Application User Flow Improvements
Progressive Life Insurance
Client:
Level20
(A Progressive Incubator)

Project Overview
Progressive wanted to validate including life insurance as an offering, and the Level20 team (an incubator of Progressive) was tasked with rapid prototyping, testing ideas and gathering learnings to find out if it was viable. At the time of me coming on to the project, they had released an MVP approach to begin collecting data.
​CHALLENGE
The life insurance market was already crowded with options. My project focused on identifying how Progressive could stand out in a field dominated by major players like State Farm and Allstate, as well as boutique companies like Ethos and Ladder. Being part of a large company like Progressive also came with its share of challenges, including navigating red tape and meeting extensive legal requirements.
​OPPORTUNITY
Level20 is an incubator subsidiary of Progressive, meaning we had the freedom of exploration that a start-up has with the financial backing of a major corporation. This allowed us to generate, prioritize, and try ideas quickly using agile development methods. This meant that we were able to explore designs, update content, and update the greater user experience generally within a few weeks based on our iterative learnings.​​
RESULT
I left the project before it was released outside of Ohio (our test market), but the analytics for application completions and sentiment-gathering feedback continued to trend upward with each iteration released to the test market. The internal result of this project was that I was able to help the Level20 team continue to push and test iterative ideas that were pivotal to the success of the life insurance offering, freeing up the lead Level20 designer to focus on building out a complete design system to be used for this new offering.​

How We Worked

Leadership & Strategy

I joined the project as a staff augmentation designer, brought on to support Level20 and lead the exploration of improvements for new applicants and the application process. Reporting to the Lead Designer, I became the second designer on the team. I led the design and research efforts for one of the two development teams, and provided strategic guidance to a new Product Owner. Regular syncs with developers ensured their input shaped our direction and that design and strategy remained practical and implementable.​

Cross-Functional Collaboration

As part of a cross-functional team, I worked with a Product Owner and a team of developers to ensure that we explored and delivered ideas and designs that aligned with the agreed upon strategy. Daily stand-ups, iterative strategy sessions, and presenting my designs to executive leadership ensured a correct course throughout our explorations.

Research & Iteration

Competitor Research

In researching our competition, we discovered a distinct divide between larger companies and boutique brands. Larger companies had the history and reputation to convey trustworthiness, but their application processes often felt impersonal, rigid, and overwhelming. On the other hand, boutique brands came across as more relatable, with simpler and more user-friendly sign-up processes. However, usage reviews revealed a significant drawback: these boutique brands often had lower ratings due to inadequate coverage or poor customer experiences when utilizing the insurance. This is particularly troubling when dealing with the emotional and logistical challenges of a loved one’s passing—an already difficult time that should not be compounded by subpar service.

Diving Into Analytics

Before designing updates, I analyzed data from their MVP. Analytics showed high drop-offs early in the application process. I noticed the MVP failed to set customer expectations for the lengthy application. The team suspected the Social Security field caused drop-offs, but Hotjar recordings showed it was the Driver’s License field instead. We hypothesized that users were starting the process without their Driver’s License on hand, as most people don’t memorize their license number like they do their SSN.​

User Research

To address these issues, I advocated for a Diary Study to better understand user behavior, but the proposal was denied. Instead, Level20 conducted user interviews, which still revealed valuable insights. We learned that the life insurance purchase process often spans multiple phases across different days. People tend to research in small increments, obtain quotes, and then start—and sometimes pause—the application process. This insight emphasized the need for an application experience that was easy to digest, compartmentalized into manageable chunks, and capable of saving progress for later completion.​

Strategy

I suggested reframing our exploration by highlighting the unique nature of life insurance: the purchaser is not the ultimate user. Instead, the user is the loved one left behind to manage the aftermath of the purchaser’s death. Our goal became clear: to create a simple, personal, and trusted process from a well-known organization, providing peace of mind to customers by ensuring their loved ones wouldn’t have to worry in their absence. Progressive already had a strong reputation as a trusted insurance brand, known for quality coverage and reliable claims processes. I emphasized that our focus should be on helping customers navigate a complicated type of insurance with clarity, building trust in their chosen coverage so their loved ones would be well-protected. We began with a handful of strategy exercises, including creating hypothesis to test against and collect data, brainstorming activities to generate ideas regarding our hypotheses, and plotting our ideas on an Effort-Impact Matrix to land on which ideas and features to prioritize as we explored the space.

Design

Given that the workflow could extend up to 10 pages depending on the customer’s needs, we recognized the importance of setting expectations upfront. Starting an insurance application is a time commitment, and users needed to feel confident that their time was well-spent. We introduced an initial landing screen that outlined the process and provided a clear message about what users would need to complete the application efficiently. To further improve the experience, we designed the application pages to feel simple and approachable, leveraging progressive disclosure to reduce the cognitive load on users. This approach minimized the amount of information presented at once, making the process feel less overwhelming. Additionally, we worked to streamline the application by reducing the number of pages and required fields, including the removal of the Driver’s License field.​

Updated Application Experience

This project was part of an incubator initiative to determine whether life insurance could become a viable avenue for the company. By identifying and addressing key pain points in the application process, we reduced drop-off rates and saw higher application completion success. Streamlined workflows, upfront expectation-setting, and progressive disclosure improved the user experience, while save-and-return functionality aligned the process with real customer behavior. 

Success & Expansion

Since leaving the project in July of 2023, life insurance has expanded beyond the pilot state of Ohio and is now available nationwide on their website, reflecting the success of the incubator’s efforts.​

I will also note that since the life insurance offering has been pulled into the Progressive site, it has already changed a lot, but much of the structure seen in this case study can still be felt in the experience.