H&R Block Case Study

GigWorker Onboarding Redesign

"Note: Some details have been generalized to respect confidentiality."

Snapshot

Client: H&R Block

Domain: Tax / Self-Employment & Gig Work

Project: Gig Worker Onboarding & Routing

Role: Senior UX Designer

Timeline: 6 weeks (2 sprints)

Team: PM · Content · Legal/Compliance · Engineering

Outcome: Improved early gig-worker identification and routing by introducing a clearer trigger point and lightweight interstitial education without adding friction to onboarding.

Overview

H&R Block is a leading tax preparation company serving millions of U.S. filers each year through both digital and in-person services. In this project, I worked as a Senior UX Designer on improving the onboarding experience for users with gig-economy income (rideshare, delivery, online sellers, freelancers).

Many gig workers were being funneled into a generic self-employment path, which created confusion, increased drop-off risk, and led to more support needs. The goal was to help users self-identify earlier, route them into the right experience, and introduce lightweight education at the moment it mattered—without adding friction to the flow.

The Problem

Gig workers (rideshare, delivery, sellers, freelancers) were being routed through a generic self-employment flow, leading to confusion, drop-off, and increased support requests. (Ux Design Portfolio)

Why this matters: Gig work is a large and growing segment of the U.S. workforce (McKinsey reports ~36% identifying as independent workers vs ~27% in 2016). (McKinsey & Company)

Goals & success signals

Experience goals

Help users self-identify correctly (even if they don’t use the term “gig worker”)
Route users into the right path earlier
Educate at the right moment without overwhelming

Success signals (what we watched for)

Fewer “wrong path” selections early in onboarding
Higher comprehension of required tax info (forms/deductions)
Smooth progression (no extra steps / no multi-page detours)

My role & responsibilities

Led UX strategy and end-to-end design execution
Designed user-flow logic, trigger-point screens, and employer-specific interstitial content
Partnered with Product + Legal/Compliance + Content to ensure compliant guidance and scalable patterns
Balanced UX improvements with engineering constraints for fast implementation

The Old User Flow

Previously, GigWorker was able to be selected but wasn't specific to users to identify if they were a GigWorker.

Discovery & research

Before diving into design, I explored:

Who our GigWorkers are
User feedback highlighting confusion in the onboarding process
IRS/payment-platform reporting complexity for gig workers (1099-K reporting has had shifting thresholds; current IRS guidance reflects a return to $20,000 and 200 transactions for required 1099-K reporting, with possible lower state thresholds).
Employer-specific tax forms and deductions (e.g., Uber, DoorDash, eBay)
Best practices for interstitial UX to ensure user-friendly, non-intrusive experiences

Here Are Some Insights About GigWorkers

Make up a big part of the Workforce

Make up around 36% of the US workforce compared to 27% of the workforce in 2016

Are lower income, optimistic and driven by necessity

Around 25% of GigWorkers need the extra income, another 25% loves the flexibility

Fall under specified umbrella or category

Contingent Workers, Freelancers, Temp/Seasonal Hires, Side Hustlers & Independent Contractors

Our Improved User Flow

With this improved optimized version, we were able to improve the flow by providing interstitials and page provisions.

Core UX strategy

Identification (Trigger Moment)

Help users recognize their situation with plain-language options (e.g., “delivery apps,” “rideshare,” “selling online”) vs forcing “gig worker” terminology.

Confidence (Education moment)

Give just enough guidance on what to expect (forms, deductions, what to gather) to reduce anxiety and prevent mistakes—without turning onboarding into a reading assignment.

Momentum (Next-step moment)

Use clear, single-action CTAs that keep the flow moving and prevent drop-off.

We focused on 3 core user moments:

However, constraints made things a bit challenging keeping in mind that we must:

1st Constraint

Keep it single-page / lightweight (avoid multi-page detours)

2nd Constraint

Minimal engineering lift (scalable pattern; reusable module)

3rd Constraint

Maintain ADA/WCAG-aware execution (readability, hierarchy, focus states)

4th Constraint

Content must be compliance-safe across employer types and edge cases

Informational Architecture

We were able to gather insights on what would be under the self employed umbrella.

Design Execution

Low → high fidelity wireframes in Figma
Interactive prototypes for trigger/interstitial screens
Dynamic content module for top employers + fallback messaging
Validation through stakeholder reviews + comprehension checks (iterate copy/labels/CTAs)

Solution

A clean, single-page interstitial that routed users into the correct tax path
Employer-specific content (e.g., DoorDash) and general fallback content
Triggered by simple user input based on business activity
Clear CTAs with minimal friction for continued onboarding

GigWorker Final Results

Below is a slideshow that displays the designed trigger points, interstitials and provision for the Gigworker experience.

0. GigWorker Experience Intro

1. Trigger Point Page

7. Rideshare Selection Selected

0. GigWorker Experience Intro

1/8

Results (what improved)

Reduced early-flow confusion by clarifying how users self-identify and where they belong
Improved preparedness by introducing education at the moment it mattered (not before)
Strengthened alignment across UX, Product, and Compliance through structured decision points

Validation (how we knew)

Stakeholder walkthroughs with Product + Legal/Compliance validated wording and risk constraints
Prototype reviews confirmed the interstitial was lightweight enough to avoid drop-off
Final solution adhered to the H&R Block design system and passed dev audit

Key Takeaways

Not all users realize they are “gig workers” — terminology matters
Education doesn’t have to overwhelm if introduced at the right moment
Partnering early with content, product, and legal teams is essential for scalable design

What I’d do next

Next improvements

A/B test trigger-point wording (“delivery apps” vs “gig work”) to reduce misclassification
Track interstitial engagement vs drop-off to confirm education is helping, not slowing
Expand employer coverage with a rules-based content model to scale personalization