Sidewalk (now Butter Insurance) is an insurance technology startup aiming to offer affordable and customer-centric small business insurance to neighborhood entrepreneurs. I partnered with Sidewalk to design and launch a new insurance quote and application experience.

Sidewalk Insurance - Insurance Application - 2022


Lead product designer


Product design, visual design, UX strategy, information architecture

Autodesk (via Supply)  –  Learning platform  –  2019
Lead product designer  –  UX/UI design, visual design, creative direction, UX strategy, information architecture
Client:  Plus  –  Live snapshots –  2021
Role:  Lead product designer  –  Product design, visual design, creative direction, UX strategy, information architecture
Lead product designer
Learning platform – 2019
UX / UI design, visual design, creative direction, UX strategy, information architecture
Image of Sidewalk logo
The founders of Sidewalk recognized that small businesses were having difficulty finding and being approved for affordable insurance. Through extensive customer research and competitive analysis, we uncovered a few key problems with more traditional insurance offerings:
To alleviate these issues, Sidewalk planned to offer transparent small business insurance covering the basics. As a result, they were in need of a quote and application experience to simplify the process.
Design discovery
As an early step in the design process, I led early brainstroms with the cross-functional team of the co-founders and engineers to explore potential solution ideas for the experience. This process ensured that all stakeholders were involved early and highlighted areas of the experience we could focus on.
High-level snapshot of HMWs and early sketches
Image of how might wesImage of sketches
As a next step, I worked to create an accurate user journey to provide the team a foundation to build the experience. Working with the Principal Architect and co-founders, I was able to identify possible constraints and steps in the process that were necessary from a compliance and regulatory perspective.
Image of user flow
Concept iteration
I explored various ideas for interface components, patterns, interactions and layouts. At a baseline, customers needed the ability to move seamlessly through steps, so I explored methods to show actions on a primary level. I also hypothesized that since there could be a lot of steps, we could help set expectations for customers by providing some form of progress tracking.
Image of concepts
Usability testing
To identify what was and wasn't working well, I conducted a round of usability tests of the concepts with prospective customers to gather actionable feedback.
What was working
What wasn't working
Building on the feedback from user research, I focused on iterating on what wasn't working and continued to work with engineering to launch the experience to customers.
In response to the participant feedback about navigation clutter and progress tracking, I made the decision to remove the progress component and hide secondary actions like Contact support and Save & exit in a menu. The total number of steps was smaller than originally intended and these elements proved to have minimal customer value.
Image of Sidewalk screens
Users were looking for transparency around coverage. Focusing on one facet of policies at a time led to further customer understanding about what was covered.
Image of Sidewalk screens
The quote was designed to provide customers with transparency around pricing and the ability to view details before committing. The coverage and pricing breakdowns helped customers understand limits and further policy details.
Image of Sidewalk screens
We successfully launched the experience to a select cohort of potential target customers. As a result, we observed a high conversion rate and positive NPS.