How Embracing Chaos in Marketplace Led to Order

At Wingly, where hobby pilots offer flights to adventure-seeking passengers, we faced a critical challenge: 37.5% of our bookings were falling through. Pilots were refusing these bookings due to issues like aircraft unavailability, poor weather conditions, or personal scheduling conflicts. Each declined flight meant disappointed customers and lost revenue.

As the Product Designer, I was tasked with solving this puzzle. The catch? We couldn't simply push pilots to accept more flights – safety always comes first in aviation.

When conventional fixes fell short, we embraced an unconventional approach. Instead of preventing declines, we found a way to rescue these "failed" bookings. The result? An innovative feature that boosted our success rate by +5% and saved €40,000 in just the first months.

🎯 The Challenge

• Reduce 37.5% booking failure rate

• Innovate within strict safety & operational constraints

🧑‍🧑‍🧒‍🧒 Users and Stakeholders

The project involved three key groups:

• Passengers seeking unique flight experiences

• Pilots offering flights and seeking more bookings

• Wingly's management and operations team

👨‍💻 Role and Responsibilities

As the Product Designer, my responsibilities encompassed:

• User research & data analysis

• Project planning & stakeholder communication

• User flow & UI design

• Content strategy & localisation

• KPI setup & tracking

🔁 The Process

We followed the Double Diamond methodology: Discover & Research, Concept Development & Planning, Design & Development, and Release & Observe. From the outset, we agreed that building an MVP version was crucial. Our goal was to launch quickly to validate the feature's effectiveness, then iterate based on positive signals. All of this needed to be completed before the high season for flight activities began, putting us under tight time constraints.

Discover & Research

In this phase, we focused on answering key questions:

• How many bookings/GMV could the feature save?

• How would passengers react to a new pilot after an initially failed booking attempt?

• What could hinder the success of this feature?

Our research revealed:

• 81% of booking failures occurred more than 48 hours before the flight time

• 83% of passengers were open to rebooking with different pilots

• We estimated a potential GMV recovery in the range of a five-digit number within the first few months.

To gather more insights, we launched a survey on the Flight checkout confirmation page, asking passengers: "Would you be interested in being contacted by other pilots in the area if the initial pilot cannot fulfil your flight?" 80% of respondents expressed interest, although we noted that the survey was optional with a 50% response rate.

Using Metabase, I built a dashboard that provided crucial data:

• 81% of bookings failed more than 48 hours before the flight date

• We established a 48-hour "imaginary" time limit, recognising that last-minute flights were unlikely due to pilots' preparation needs

• 60% of already accepted bookings that were cancelled could potentially be covered by our new feature

Our research indicated that up to a five-digit sum in GMV could be saved. However, we recognized the need to ensure a high volume of bookings going through the feature funnel to achieve a meaningful business impact.

🔼 Flight Purchased Confirmation page

🔼 Metabase Dashboard: Booking Failure Analysis

After launching the product, we conducted additional research to refine our approach:

• We noticed that around 20% of bookings were expiring without being picked up by pilots.

• We launched a survey to pilots to understand if they were using the feature and if they had heard about it.

• We learned that many pilots knew about the feature but hadn't tried it yet, or if they had tried, they had only answered a few requests.

• This insight was one of the reasons we decided to open up requests to other nearby airfields, maximising the number of pilots we could reach and giving them more opportunities.

👨🏼‍🏫 Concept & Planning

In this crucial phase, we laid the groundwork for our innovative solution to Wingly's booking failure challenge. Our process involved several key steps:

Concept Creation and Alignment

1. Feature Flow Development: I created a detailed feature flow, envisioning a secondary marketplace where pilots could pick up failed bookings.

2. Team Alignment: Through collaborative sessions, we aligned the team and company on the feature idea, ensuring buy-in from all stakeholders.

3. Feature Journey Mapping: I drafted an initial feature journey, highlighting areas of complexity and key considerations, such as the process for notifying pilots of new opportunities. This visual aid facilitated in-depth discussions among product & design, development, and operational teams.

🔼 Feature Journey Map: Pilot Takeover Flow

Project Structure and Timeline

During the conception phase, we identified the need for a phased approach to ensure success:

1. Pilot Pre-launch

2. Official Launch

3. Post-launch Adjustments

Throughout the process, I shaped the feature into a flow, made all the logic of how to display it to passengers and pilots, and ensured engineers could deliver the design and idea. As the sole product designer, I managed all design work while ensuring alignment between design, head of product, and operations teams.

Plan & Prioritisation

To guide our execution, we developed a detailed to-do list, breaking down each phase into specific, actionable tasks:

Pilot Pre-Launch

• Create a landing page for pilot feature subscription

• Develop and send a feature launch newsletter to pilots

• Gather pilot feedback on the upcoming feature

We prioritised the pilot pre-launch to ensure we had a good number of pilots already onboarded. This strategy was crucial to prevent wasting any bookings from day one of the official launch.

Official Launch

• Develop passenger flow: handover information, cancellation process

• Implement pilot flow: booking opportunity list and takeover functionality

• Rework the notification system

These elements were prioritised as they were essential for the feature to function effectively. We emphasised giving control to users and keeping them informed of the current status quo throughout the process.

Post-launch Adjustments

• Improvements after feedback

We planned for post-launch adjustments to be made based on real-world usage and user feedback. This approach allowed us to first confirm that the feature is working before investing too much time.

🔼 Project Tasks: Organised list of design tasks

Benefits of Our Structured Approach

This comprehensive planning allowed us to:

• Clearly define the scope of each project phase

• Ensure all team members understood their responsibilities

• Maintain focus on critical features for the MVP

• Plan for post-launch improvements based on anticipated user feedback

By breaking down the project into these specific tasks and phases, we were able to move quickly and efficiently, meeting our tight deadline while still delivering a comprehensive solution. This structured approach was crucial in navigating the complexities of the flight-sharing platform and addressing the unique challenges of our booking failure problem.

With our detailed plan in place, we were well-prepared to move into the Design & Development phase, confident in our strategy and aligned on our goals.

👨🏼‍💻 Design & Development

Our approach to designing and developing this feature was driven by the unique challenges of the flight-sharing context and Wingly's specific needs. We adopted an MVP (Minimum Viable Product) strategy, aiming to build, launch, and iterate quickly to maximise the testing period before the high season started.

Strategic Approach: MVP in Three Phases

1. Pilot Pre-Launch

2. Official Launch

3. Post-launch Adjustments

This phased approach allowed us to move fast while addressing the complexities of the flight-sharing platform.

Pilot Pre-Launch

Goal: Onboard as many pilots as possible before the feature went live.

Key actions:

• Designed engaging emails to introduce the new feature

• Created a landing page for pilots to set their preferences for requests

• Attempted to re-engage churned or never-activated pilots

Outcome: While reactivating churned pilots didn't yield significant results, we successfully captured 20% of active pilots.

🔼 Pilot Onboarding: Email

🔼 Pilot Onboarding: Landing Page Design

The email and landing page designs, as shown in Image 1, focused on clearly communicating the benefits of the new feature. We used a friendly, approachable tone and included step-by-step instructions to make the onboarding process as smooth as possible for pilots.

Official Launch

Challenge: Ensure passengers understand the rebooking process when their initial booking fails.

Key considerations:

• Integrate handover information seamlessly into the user journey

• Communicate clearly on the failed booking page

• Balance information density with user experience

Solution: We decided to communicate two primary points on the failed booking page:

1. Your booking with the initial pilot did not succeed

2. We are actively searching for a new pilot to fulfil your flight request

While this approach made it slightly harder for users to see an overview of flights in search, we determined it was the most effective solution given that users rarely have more than one active booking at a time.

🔼 Failed Booking Page: New pilot search ongoing

🔼 Failed Booking Page: New pilot found, accept pilot

As seen in Image 2, we designed a clear and reassuring interface for passengers when their initial booking failed. The messaging emphasises the opportunity to still have their flight fulfilled, maintaining a positive user experience even in a potentially frustrating situation.

Post-launch Adjustments

Based on user feedback and observed behaviours, we made several key adjustments. Our approach was twofold: first, we prioritised main flows to ensure users had more control, and second, we focused on areas with the highest opportunity to increase matching based on user feedback.

1. Edit Availability Feature:

   • Challenge: Passengers wanted to update their availability after the initial booking failed.

   • Solution: Implemented a feature allowing passengers to edit dates, providing more options for potential pilots.

2. Expanded Pilot Pool:

   • Challenge: Limiting rebooking to the initial airfield led to high expiration rates and missed opportunities for nearby pilots.

   • Solution: Opened up rebooking opportunities to pilots from nearby airfields, increasing the chance of successful matches.

🔼 Passenger flow: Update your flight availability

🔼 Passenger flow: Update your departure airfields

🔼 Passenger flow: Update refund date

🔼 Passenger flow: Redesigned new pilot search ongoing

🔼 Passenger flow: Redesigned new pilot found, accept pilot

❇️ Results & Impact

We closely monitored key metrics to gauge our solution's effectiveness and drive improvements:

• Match Rate: Successful rematches of failed bookings

• Request Response Rate: Pilot engagement with new opportunities

• Passenger Cancellation Rate: Ensuring new system didn't increase cancellations

• Overall Booking Success Rate: Our primary KPI

These metrics guided our iterations and led to impressive results:

• 5% increase in overall booking success rate

• 282 bookings recovered in two months

• A five-digit amount in GMV was saved.

• Increased pilot engagement on the platform

• Improved passenger satisfaction and trust

By focusing on these key indicators, we created a solution that not only addressed booking failures but also enhanced the overall user experience for both pilots and passengers on Wingly.

🔼 Impact Infographic: Key Metrics & Results

🧑‍🏫 Lessons Learned

• Short-term vs. Long-term Solutions: While this feature worked well, we recognise it should be a short-term solution. Our long-term focus should be on fixing the initial reasons for booking failures to ensure users don't have to go through a negative experience.

• Unique Industry Constraints: Wingly operates in a unique space where we can't be too pushy about flying due to safety concerns and promises made to EASA. This leads us to create unconventional solutions like fixing the aftermath of failed bookings.

🔮 Future Considerations

• Root Cause Analysis: While this feature successfully addresses the symptoms of booking failures, future work should focus on identifying and addressing the root causes of these failures.

• Expanding Pilot Network: Consider ways to increase the number of active pilots and their engagement with the platform to further reduce booking failures.

• Continuous Iteration: Based on the success of this feature, continue to iterate and refine the rebooking process to further improve user experience and booking success rates.

🎬 Conclusion

This project demonstrated how embracing an unconventional approach can lead to innovative solutions in complex marketplaces. By addressing the booking failure issue creatively, we improved user satisfaction and increased platform efficiency and revenue potential, setting a strong foundation for future enhancements to the Wingly platform.