Head of Customer Success

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

We are hiring a Director of Customer Success to build and lead the team that ensures our customers are successful with Skyways technology. You will own the post sale customer journey, from onboarding through long term support, helping our customers realize value quickly and consistently. This is a leadership role that combines relationship management, technical insight, and operational execution. You will work closely with engineering, product, and operations to make sure customer needs are not only met but anticipated.

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.
• Partner with engineering and product teams to relay customer feedback and influence product direction.
• Manage customer escalations and serve as the senior point of contact for strategic accounts.
• Create playbooks, best practices, and training resources to scale customer success.
• Foster long term customer relationships that drive retention, expansion, and advocacy.
• Collaborate with sales and marketing on renewals, upsells, and case studies.

What You’ll Bring:

• 8+ years of customer success, account management, or related experience in a technical or complex product environment.
• 3+ years in a leadership role building or managing customer success teams.
• Proven ability to develop processes, metrics, and strategies for customer adoption and retention.
• Strong communication and relationship management skills with both technical and executive level stakeholders.
• Experience managing escalations and turning around challenging customer situations.
• Operational rigor with an ability to design and scale repeatable processes.
• Familiarity with CRM and customer success tools such as Salesforce, HubSpot, or Gainsight.

Bonus Points If You Have:

• Aerospace, robotics, or defense industry experience.
• Experience working with government or enterprise customers.
• Startup experience scaling customer success from the ground up.
• Technical background or ability to understand engineering level discussions

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.