Staysure Quote Journey
Overview
Staysure’s online travel insurance quote journey was dated, cluttered and difficult to use on mobile. It also no longer reflected the brand or the wider digital transformation happening around it.
As UX Design Lead, I co-led its redesign with the then Head of Design, working alongside product, research and engineering. The new journey increased start-to-quote-to-sale conversion by 5%, auto-renewal by 10% and average order value by 2%.
Journey mapping and analytics revealed clear friction points:
Long, intimidating question sets
Confusion around cover types
High anxiety during medical screening
Poor mobile ergonomics
Language that felt formal and insurer-led
Drop-off wasn’t primarily about price. It was about uncertainty.
Customers were asking themselves:
“Am I covered properly?”
“What happens if I get this wrong?”
“Why are you asking me this?”
The redesign needed to reduce that uncertainty without weakening regulatory checks or accessibility. That meant changing the structure of the journey, not simply updating how it looked.
Categories
UX/UI
Design Systems
User Research
Client
Staysure
Date
2023
Old quote journey & new treatment
The quote journey price page
Our Figma atomic design system
Process
I co-led the creative and UX direction with the then Head of Design, working alongside product owners and the Director of Digital & Experience. Wunderman Thompson supported the research by interviewing customers, reviewing analytics and mapping where people dropped out or became confused.
The findings were consistent: the journey was too long, relied on insurance jargon and didn’t work properly on mobile. That gave us a clear set of priorities for the redesign.
We broke the journey into clearer, shorter steps with visible progression. Instead of overwhelming users with a long one-size-fits-all form, we introduced progressive disclosure — surfacing complexity only when relevant.
The redesign shifted from cluttered, multi-input screens to focused, single-task interactions. Mobile wasn’t treated as a breakpoint adaptation; it was the starting point.
We prioritised:
Large tap targets
Clear hierarchy - one or two questions per page, reducing cognitive load
Strong, singular primary CTAs
The result was a journey that felt guided rather than interrogative.
I led the creation of an atomic design system, working with a mid-weight designer. We built accessibility into the components from the start, then tested them in prototypes across mobile, tablet and desktop to make sure they worked in real journey layouts.
We built an interactive prototype and tested it with customers recruited by our research partner. Their feedback shaped the medical screening flow, wording and marketing proof points.
Once the design was validated, I worked with developers through delivery, checking the implemented journey against the designs and monitoring performance after launch.
Takeaways
Performance improved across the measures that mattered most:
5% increase in start-to-quote-to-sale conversion
10% increase in auto-renewal
2% increase in average order value
Staysure had record years in 2023 and 2024. The quote journey was one part of that wider performance, making it easier for more customers to complete a purchase. I wouldn’t attribute the company’s growth to a single project, but the conversion, renewal and order-value results show that the redesign made a measurable contribution.
One idea stayed with me from this project:
Most conversion problems are clarity problems.
Customers weren’t leaving because the product was wrong. They were leaving when the experience created doubt. Research helped us find those moments, simplify them and explain why information was needed. The design system gave us a consistent way to carry those decisions through the whole journey.
Staysure Quote Journey
Overview
Staysure’s online travel insurance quote journey was dated, cluttered and difficult to use on mobile. It also no longer reflected the brand or the wider digital transformation happening around it.
As UX Design Lead, I co-led its redesign with the then Head of Design, working alongside product, research and engineering. The new journey increased start-to-quote-to-sale conversion by 5%, auto-renewal by 10% and average order value by 2%.
Journey mapping and analytics revealed clear friction points:
Long, intimidating question sets
Confusion around cover types
High anxiety during medical screening
Poor mobile ergonomics
Language that felt formal and insurer-led
Drop-off wasn’t primarily about price. It was about uncertainty.
Customers were asking themselves:
“Am I covered properly?”
“What happens if I get this wrong?”
“Why are you asking me this?”
The redesign needed to reduce that uncertainty without weakening regulatory checks or accessibility. That meant changing the structure of the journey, not simply updating how it looked.
Categories
UX/UI
Design Systems
User Research
Client
Staysure
Date
2023
Old quote journey & new treatment
The quote journey price page
Our Figma atomic design system
Process
I co-led the creative and UX direction with the then Head of Design, working alongside product owners and the Director of Digital & Experience. Wunderman Thompson supported the research by interviewing customers, reviewing analytics and mapping where people dropped out or became confused.
The findings were consistent: the journey was too long, relied on insurance jargon and didn’t work properly on mobile. That gave us a clear set of priorities for the redesign.
We broke the journey into clearer, shorter steps with visible progression. Instead of overwhelming users with a long one-size-fits-all form, we introduced progressive disclosure — surfacing complexity only when relevant.
The redesign shifted from cluttered, multi-input screens to focused, single-task interactions. Mobile wasn’t treated as a breakpoint adaptation; it was the starting point.
We prioritised:
Large tap targets
Clear hierarchy - one or two questions per page, reducing cognitive load
Strong, singular primary CTAs
The result was a journey that felt guided rather than interrogative.
I led the creation of an atomic design system, working with a mid-weight designer. We built accessibility into the components from the start, then tested them in prototypes across mobile, tablet and desktop to make sure they worked in real journey layouts.
We built an interactive prototype and tested it with customers recruited by our research partner. Their feedback shaped the medical screening flow, wording and marketing proof points.
Once the design was validated, I worked with developers through delivery, checking the implemented journey against the designs and monitoring performance after launch.
Takeaways
Performance improved across the measures that mattered most:
5% increase in start-to-quote-to-sale conversion
10% increase in auto-renewal
2% increase in average order value
Staysure had record years in 2023 and 2024. The quote journey was one part of that wider performance, making it easier for more customers to complete a purchase. I wouldn’t attribute the company’s growth to a single project, but the conversion, renewal and order-value results show that the redesign made a measurable contribution.
One idea stayed with me from this project:
Most conversion problems are clarity problems.
Customers weren’t leaving because the product was wrong. They were leaving when the experience created doubt. Research helped us find those moments, simplify them and explain why information was needed. The design system gave us a consistent way to carry those decisions through the whole journey.
© 2026 All rights reserved
© 2026 All rights reserved
© 2026 All rights reserved