer flights, providing strategic oversight as we prepare for global scale. What You'll Do:

  • 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

    • What You'll Bring:

  • 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

    • Bonus Points If You've:

  • 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

    • Want to join our mission? Apply to learn more!

    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.

    Skyways
    Skyways

    Skyways is developing fully autonomous unmanned aerial vehicles (UAVs) aimed at transforming air transportation. Targeting both commercial and defense markets, Skyways blends innovative design with real-world application, having already built and flown aircraft in collaboration with customers and government partners.

    Founded
    Founded 2017
    Employees
    1-10 employees
    Industry
    Aerospace & Defense
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