The Stride App: Unlocking saving opportunities for the independent worker beyond a mileage tracker app.

Stride’s mission is to make independent work easier by helping workers manage taxes, finances, and their benefits in one place. While our free mobile app attracts thousands of independent workers each month—primarily for its mileage tracking feature to save on taxes—most users are unaware of other valuable features like our deduction tracker and insurance options. In addition, the app’s core functionality was difficult to find, and the experience didn’t clearly communicate its full value. As a result, user engagement and retention suffered, limiting our ability to earn user trust and monetize them through the purchase of benefits.

From the user’s perspective, many new independent workers aren’t sure what steps they should take to maximize their earnings. They know tracking mileage is important for taxes, which brings them to Stride, but they often feel uncertain or anxious about what else they should be doing. Additionally, users who come to the app to track their mileage can feel overwhelmed or frustrated by prominent insurance offers and ads, which disrupt their workflow and diminish trust in the app.

Through several customer interviews, I learned that new independent workers download Stride mainly for the free mileage tracker, but are unaware of other ways to maximize their earnings or manage their taxes. Several of our customers see Stride as a simple mileage tracker tool, not a holistic platform for financial management and benefits.

To address this, we focused on delivering immediate value with an intuitive, best-in-class mileage tracker experience. Our hypothesis: if users quickly see tax savings as soon as they finish their first drive, they’ll be more likely to explore additional features like expense trackers and benefits, leading to higher engagement and retention.

To achieve this, we explored several concepts—including guided tours, checklists, and a mileage tracker-first approach—all designed to educate users with practical, bite-sized tips and gradually introduce them to Stride’s full range of money-saving features. Below are a few of the concepts I explored with my team.

designed an experience that both acknowledges users’ primary goal—tracking miles to save on taxes—and introduces them to other key money-saving actions with equal visibility. Our solution had two main components:

1. Onboarding Education: We revamped the onboarding flow to clearly outline all the essential actions independent workers can take to save money, not just mileage tracking. This was importnat because workers who are new on the field are not aware of all the things they need to do to save on their taxes

2. A new app Dashboard that introduces all the tax-saving opportunities in context: The new dashboard presents all the core functionality users would need to save money on their taxes—as distinct, actionable opportunities within the app, making it easy for users to discover and engage with each one.

• The stats widget: Tracks all the tax savings, which gets updated after a user completes a core-action
• The Stride Dash: Quick menu to the 4 core-actions that lead to tax savings
• An education moment: Provide access to quick/stackable content that increases financial literacy
• See the Stride app feature set for details.

This approach ensured that while users could immediately fulfill their initial need, they were also guided toward a broader set of financial tools to maximize their earnings as independent workers.

Our redesigned onboarding and feature discovery Dashboard had a measurable impact on user engagement and retention. By guiding new users to immediate tax savings and introducing them to additional money-saving features, we increased 1-day retention from ~33% to ~36% and 7-day retention from ~22.5% to ~24%.

 These improvements represent hundreds more users each month returning to Stride, exploring more features, and building trust in the platform. Early data also shows increased engagement with expense tracking and benefits exploration, validating our hypothesis that delivering quick wins up front leads to deeper, longer-term relationships.

Most importantly, we’re helping more independent workers feel confident in managing their finances and maximizing their earnings—directly supporting Stride’s mission to make independent work easier and more rewarding.