Stride Health
Responsive redesign to help independent workers get insured
Stride makes health insurance easier for independent workers — rideshare drivers, Etsy sellers, anyone without coverage through an employer. As lead designer on the marketplace team, I redesigned the application within strict government requirements, adding a results page that shows eligibility and next steps at a glance, refined over two rounds of testing.
- Role
- Lead designer, marketplace team
- Worked with
- Member experience team, product manager, engineers
- Platform
- Responsive web
- Tools
- Sketch, InVision, Zeplin, Jira, G Suite, Zoom

The goal
Growth in membership: improve the application process and increase the number of people signing up for insurance.
Reviewing the current design
I started by meeting the member experience team to understand past issues and the pain points people ran into while filling out the form.
Who are Stride's users?
People who work independently — Uber drivers, artisans selling their work on Etsy, or anyone who doesn't get insurance through an employer.
Understanding the flow
A challenging and essential part of this was working with government entities. While making the experience better, I still had to fulfill strict government requirements.
Working with the team
This is my favorite and most rewarding part of being a designer: collaborating with engineers, product managers and other stakeholders. It pushes the best designs forward, and helps me grow too. As the primary designer, I worked closely with engineers to give them the bigger picture.
Results page and evolution of the design
A key addition was a results overview page, so people could see their eligibility and next steps at a glance. Two rounds of testing — one internal, one external, run with the product manager — shaped each iteration.

Early iteration
- ✓Eligibility was clear
- ✗Essential deadlines weren't shown

Mid-process iteration
- ✓Easy to read and understand
- ✗People still didn't understand their action items
- ✗The steps at the beginning went unnoticed

Final iteration
- ✓Easier to see important action items and deadlines
- ✓More specific exceptions for each member
- ✓Shows the details required by government
- ✓Names of eligible members take less space, so the page is quicker to scan
Learnings
- Work quickly, and accept that not every design has the capacity to come to life.
- Push back on some experiences, and stand firm on the ones that matter most.