Head of Customer Success
Austin, TX
Executive – Leadership /
Full-time /
On-site
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
The Head of Customer Success will shape how our customers succeed with our technology. This is not a reactive support function. It is about building long term partnerships, making deployments seamless, and ensuring that our aircraft become an indispensable part of our customers’ operations.
You will be Skyways’ external face, working closely with commercial and government users, training operators, integrating our systems into complex environments, and listening carefully to their needs. You will turn those insights into action by bringing them back to the engineering and product teams, closing the loop between customer experience and technical development.
This is a role for someone who thrives on problem solving, enjoys working directly with people, and wants to be on the front lines of bringing a brand new form of transportation into the world.
What You’ll Do:
- Build and lead the customer success function at Skyways.
- Develop and manage onboarding processes that ensure customers adopt and integrate Skyways products effectively.
- Establish key metrics and success criteria for customer outcomes and track performance against them.
- Spend meaningful time in the field with customers, traveling to sites to understand operations and ensure our aircraft fit seamlessly into their workflows.
- Act as a trusted partner to customers, solving problems with empathy and urgency.
- Bring customer insights back into Skyways to help shape product and engineering decisions.
- Represent Skyways with external agencies and partners, ensuring compliance and alignment.
What You’ll Bring:
- 8+ years of customer success, account management, or related experience in a technical or complex product environment.
- Background in aviation, drones, or aerospace.
- Clear and approachable communication style, with the ability to connect with both operators in the field and executives in the boardroom.
- A problem solving mindset, resourcefulness, and a calm presence under pressure.
- Willingness to travel regularly to customer sites while thriving in a role that balances fieldwork with strategy.
Bonus Points If You Have:
- Experience working with government or enterprise customers.
- Startup experience scaling customer success from the ground up.
- History of building customer facing teams in fast moving startups.
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.
