Simplifying Finances for Freelancers

As someone with experience freelancing, I’ve felt the stress of managing finances—figuring out deductions, categorizing expenses, and dreading tax season. So when I joined Pallo, an all-in-one finance app for freelancers, I knew exactly what our users were facing. My mission was to simplify financial management and make taxes less daunting, with user-centric, empathetic solutions.

‍The challenge 

We conducted user interviews with freelancers to gain insights into their needs, challenges, and workflows. Key pain points quickly surfaced:

• Confusion in categorizing expenses: Freelancers struggled to separate business from personal expenses.
• Uncertainty around deductions: A lack of confidence in identifying write-offs made them hesitant to maximize savings.
• Overwhelmed by tax prep: Using multiple tools and software, tax season became a source of stress.

It was clear that freelancers didn’t just need better tools—they needed a system that felt approachable, empowering, and rewarding.

Prototyping solutions

With these insights, I collaborated with tax experts, product managers, and developers to craft thoughtful solutions.

Simplifying expense categorization

We had an existing feature where users could swipe left or right (like a dating app) to categorize their expenses for personal or business. Swiping left would categorize the transaction as business expense, and swiping right would categorize it as personal. This was a super fun interaction. But users still struggled to know which way to swipe and to understand what they could and couldn't write off.

Smart suggestions

‍To help guide users through this confusing process, we leveraged Plaid’s transaction categorization data. By aligning this data with IRS guidelines, we delivered personalized write-off suggestions for each transaction.

We displayed these suggestions at the bottom of the screen. By default, swiping left or right would categorize that transaction into the suggested category. 

We also added the ability for users to change the category and see what qualified as write-off. Tapping the suggestions would open a drawer, displaying all of the available categories. Each category included a description and examples of qualifying write-offs.

Gamified savings tracker

‍Our aim was to boost user engagement in expense categorization. To achieve this, we introduced a live tracker that dynamically added up business expenses. Now, users instantly saw how each expense impacted their tax return, with motivational boosts as their numbers grew. We enhanced this experience by adding tactile haptic feedback for an engaging, dopamine filled experience.

Reducing tax season stress

To help freelancers navigate the stress of tax season, we built engaging, gamified quizzes into Pallo. These guided quizzes not only simplified the process of entering tax information but also educated users, empowering them to make confident decisions. By the end of the quiz, users had completed a significant portion of their tax preparation, turning a typically daunting task into an approachable and even enjoyable experience.

• Interactive quizzes: Simplified decisions like “standard vs. itemized deductions” into quick, confidence-building questions.
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• Visual dashboards: Clear charts that provide an instant overview of a user's tax situations and potential deductions.
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• Friendly copywriting: Instead of confusing tax terms, we used conversational, reassuring language.

Testing and iterating

I created Figma prototypes and tested them with freelancers, gathering real-world feedback to refine the experience:

• What worked: The savings tracker and suggested categories were highly effective. Users appreciated the confidence boost from suggested write-offs paired with real-world examples. Instantly seeing their write-off value increase made tax preparation feel more rewarding and empowering.
  
  
• What needed tweaking: Early quizzes felt too lengthy and intimidating, so we applied progressive disclosure by breaking them down into smaller, simplified questions instead of overwhelming long forms. This approach reduced cognitive load, helped users feel a sense of progress, and made the interaction more approachable, increasing the likelihood of completion.
  

Results

• Faster categorization: Smart suggestions boosted efficiency and confidence.
• Increased tax savings: Better write-off suggestions led to users maximized deductions, saving an average of 8% more.
• Higher engagement: Gamification encouraged users to spend 23% more time managing finances.
• Less anxiety: Clear visuals and quizzes made taxes less intimidating, transforming dread into empowerment.
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Reflection

‍This project reminded me of the power of empathy and iteration. By staying laser-focused on user needs, we didn’t just improve features—we made a real difference in freelancers’ lives.