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PORTFOLIO > CASE STUDY #2

Designing a premium subscription upselll

Boosting recurring subscription revenue with a timely call to action

Context

Problem

Found, a business banking platform for self-employed professionals, needed to transform its tax filing integration into a strategic growth opportunity. The goal was clear but complex: design an intuitive upsell experience that would encourage annual subscriptions while providing value to users across different subscription tiers.

Approach

Instead of treating this as a simple transactional upgrade, we approached the challenge as a holistic user experience design problem. Our mission was to create a seamless, user-centered journey that felt less like a sales pitch and more like a helpful financial solution.

I led content design and strategy, focusing on clear and actionable messaging to guide customers in their decision-making. Collaborating closely with a product designer, engineer, and product manager, I helped define flows, worked within technical constraints, and ensured compliance with UDAAP regulations. I also iterated on content based on stakeholder feedback and performance data.

Goal

Found set a goal of acquiring 150 new annual Found Plus subscribers during tax season, leveraging the filing integration to boost engagement and retention. Customers using the integration were expected to maintain higher balances, deposits, and card spending—driven by awareness of automated write-off benefits and the balance required for free filing.

Key outcomes

  • Added 180 new Found Plus annual subscribers

  • Generated $20K in direct subscription revenue

  • Tripled TurboTax revenue

  • Increased user engagement among tax filers

  • 39% of tax filers became annual subscribers

Design process

Understanding user needs and constraints

An earlier MVP limited to tax extensions allowed customers to file taxes without a subscription. While the MVP wasn’t gated, the new version introduced paid access, which required a significant redesign to accommodate pricing and subscription options.

I reviewed the MVP alongside the product designer and project manager to identify opportunities and constraints. The goal was to adapt existing flows as much as possible to minimize engineering’s effort.

Mapping user flows

By mapping flows for annual, monthly, and trial subscribers, we identified key decision-making patterns and potential friction points. For example, we discovered that insufficient funds were a barrier for annual plan sign-ups. To address this, I created a flow prompting customers to add funds, followed by a reminder email once the funds cleared, guiding them back to the tax filing process.

Designing entry screens

We created a two-step entry process to guide users through their options clearly and simply. The first step focused on the benefits of Column Tax with straightforward messaging to avoid overwhelming users. The second step presented two choices: upgrade to Found Plus for free tax filing or pay a one-time $79 fee.

I framed the messaging to give users clear, positive options while prioritizing clarity. For example, we used parallel phrasing like "File for free" and avoided negative language, such as “Continue without upgrading.” Working collaboratively in Figma, I refined the content with the designer, ensuring a balance between clarity, simplicity, and compliance.

We tested various design options, including lists and radio buttons. After gathering feedback from the design team and refining the content, we chose radio buttons for their simplicity, minimizing cognitive load by avoiding detailed pricing on the first screen.

Throughout this process, I worked closely with the Chief Compliance Officer to ensure the UX flow and content met UDAAP regulatory standards.

Optimization

Adapting for S Corps

When Found expanded to support S Corps—a customer segment not covered by the Column Tax integration—it initially seemed like a roadblock. Instead, we pivoted quickly, introducing a TurboTax option to fill the gap and broaden our value proposition.

I proposed repurposing a TurboTax discount code already in the app and updated the design to feature it prominently for S Corps, aligning the CTA with their tax-filing goals. Midway through tax season, strong conversions among S Corps led us to extend this option to sole proprietors as well.

To ensure all users had relevant resources, I revised the in-app tax guide to include both Column Tax and TurboTax options with clear, actionable links. This approach resolved the challenge while improving usability and engagement.

Outcome

Found’s tax filing integration and the elevation of the TurboTax offer exceeded expectations, driving meaningful growth for Found:

  • Subscriber growth: Column Tax added 180 new Found Plus annual subscribers, generating $20K in revenue.

  • Revenue increase: TurboTax revenue tripled year-over-year, reaching $42K in 2024 compared to $13K in 2023.

  • Engagement boost: Tax filers had significantly higher balances, deposits, and spending. Among tax filers, 39% were Found Plus annual subscribers, far exceeding the average attach rate.

This project reinforced the importance of deeply understanding the product as a content designer. It reminded me of the value of zooming out when revisiting MVPs to understand how they fit into the broader product and its ongoing evolution. It also taught me the importance of flexibility in design, especially when addressing unexpected gaps. We were able to pivot quickly because of the high level of communication and collaboration within our team.

Beyond the immediate metrics, we created an upsell experience that:

  • Respected user agency

  • Provided clear, actionable choices

  • Aligned business goals with user needs

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