Head of Flight

At Skyways, we are building a new form of air transportation—what some call the flying car. Backed by fresh funding and a major STRATFI contract from the U.S. Air Force, we’re uniquely positioned to lead the next wave of aviation innovation. Our fully autonomous unmanned aerial vehicles (UAVs) represent a breakthrough opportunity to move goods—and soon, people—in ways that are faster, safer, and more efficient than ever before. Unlike anyone else in the industry, our strategy blends rapid iteration with real-world deployment, and it’s already paying off.

Skyways is a fast-growing startup based in Austin, TX, supported by top Silicon Valley investors including Y Combinator. Though we’re early-stage, our vehicles are already in production and in the hands of paying commercial customers (see here and here). With robust financial backing and government partnerships accelerating our momentum, there’s never been a better time to join us and help build the future of transportation!

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.

• 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.

• 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.

• 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.

• 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!

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.