Head of Flight

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.

What You'll Do:

• Provide strategic and operational oversight for all flight activities.
• Serve as the primary liaison between Skyways, our customers, regulatory bodies, and military stakeholders.
• Coordinate across Skyways teams to align on all flight-related initiatives.
• Lead, mentor, and develop the flight team.
• Oversee test scheduling, aircraft planning, and personnel management.
• Gain deep knowledge of Skyways aircraft to inform flight ops.

What You'll Bring:

• Significant experience (10+ years implied) leading flight operations and/or flight testing in an aviation environment.
• Deep understanding of aviation principles and flight dynamics, demonstrated through relevant experience and/or certifications.
• Proven experience engaging with and navigating aviation regulatory bodies.
• Demonstrated ability to build, mentor, and manage high-performing teams.
• Strong, independent problem-solving capabilities.
• A genuine passion for hands-on work and continuous learning within the aviation field.

Bonus Points If You've:

• Held high-level management positions at cutting-edge aviation companies.
• Experience in the space, airlines, or automotive industries, especially leading complex engineering teams.
• A background as a military pilot transitioning to the private sector.
• Experience with organizations like United Airlines (organizational emphasis) or those leading flight at advanced composite manufacturers.

Benefits at Skyways:

• Health coverage: medical, dental, and vision insurance
• Time to recharge: paid time off and holidays
• Planning ahead: 401(k) retirement savings
• Peace of mind: life insurance coverage
• Shared success: stock options for every employee
• Extra perks to make the workday easier and more enjoyable

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.