A guided end-of-year experience that helps self-employed Lettuce customers review, confirm, and complete their financial data before tax season.
The problem
Lettuce supports freelancers and self-employed individuals in managing taxes, expenses, and deductions throughout the year. As tax season approaches, many face uncertainty about whether their financial data is complete, accurate, and ready for filing. Missing or outdated information leads to errors, delays, unnecessary stress, and missed deductions that cost them money.
The goal was an end-of-year experience that helps users review, confirm, and complete their data without overwhelming them with complexity or tax jargon. It had to support every user state, from fully synced data to entire sections missing, while accounting for deadlines, validation, and error handling.
My role
I was the Lead Product Designer, partnering closely with a Product Manager and front-end and back-end engineering. I owned the end-to-end experience across desktop and mobile, from early structure through final delivery, working in parallel with engineering to meet a tight timeline.
Approach
The project moved from kickoff to production in under one month. Users arrived with very different levels of completeness, and tax deadlines, enrollment changes, and contribution windows varied from person to person.
I designed a guided system that shows users what needs attention, what’s already complete, and what can be skipped. Three sections let users build confidence as they move through the flow, however much their data varies.
| Section | Subsection | Handled as |
|---|---|---|
| Business activity | On-platform income and expenses | Inline |
| Off-platform income and expenses | Custom form | |
| Taxes | Personal details | Inline |
| Off-platform income tax payments | Custom form | |
| Deductions | Retirement contributions | Multi-page flow |
| Health insurance premiums | Multi-page flow | |
| Business use of home and vehicle | Link to existing experience |
I started with wireframes to define information hierarchy, progression logic, and decision points before moving to high fidelity. This aligned engineering early on data dependencies and edge cases, so design and development could move in parallel.
No two users shared the same financial or timeline context. Beyond missing data, the experience had to handle time-based edge cases across the whole year, and sometimes into the next.
Outcome
Three sections, one repeatable pattern, and deadline-aware guidance gave users a clear view of what was done and what still needed attention.
Impact
Reflections
This project reinforced the importance of designing systems that account for time, uncertainty, and incomplete data, especially in financial products where trust is critical. Shipping a complex feature in under a month required decisive prioritization, close cross-functional collaboration, and a strong underlying structure.
The patterns established here created a scalable foundation for future guided workflows in Lettuce and strengthened my approach to designing high-stakes, deadline-driven experiences.
