Redesigning the Repayment Journey with a Trust-First Approach

ROLE: Lead Product Designer

Company: Oakbrook Finance

TIMELINE: 1 Month

TEAM: Product, Engineering, Compliance and Operations

Oakbrook Finance, a fintech lending platform, faced a critical challenge: its existing card payment flow was unreliable and confusing, leading to high rates of failed one-off repayments. This directly resulted in increased customer arrears and ballooning support costs. A new, more trustworthy repayment journey was needed to address these issues head-on.

Summary

Oakbrook Finance’s one-off repayment flow was unreliable and confusing, leading to failed payments, increased arrears, and rising support costs. I led the redesign of the repayment journey, introducing a trust-first, step-by-step experience that guided customers through payments and reduced anxiety.

Key outcomes:

  • £376,000 in repayments processed within six months

  • 37% increase in repayment success rate

  • 28% reduction in support tickets

  • +1.5 point increase in post-payment CSAT

The Challenge: Building Confidence in Payments

Repaying a loan should feel straightforward, but the existing card payment flow caused confusion and stress. Customers were unsure if their payment had gone through, while support teams were overwhelmed resolving errors.

My goal was to create a seamless, trustworthy payment experience that reassured customers at every step while reducing operational burden.

Understanding Customers

I led a discovery phase combining qualitative and quantitative research:

  • Reviewed hundreds of support tickets to identify pain points

  • Analysed payment funnel data to see where users dropped off

  • Conducted interviews with five borrowers to understand concerns

Key insights from research:

  • Anxiety, not technical complexity, was the main barrier. Customers feared payments failing and losing control over their money.

  • Step-by-step guidance reduces uncertainty. Breaking the payment process into clear stages reassured users.

  • Clear communication builds trust. Microcopy explaining what happens next eased customer concerns and reduced support contacts.

Designing a Trust-First Payment Flow

Using these insights, I created prototypes that emphasized clarity, reassurance, and simplicity:

  • Step-by-step process: Users were guided through each stage, seeing exactly what would happen before taking action

  • Transparent handoff screens: Reassured users during bank connection and payment confirmation

  • Supportive microcopy: Changed generic messages like “Processing” to “We’re securely linking to your bank”

  • Iterative testing: Validated prototypes with users to ensure clarity and confidence

This approach transformed the repayment journey into a calm, predictable, and trustworthy experience.

Outcomes & Impact

The redesigned repayment flow delivered measurable benefits:

  • £376,000 in repayments processed within six months

  • 37% increase in repayment success rate

  • 28% reduction in support tickets

  • +1.5 point increase in post-payment CSAT

Customers felt more confident completing payments, while the operations team could focus on strategic work instead of troubleshooting failures.

Reflection

This project reinforced the power of trust-first design in fintech. By observing users, addressing emotional barriers, and embedding guidance throughout the flow, I was able to transform a stressful payment experience into one that was reliable and reassuring.

It highlighted that thoughtful UX can directly improve customer satisfaction, operational efficiency, and financial outcomes — turning a critical friction point into a positive touchpoint.

© Ryan hewitt 2025

© Ryan hewitt 2025