TailHail is a global private aviation membership platform that lets members charter private flights, join shared flights, and access empty-leg deals - driven by an ethos of bringing a more transparent, flexible alternative to traditional private aviation.

client

TailHail

year

'21

timeframe

4 Months

UI

UX

APP

TailHail App

Problem

Private aviation platforms are traditionally opaque and fragmented. Pricing is unclear, booking flows are inconsistent, and most experiences are built for industry insiders rather than everyday travelers. First-time customers struggle to understand their options, while experienced travelers face friction navigating outdated interfaces built around legacy workflows. The challenge was to design an experience that felt modern, intuitive, and trustworthy... positioning TailHail as a lifestyle-driven alternative to traditional charter services, rather than another opaque booking tool.

Discovery

We began with a structured discovery phase to align the team around business goals, user needs, and constraints. Through collaborative workshops, we defined core user segments, mapped end-to-end journeys, and identified pain points across search, booking, and account management. This grounded the value proposition and helped establish a focused MVP scope, so every design decision that followed was rooted in real user needs and technical feasibility rather than assumption. These insights directly shaped the experience strategy. User flows were designed to reduce cognitive load by breaking complex tasks into clear, sequential steps. Personas guided feature prioritization and content hierarchy, ensuring the interface worked equally well for seasoned private travelers and users completely new to the space. This gave us a strong UX foundation to build on before moving into detailed interface design.

Flight Search, Search Results, Flight Itinerary & Payment

Example User Persona

Example User Journey Mapping

Example Empathy Mapping

Multiple TailHail App UI Screens

TailHail Analytical Dashboard Snippet

Design & Iteration

I led the design process from low-fidelity wireframes through to high-fidelity UI, iterating closely with stakeholders at each stage. Early wireframes let us validate layout, navigation, and core flows quickly and cheaply, while high-fidelity designs explored visual direction, usability patterns, and edge cases in detail. Key experiences included home and airport search, booking and itinerary management, quotes and payments, and membership selection. Design decisions throughout were driven by UX rationale rather than aesthetics alone. Interface elements were prioritized based on user intent, error states were considered from the outset rather than bolted on later, and flows were continually refined to reinforce clarity and trust. Regular review cycles gave the team room to challenge assumptions and push the experience forward, even in the absence of formal usability testing.

I led the design process from low-fidelity wireframes through to high-fidelity UI, iterating closely with stakeholders at each stage. Early wireframes let us validate layout, navigation, and core flows quickly and cheaply, while high-fidelity designs explored visual direction, usability patterns, and edge cases in detail. Key experiences included home and airport search, booking and itinerary management, quotes and payments, and membership selection. Design decisions throughout were driven by UX rationale rather than aesthetics alone. Interface elements were prioritized based on user intent, error states were considered from the outset rather than bolted on later, and flows were continually refined to reinforce clarity and trust. Regular review cycles gave the team room to challenge assumptions and push the experience forward, even in the absence of formal usability testing.

Outcome

The result was a coherent, end-to-end MVP experience that gave TailHail a clear, scalable foundation to build from - turning a category known for opacity and inconsistency into something that felt modern, self-explanatory, and trustworthy from first search to final booking. By grounding every flow in real user segments and validated journeys rather than industry convention, the design gave both newcomers and experienced private travelers a consistent, low-friction path through search, booking, and membership. The structured, iterative process also left the team with a shared, well-reasoned rationale behind every key screen; a foundation that made it easy to prioritize what shipped in the MVP and to keep building with confidence afterward. Note - credit to Boxmodel and TailHail for allowing this project to happen.

The result was a coherent, end-to-end MVP experience that gave TailHail a clear, scalable foundation to build from - turning a category known for opacity and inconsistency into something that felt modern, self-explanatory, and trustworthy from first search to final booking. By grounding every flow in real user segments and validated journeys rather than industry convention, the design gave both newcomers and experienced private travelers a consistent, low-friction path through search, booking, and membership. The structured, iterative process also left the team with a shared, well-reasoned rationale behind every key screen; a foundation that made it easy to prioritize what shipped in the MVP and to keep building with confidence afterward. Note - credit to Boxmodel and TailHail for allowing this project to happen.