Director of Software

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 creating a new form of transportation to advance our civilization from Austin, Texas.

The Opportunity

As Director of Software, you will own the software behind Skyways aircraft flying real missions today.

You will lead execution across autonomy, SkyNav, and the internal tools that support flight operations, production aircraft, and customer deployments. This is a hands-on leadership role for someone who can set direction, build the team, create the roadmap, and still go deep technically when the hardest problems need direct ownership.

The role sits at the intersection of software, aircraft, operators, and customers. You will work closely with flight, hardware, manufacturing, and operations to turn real-world constraints into reliable software that scales from live deployments to larger autonomous fleets.

What You’ll Do:

• Own software execution and the software roadmap across autonomy, SkyNav, and the internal tools that support aircraft flying today
• Build, lead, and develop the software team, including hiring, performance, growth, and the tech-lead or management layer as the team scales
• Own org design for software, and be accountable for delivery, team health, and the software budget
• Act as a player coach. Write code, review code, and take on hard problems when needed
• Set technical direction through shipped systems and measurable outcomes
• Work directly with operators and customers to iterate based on live deployments and field feedback
• Partner tightly with hardware, flight, and manufacturing to ensure software and aircraft evolve together
• Improve reliability, performance, and maintainability as the fleet and customer base scale, * Experience supporting software on production hardware, flight systems, or safety-critical systems.

• Proven experience shipping and supporting complex production software systems
• Experience leading and developing software teams, including hiring and growing engineers, while staying close to the technical work
• Experience with autonomy, robotics, or mission planning systems
• Strong systems thinking across autonomy, frontend, backend, and infrastructure
• Comfort operating in environments where software meets hardware and real-world constraints
• Bias toward execution, ownership, and accountability
• Hands-on experience building with Python, C++, and JavaScript, * Startup experience scaling teams and systems while things are still evolving.
• Hands-on experience building with ROS, ElectronJS, Ardupilot, or Mavlink.