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ISSUE 04
Enterprise SaaS UI

Shipping a critical tax workflow in ~3 months

Redesigning a financial workflow through a guided export that meets IRS standards

Business Challenge

What was broken, why it needed to be fixed & who benefits once we do

Overview

The IRS introduced new filing requirements for the 2024 tax season that significantly increased the need for electronic tax filing. As the sole designer on a tight timeline, I reimagined the tax export experience from end to end, transforming a confusing legacy process into a guided, step-by-step workflow.

My Role
  • Sole product designer
  • Information architecture & interaction design
  • Cross-functional collaboration from concept to launch
The Crew
  • Garrett S.·Business Analyst
Timeline
Dec ‘23 – Feb ‘24
Tools
Figma

Solution

A shared workflow designed for everyday coordination

Export 1099 wizard, Summary step reviewing transmitter and payer information before export Export 1099 wizard, Transmitter Information step with company and contact fields Export 1099 wizard, Getting Started screen listing what's needed before you begin

Solution: A guided, step-by-step export wizard that walks property managers through the 1099 filing.

Impact: Shipped redesign in ~3 months Introduced guided workflows Improved user confidence

What I Owned

I owned the end-to-end design of the 1099 export experience, transforming a complex, single-page process into a guided sequence of focused steps.

The 1099 export wizard's Transmitter Information step, with a numbered progress sidebar for each step of the export

How I Collaborated

Partnered closely with Garrett to validate the workflow and ensure the final experience accurately reflected tax requirements.

Chat message from Garrett with an annotated screenshot of the 1099 export wizard's Corrections step, requesting a field-label change

Pain Points

How we identified the biggest sources of friction across users

Pain points across tenants, technicians, and property managers
Constraint 01

IRS Filing Deadline

A hard external deadline required a rapid turnaround

Constraint 02

Errors Had High Stakes

Incorrect tax filings could have big consequences later on

Constraint 03

Meeting New Requirements

The new design should be integrated, not an add-on

Research

Insights that informed our design decisions

What We Did

We used common sense! Due to the quick turnaround for this project we didn't have time to do any formal research. This is where designing for systems comes in, as we implemented the Walkthrough Wizard that I originally introduced as an onboarding flow in the previous Maintenance scheduling project.

Utilized existing components which saved precious time creating a custom solution

Hand-annotated screenshot of the Corrections step in the 1099 export wizard, flagging UX issues

What We Cut

Correction files

Correction-file generation was separated into its own project rather than adding another workflow to the 1099 redesign. This kept the scope focused on improving the core export experience while allowing the new correction functionality to be addressed separately.

Design

Exploring iterations and tradeoffs to reach a user centric solution

Old 1099 Export screen — flat form with Transmitter Info, Vendors and Owners, and Options all on one page

Before: 1 scrolling page with no guidance.

After: One set of decisions per screen, built-in validation along the way, and a final summary to review before anything gets submitted.

Impact

How the business and its users benefitted after launch

My Influence

By designing for systems and not individual features, I was able to create scalable patterns that reduced development time and increased time to market

Payer Information step, annotated to highlight the clear, numbered wizard steps
Create Renewal Offers screen, annotated to show the same stepper pattern reused in a different workflow

Shipped redesign in ~3 months

Designed and launched the new experience in under 3 months to support customers ahead of the IRS filing deadline.

Introduced guided workflows

Established a reusable pattern for breaking complex product experiences into focused, sequential steps.

Improved user confidence

Replaced a complex single-page workflow with guided steps that reduced cognitive load and made progress and requirements visible.

Reflections

Hindsight is 20/20

What I Learned

  • Users appreciate guidance.
    By breaking the tax process into focused steps, I could reduce the amount users had to reason about at any one time while still giving them the control they needed to complete the filing.
  • Confidence is an interaction problem, not just a content problem.
    Making requirements, progress, and next steps visible from the beginning became just as important as simplifying the interface itself.

What I'd Do Differently

To be honest, there isn't much of anything I'd change here, besides maybe having my devs stylize it closer to my original design! :)

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