Flight Club

After leaving Obi in 2021, I decided to give myself some time to explore various projects as an independent contractor. This period allowed me to work on a few exciting ventures before committing to my next full-time role. One of these projects led me to Entourage Flight Club (EFC), a members-only private aviation club offering exclusive flights between New York City and Los Angeles on customized Airbus A319 aircraft. My journey with EFC began in mid-2022, when I was brought on board to lead the development of their digital platform as Chief Digital Officer.

obi's pitch deck at the time (july 2017)

The Genesis of Entourage Flight Club

Entourage Flight Club was the brainchild of Jeff Irvine, a seasoned entrepreneur I had previously collaborated with on another project called Loot. Loot was an AR-based app that allowed users to collect virtual rewards in the physical world, but the focus soon shifted to Jeff’s primary venture—Entourage Flight Club. The concept was simple yet ambitious: retrofit an Airbus A319, which typically accommodates around 150 passengers in an economy layout, to carry just 28 members in a luxurious, first-class setting. This transformation would include fully lie-flat seats and a lounge area in the back, all designed to offer an unparalleled private aviation experience.

Jeff reached out to me after our successful collaboration on Loot, inviting me to take on the role of Chief Technology Officer at Entourage. However, I was initially hesitant. While I had a solid understanding of technology, I didn't feel my technical skills were sufficient to fulfill the responsibilities typically associated with a CTO role. I expressed my concerns to Jeff, and he reassured me that my role would be more focused on product strategy and overseeing a team of developers, rather than handling the technical development myself. With that understanding, I accepted the offer, and my title was later adjusted to Chief Digital Officer to better reflect my responsibilities.

Navigating the Complexities of Aviation Technology

One of the first challenges I faced was understanding the highly regulated nature of the aviation industry. During my initial meeting with Yves Levine, a prominent aviation executive and co-founder of EFC, he emphasized that the aviation industry is the second most regulated industry in the world, second only to nuclear energy. This meant that every aspect of the technology we were developing had to comply with stringent regulatory standards, adding a layer of complexity I had never encountered before.

To familiarize myself with the industry, I immersed myself in learning about aviation regulations and the various third-party systems that power the world of aviation. This involved not only understanding U.S. aviation law but also global aviation standards, as EFC’s operations would eventually expand beyond domestic flights. I quickly realized that building the technology for EFC would require a deep understanding of these regulations, particularly regarding the integration of various systems.

Building the Platform

The core of my role at EFC was to develop a member booking app that would serve as the primary platform for our users. This app needed to allow members to sign up, manage their accounts, book flights, and interact with the club. Additionally, the app would need to handle complex functionalities such as guest management, seat selection, and payment processing, all while ensuring compliance with aviation regulations.

To kick off the development process, I began by identifying the key systems we would need to integrate. One of the most critical components was the Passenger Service System (PSS), which handles flight scheduling, pricing, and the booking process. After evaluating several options, we decided to partner with Travel Technologies Interactive (TTI), a French company based in Toulouse. Their PSS was not only robust but also compliant with the necessary regulations, making it the ideal choice for our platform.

With the PSS in place, I moved on to the design phase. I personally handled the wireframing and design of the app, ensuring that every screen was meticulously planned to avoid any unnecessary redesigns down the line. My goal was to create a seamless user experience that would make booking a flight with EFC as simple and intuitive as possible.

Once the designs were finalized, I collaborated with a development team to bring the app to life. For this, I chose to work with Iterators, a development firm based in Warsaw, Poland, with whom I had previously worked closely during my time at Obi. Their quote was reasonable, and given our successful past collaborations, I was confident they were the right team for the job. We established a master service agreement, and the development process was underway.

Overcoming Challenges and Moving Forward

Building a digital platform for a private aviation club is no small feat, especially in an industry as regulated as aviation. Throughout the process, I encountered numerous challenges, from understanding the intricacies of aviation regulations to ensuring the app was designed with scalability and user experience in mind. Despite the complexities, I found the experience incredibly rewarding, as it pushed me to expand my knowledge and skills in ways I hadn’t anticipated.

Looking back, my time with Entourage Flight Club was a pivotal moment in my career. It not only allowed me to apply my expertise in product strategy and digital design but also exposed me to the fascinating world of aviation. The project reinforced the importance of adaptability and continuous learning, especially when navigating unfamiliar industries. Ultimately, the platform we built laid the foundation for EFC’s operations, enabling them to offer a unique and luxurious travel experience to their members.

This case study reflects my journey from initial hesitation to confident leadership in developing a complex, regulated digital product. It serves as a testament to the power of collaboration, the importance of understanding industry-specific regulations, and the value of a well-executed digital strategy in bringing a visionary concept to life.

Thank you for reading.