Alex Di Guardo

Flexible Bookings

How reducing booking anxiety drove
£4 million in annual incremental revenue

This case study is written as a behind the scenes story to give you a better idea of what it's like to work with me, with a focus on decision making, stakeholder alignment and trade-offs required to deliver the initiative.

💼 Cottages.com

🕰️ 2025 - 2026

🧑🏻‍🎨 Product Designer

In a nutshell...

🎯 Opportunity & business goal:
Increase booking confidence by offering a paid Flexible Cancellation option, while growing overall revenue per visitor without causing disproportionate conversion loss.

💡 My approach & role:
• I led the design direction and strategic framing for Flexible Cancellations, operating at product-area level and aligning with designers across the booking journey to ensure a consistent end-to-end experience.

• I defined the North Star, aligned Product, Engineering, Legal, Marketing and Commercial stakeholders, and guided decisions that balanced customer trust, commercial impact and experience risk.

📈 Success metrics:
• Estimated £4 million annual incremental revenue
• 23% attach rate (vs 15% target)

Rapid concept prototyping was key

Leveraging Figma Make to accelerate stakeholder buy-in
and support confident decision-making


In the following chapters, I'll walk through how I led the design to this point

Customer Journey Management

Understanding the full journey and avoid working in silos

For big projects, rather than designing for isolated parts of the journey, it's my standard practice to run cross-squad workshops at a product level to identify the impacted areas of the journey.

This also helped aligning design, product and tech towards the same goal, across the whole experience.

Crucial areas I identified (marked in red) as affected by the introduction of Flexible Cancellations

Iterations & Key Decisions

From MVP to North Star

At each stage, I addressed a specific risk and used research and behavioural insight to guide decisions.

While overall conversion decreased slightly, this was an explicitly accepted trade-off,
with leadership prioritising higher value bookings over conversion

Combining user testing with AI synthesis

My approach



Key learnings



Examples of quotes showing users' understanding and preferences

Challenges & risks

The primary risk was introducing a price sensitive decision on the Property Description Page, historically the most fragile part of the funnel.

Despite this, I made the call to proceed with controlled experimentation rather than defaulting to safer but lower impact options.

Graph emphasising the risk of introducing changes to a delicate Property Description Page

Stakeholder management & trade-offs

3 big diverging opinions emerged around pricing, level of details and compliance:

Each decision balanced user confidence and commercial impact resolved through experimentation

What didn't go as expected

and how I turned it around

These were resolved in the final iteration by setting a default option
and displaying explicit refund amounts rather than just legal terms



Final results

While overall conversion decreased slightly, this was an explicitly accepted trade-off,
with leadership prioritising higher value bookings over conversion

Updating the Design System

Once a clear winner is defined,
I proceed with the design system update

Example of how the Booking Panel component evolves in the Design System

Next Steps

1️⃣ Work with marketing to raise awareness about Flexible cancellations on site and off-site to mitigate the “surprise effect” and regain conversion

2️⃣ Scale the solution across the other brands we own at Awaze

3️⃣ Measure the long term effects on revenue

Want to know more? Reach out!