This case study highlights the research and design journey behind 'PAIR,' an app designed to assist new and maker business owners with receipt management. The project involved user research, product design, and the development of an iOS app to showcase to potential clients.
Date
Feb - May 2024
Role
Product Designer
Company
DCC Technologies
Problem
A 2024 Bloomberg Tax survey found that 82% of small business owners acknowledge receipt management as one of their most significant administrative challenges, with the average entrepreneur spending upwards of 80 hours annually on receipt-related tasks.
Small companies lose an average of $12,000 annually due to mismanaged receipts and expense documentation
DCC Technologies, led by entrepreneur Chris Litwin, approached us with firsthand knowledge of these challenges. Chris envisioned a solution that would force business owners to organize their receipts on the go, which would help decrease the stress and complications of tax season. We were given the following constraints:
Retain the PAIR name and logo, designed by Chris’s daughter.
Build for iOS compatibility.
Develop a functioning app to support investor presentations.
Challenge
Small business owners in this situation often have three defining characteristics:
Minimal interest in finance: Managing receipts often takes a backseat to daily operations
Mixing personal and business expenses: Requires entrepreneurs to sort through the individual items in receipts, significantly increasing the financial upkeep workload
Limited time: Most business owners hold off on organizing finances until tax season, creating last-minute stress and unchecked information.
How might we streamline business expense tracking and encourage consistent habits to prevent tax season backlogs?
Solution
PAIR (Producing Automatically Indexed Receipts) integrates receipt organization into business owners’ daily operations—making it as seamless as checking your messages.
Research
Our journey with PAIR began with a straightforward, yet challenging prompt from Chris:
“I want an app that FORCES business owners to manage their receipts when they get them.”
This guided our exploration into how to make receipt management an integral part of the daily routine for business owners. To build a targeted solution, we identified two specific research objectives:
Objectives
Understand the stakeholders within the business context
Understand current receipt management practices, especially what causes owners to fall behind on managing business expenses.
Synthesis
We analyzed the data from user research to identify common pain points and patterns. This synthesis helped us better understand the challenges small business owners face with receipt management and informed the direction of our design decisions.
Stakeholder Map
There is a complex web of actors that are involved in the receipt management process. Stakeholders included business owners, federal and state tax agencies, bookkeepers, CPAs, and other vendors.
Mind Map
In the first round of affinity diagramming, we shared findings from individual research efforts, creating a mind map gave us a shared, high-level understanding of the problem ecosystem.
User Flows
To delve deeper, we analyzed user workflows to understand the journey from point of purchase to potential breakdowns. We created five distinct workflows, each representing varied receipt preferences, upkeep habits, and collaboration needs. By merging these individual workflows, we constructed a master workflow that captured the overarching organization processes of the business owners we interviewed.
Affinity Diagramming
In a second round of affinity diagramming, we synthesized our findings from the workflows to extract actionable insights, setting a foundation for our ideation phase.
Insights
"I need flexibility when manipulating data"
"I need an external trigger in order to start organizing"
"I mix up business and personal expenses a lot"
"I want to store my digital and physical receipts in the same place"
Ideation
Our ideation phase was driven by four main insights. We started with a "Crazy 8s" exercise for rapid brainstorming, generating over 50 ideas—ranging from smart wallets to parrots on the shoulder— to also experimenting with the "Worst Possible Solution." The best ideas were made into storyboards.
We narrowed down our ideas based on client feedback, user feedback, and a team vote. By the end,
we identified three main themes that our users were highly interested in and that no competitors addressed collectively.
Prompt users to organize expenses immediately
Users need an external trigger in order to form the habit of organizing frequently.
Sort expenses into relevant categories
Users primarily want to organize purchases into personal and business expenses while they still remember. Additionally, they value the ability to categorize expenses by business and assign items to the appropriate IRS categories.
Capture and transfer itemized data into a centralized platform
This removes the need for a last-minute scramble of printing bank statements, downloading digital receipts, and scavenging for physical receipts.
User Testing
Our first lo-fidelity flow included a physical scanner for receipts and a "Money Pool" incentive concept, where users could win back part of their subscription fee if they organized receipts on time.
When testing these prototypes with small business owners, we noticed a lot more negative feedback than before. Between our ideation and prototyping stages, there seemed to be a disconnect.
These new usability testing insights raised questions about the fundamental need for our product and prompted us to rethink our approach.
Reframing
We observed that negative feedback primarily came from business owners in the digital sphere or those with years of experience.
While our client initially believed this issue affected all small business owners, we discovered that the problem was more specific to a niche yet growing demographic: small new or maker business owners with limited financial expertise.
With a narrower focus on our target audience, we refined our design approach to better address their unique needs.
Up until this point, we focused heavily on finding ways to "force" users into action. However, after further conversations with our target audience, we learned that users are willing to sort receipts as long as they don’t perceive the process as tedious. On the other hand, no matter how much we try to push them, they won’t engage if they feel the process will be too time-consuming. Armed with this new information, we focused on simplifying the flow and reducing the steps required to complete tasks.
At this stage, we also recognized that several of our client’s initial demands weren’t feasible based on user feedback. Two major assumptions were overturned:
Users don’t want to be forced and prefer gentle reminders
Users are not opposed to scanning their receipts
Shifting from Client Vision to User Needs
Users want the solution fully digital
Chris didn't think a phone's scanning function was robust enough. However, business owners expressed concerns about using additional hardware, so we removed the physical scanner. Instead, we focused on a streamlined digital experience with enhanced mobile scanning capabilities.
Utilizing insistent notifications
We found that while external prompts were helpful, monetary incentives felt demanding and stressful. We simplified notifications to gently remind users to manage receipts without creating pressure.
Visual layout of the sorted receipt
Through A/B testing, we experimented with different layouts for displaying itemized lists. This helped us understand user preferences for viewing categorized receipts and the final organized screen.
Easy to parse
Alternating colors can look outdated
Brand names are unnecessary
Cleaner visual layout
Looks more familiar (Excel)
View the original receipt with the option to filter
Sorting Interface
Initially, we used toggle buttons for sorting, but testing revealed that these were unintuitive for our older user base. We then implemented a step-by-step interface with clear visual guidance, reducing the need for an onboarding tutorial. This simplified approach allowed users to navigate the app seamlessly each time they sorted expenses, improving overall usability and satisfaction.
Doesn't take much space
Not intuitive for older users
Confusion on where to tap
Completion button being at the same place is confusing
Buttons are not intuitive
Too much green
Easily seen instructions
Button hierarchy
Hides illegal moves
Our vision for PAIR goes beyond its initial release, with a roadmap dedicated to continuous innovation to meet the evolving needs of maker business owners. Key next steps include:
Continued Usability Testing and Iteration
We remain committed to user-centric design by conducting regular usability tests with our target audience. This feedback will help us identify pain points, uncover opportunities for improvement, and ensure PAIR stays intuitive and aligned with users' needs. Our iterative approach will allow us to refine existing features and introduce new functionality based on real user insights.
Explore Analytics and Collaboration Features
To empower business owners with data-driven insights, our next priority is integrating robust analytics for tracking spending patterns and identifying cost-saving opportunities. We will also introduce collaboration features, such as data-sharing with CPAs and bookkeepers and seamless export options to accounting software like QuickBooks or Xero, to streamline reconciliation and ensure tax compliance.
Expand Feature Set Based on User Feedback
We will continue to enhance PAIR based on user feedback, prioritizing features that add value. Potential updates include OCR for improved data extraction, integration with third-party tools, and support for multiple languages and currencies. By staying responsive to user needs and industry trends, we aim to make PAIR an indispensable tool for maker business owners globally.
Reflections
Working on PAIR was an incredibly rewarding experience, and I’m grateful for the opportunity to collaborate with such a dedicated team, advisor, and client. Reflecting on the process, our team faced significant challenges, particularly when user tests didn’t validate some of our initial design assumptions. One major hurdle was aligning with our client’s request to "force" users into sorting receipts. His suggestions, such as persistent notifications and screen blocks, clashed with technical limitations in iOS.
This project taught me the importance of balancing client expectations with user needs. While clients often have specific ideas, understanding and addressing users’ pain points is key to creating a product that truly resonates. It reinforced my belief that user-centric design is essential—not just for a product’s success, but for creating solutions that genuinely improve users’ lives.
