Expensly
Understanding Everyday Expense Tracking Behavior
Expense tracking often fails not because people lack tools, but because it doesn’t align with their real-world behavior. This project explores how business owners and entrepreneurs capture, organize, and retrieve financial information, where their process breaks down, and how insights from these behaviors can inform better design.
Role:
Led the end-to-end research and design process:
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Defining research objectives
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Conducting user interviews
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Analyzing behavioral patterns
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Synthesizing insights
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Applied these insights to inform UX flows, IA, wireframes, and interactive prototypes.
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Conducted usability testing to validate design decisions.
Click Me
This project demonstrates my ability to translate qualitative research into practical, high-impact product decisions.
Case Study
Understanding the Problem
Imagine searching for a receipt needed for a critical tax deduction, only to realize it’s lost or buried among dozens of emails and paper slips. This real-world challenge highlights a broader behavioral problem: how freelancers and small business owners capture, organize, and retrieve financial information in everyday life. To guide this query, i ask:
Research Question: How do freelancers and small business owners track and manage expenses, and at what points does the process fail in real-world contexts?
The Problem for small businesses during tax season:
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Expense tracking is fragmented and time-consuming, often relying on folders, email searches, and spreadsheets.
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Critical receipts are frequently lost, resulting in missed tax deductions.
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Manual tracking increases stress and is prone to human error.
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Existing digital tools often overwhelm users with unnecessary features, creating friction instead of support.
Problem Statement: How might we support freelancers and small business owners in capturing, organizing, and retrieving receipts efficiently, reducing stress and minimizing errors during tax season?
To investigate this problem, I conducted qualitative research with freelancers and small business owners to understand their behaviors, pain points, and unmet needs. Insights from this research directly informed the design of wireframes, prototypes, and interactive solutions. This case study walks through my process, from defining the problem and conducting research to synthesizing insights, iterating on designs, and validating solutions through usability testing.
Research Approach & Methods of Inquiry
Conducted 6+ semi-structured interviews with freelancers and small business owners. Focused on understanding daily routines, cognitive load during expense tracking, and common pain points.
Questions were designed to uncover not only what participants do, but why they make certain choices.
01: Interviews
Observed participants in real-life tracking situations, reviewing receipts, email organization, and spreadsheet usage, to capture workflow inconsistencies and breakdowns.
This helped identify the points where tracking habits fail and what environmental or contextual factors influence behavior.
02: Contextual Inquiry
Tested wireframes and interactive prototypes with 5 users to validate whether proposed designs addressed the real-world pain points identified in research.
Sessions focused on efficiency, error reduction, and cognitive load during receipt capture and retrieval.
03: Usability Testing
User Insight: Business Owners
I conducted 7 user interviews and observational studies with freelancers and independent contractors to understand their workflow.
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Interviews were chosen to capture nuanced behaviors and motivations not visible in analytics.
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Contextual inquiry allowed observation of habitual breakdowns that users could not verbalize.
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Usability testing validated whether solutions aligned with natural workflows rather than assumed workflows.
Key insights from this mixed-method research showed that users spend an average of 5+ hours/month organizing receipts. Some pain points include:
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Receipts are scattered across email, paper, and apps and sometimes it can be difficult to stay organized
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With busy business seasons, its easy to forget to track small purchases.
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With receipts and expenses scattered across apps, this can sometimes bring anxiety during tax season due to missing info.
User Persona
Jamie, 34 - Wedding Photographer
Freelance photographer who struggles to keep receipts organized while traveling for client work.
Core Needs:
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Capture receipts quickly on the go.
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Automatically categorize and organize expenses.
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Reduce stress and errors during tax season.
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Get a clear monthly overview of spending.
Pre-Testing and Pre-Validation: Version 1
The initial prototype version below was designed with regular users in mind; people who want to track their own everyday expenses, not businesses or freelancers. However, upon further research and validation with business owners, insights provided clearer direction for which user groups will value this product the most.
Manual receipt capture and simple categorization.
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Focused on mobile-first UX with a central “Upload receipt” button.
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Users could review and edit categories manually.
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Key Insights That Shaped the Product
Testing with freelancers and consultants revealed that:
Manual entry and categorization were time-consuming and error-prone.
Users wanted automatic extraction of receipt details and found it more useful for business expenses.
Email receipts require consolidation.
Additional needs included monthly summaries, alerts for missing receipts, and reminder for tax season.
Validation & Iteration
Based on feedback, we decided to introduce automated OCR scanning and AI categorization to reduce cognitive load. This iteration directly addressed pain points, scaling the app from a simple personal tool to a solution for freelancers and small businesses.
Smart Categorization:
Predicts expense type; users can confirm or adjust.
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OCR Receipt Capture:
Automatically extracts vendor, date, and amount.
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Automated Insights & Summaries:
Generates monthly reports, highlights missing receipts.
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Design decisions informed by research
Based on observed behavioral patterns, the design focused on reducing effort at the point of capture and supporting inconsistent user habits rather than forcing rigid workflows.
Enables immediate capture at the moment of interaction, addressing the tendency for users to delay or forget manual entry.
Quick Capture
Consolidates and organizes digital receipts automatically.
Smart Inbox
Visual overview of expenses, flagged anomalies, and proactive insights.
Monthly Dashboard
Easily send receipts or reports to accounting software.
Export and Share
Impact & Measurable Results
A reduction in the average time spent managing receipts has decreased the monthly administrative burden for freelancers from 5 hours to 30 minutes per month, meaning users can focus on billable work instead of admin — a 90% time savings, allowing satisfied businesspeople to focus on what truly matters.
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Users can now capture receipts on the go without losing data.
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Business owners can manage multi-client expenses digitally with minimal effort.
Key Takeaway for Future Iterations
Through this research, I learned that financial behaviors are highly context-dependent and that even small design interventions can significantly reduce cognitive load during expense tracking.
While automation reduced manual effort, users needed clear confirmation states to trust that the system was working correctly.
This highlighted the importance of transparency in AI-driven experiences. Adding scan confirmations and editable fields helped balance automation with user control. In future designs, I would continue to surface system feedback to reinforce trust without increasing cognitive load
Users consistently prioritized speed over advanced categorization, which reinforced the decision to keep the scanning flow minimal.
In future iterations, I’d explore progressive disclosure for advanced features without slowing the core task
Conducting usability testing early in the process helped identify friction points before visual polish or feature expansion. This prevented unnecessary complexity and allowed design decisions to stay focused on real user needs rather than assumptions.
Moving forward, I would continue prioritizing early validation to reduce rework and keep solutions lean and effective.