Increasing Merchant Retention by Rethinking Upside Payments

Upside Pay at the Pump

Pay at the Pump transformed Upside from a receipt-scanning cashback app into a real-time mobile payment platform at the pump.

Impact

Reduced payment
friction at the pump

-45% Merchant churn

Established a foundation
for Pay-with-App

The Problem

Merchant

  • Upside revenue blended into normal fuel sales, making ROI difficult to see
  • Monthly invoices were highly visible, making the product feel like an expense
  • Merchants struggled to clearly connect Upside to incremental growth

Consumer

  • Cash back felt delayed and disconnected from the purchase
  • Receipt uploads introduced unnecessary friction after fueling
  • Pump errors were confusing and difficult to resolve in real time

The Solution

Find station → Select pump → Activate → Fuel → Instant cash back

Offer Hub

Offer explanation

Pump selection

Confirm details

Finding the Right Pump Selection Pattern

We explored multiple interaction models to minimize cognitive load while standing at a pump.

Carousel

Keypad

Wheel picker

Grid

Final Pump Selector

We chose a simple tap-based selector that minimized decision time and scaled easily for stations with many pumps.

Final Pump Selector

Designing for Real-World System Constraints

Pump availablility

Pending charges

Payment validation

Unlocking the pump

These constraints shaped the order of the experience and prevented pump conflicts. Ultimately, we chose to have users select a pump first, reducing friction and ensuring the pending charge only occurred once a pump could actually be secured.

Select Payment then Pump

Select Pump and Payment Together

Select Pump then Payment
(Final design)

A New Way to Transact

We introduced clear "Pay with app" labeling throughout the experience to educate users. The label helped signal a shift from the traditional receipt-scanning flow to a new model where customers could pay for fuel directly in the app.

Offer Hub

Explainer Screen

Select Grade Screen

Expanding the Merchant Platform

To support real-time payments, we introduced new merchant features that allow stations to:

Select payment frequency
Connect bank accounts
Monitor transaction activity
Upside Dashboard Add a Bank Account

Dashboard Add Bank Account (New)

Upside Dashboard Payment Frequency

Dashboard Payment Frequency (New)

Outcome

Impact

  • Transformed Upside from a receipt-based cashback app into a mobile payment platform
  • Increased merchant engagement and strengthened the value proposition for partners
  • Simplified the customer experience by removing receipt uploads

Next Steps

  • Allow users to pre-select a fuel amount
  • Improve pump discovery and availability clarity
  • Better explain authorization holds
  • Provide clearer recovery paths when pumps fail