Austin, TX

Open Roles – Skyways /

Full-time /

On-site

At Skyways, we are building the next generation of autonomous air transportation. Our fully autonomous unmanned aircraft systems move cargo faster and more efficiently than traditional logistics networks.

Backed by strong investor support and a $37M STRATFI contract from the U.S. Air Force, we operate at the intersection of commercial logistics and national defense. Our aircraft are not just prototypes—we design, build, fly, and deploy them with real customers today.

Based in Austin and supported by investors including Y Combinator, Skyways combines rapid engineering iteration with real-world operations. As we scale toward larger deployments, we are looking for people who want to help build and operate the future of autonomous aviation.

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.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.