Head of Flight

At Skyways, we are building the future of air transportation with fully autonomous unmanned aerial vehicles (UAVs). Backed by significant funding, including a $37M STRATFI contract from the U.S. Air Force, we operate at the intersection of commercial and defense markets. We have designed, built, and flown aircraft with real customers and government partners, and are now entering the next phase of the company: scaling toward production.

Based in Austin, TX and supported by top investors including Y Combinator, Skyways blends rapid iteration with real world deployment. We design, test, and operate our systems in the field, then bring those learnings directly back into engineering and product decisions. As we grow, we are looking for builders and leaders who want real ownership, technical depth, and the opportunity to help take an aircraft from successful deployments to full production.

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::
• 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.