Progessive Life Insurance

A growth-driven UX overhaul for a more accessible life insurance application.

Research, Strategy & Design

​PROJECT OVERVIEW
Client: Level20 (Progressive Insurance)
Project: New Product Release
The Team: 1 UX Designer, 1 Strategist, 1 UX Researcher, 1 Project Manager, 1 Business Analyst, 3 Developers
​Overview:  Progressive’s Level20 team launched an MVP to test the viability of life insurance. I joined shortly after to help improve application completion rates and identify friction in the user journey. Through a series of strategic workshops, user behavior analysis, and rapid iteration, our growth-focused team uncovered opportunities to enhance the experience and drive stronger conversion.
MY ROLE
Role: Senior UX Designer
Responsibilities: Led UX strategy efforts within a growth-driven team. Co-facilitated strategy workshops, led user and behavioral research with analytics support, and delivered actionable improvements to increase application completion. Identified and pitched additional product opportunities aligned with broader growth goals.
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.

Understanding the problem

Starting with high-level data, PowerBI revealed sharp drop-offs during the early pages of the application process, and anecdotal data from surveys showed that the current process was both too lengthy and lacked upfront clarity. Our mission was to dive deeper and uncover the reasons for drop-offs, reduce abandonment, and reframe how users engage with life insurance.

FOCUS AREAS FOR PROJECT:
  • Review current flow and explore updates to reduce abandonment
  • Explore opportunities to educate customers and enhance clarity
  • Look for ways to reduce the length of the application

BONUS: I also took the opportunity to explore the competitive landscape for opportunities of  differentiation from the market, including exploring additional trust building materials.

Evaluating abandonment

Insight
The team suspected the SSN field was causing drop-off on page two, but I wasn’t convinced. I led a review of HotJar recordings and discovered the real issue was the Driver’s License field. Most users didn’t have that number handy and abandoned the process.

Solve
I worked with Legal to confirm it was only required in specific cases. We added logic to show it conditionally, reducing friction for the majority of users.

Learn
This pointed to a bigger gap. Users were starting unprepared. We began exploring ways to better set expectations before the application even begins.

Understanding the users and their journey

I advocated for a diary study to uncover deeper behavioral insights, though the team opted for extended user interviews instead. These revealed that applying for life insurance is rarely a one-and-done task. Users research in phases, revisit quotes, and often pause midway through the application. This led us to design a flow that was easy to scan, broken into digestible sections, and supportive of progress saving.

Research and Planning

GENERATING HYPOTHESIS
I co-led a workshop to surface potential friction points and draft hypotheses with assumed fixes. I then mapped these to research opportunities, validating the strongest ideas and folding them into our prioritization framework.
EFFORT-IMPACT MATRIX
I led the team through an effort-impact matrix to prioritize our updates. We aligned on what would drive the most value with the least lift, helping us build a clear roadmap and move faster on testing and iteration.

Simplifying and updating the application flow

Over the course of 10 months, a combination of strategy workshops, behavioral data, and in-depth interviews led to a number of impactful updates:

  • Reduced Pages: We cut the application flow from a minimum of 26 to minimum of 19 pages, streamlining the process and reducing user fatigue during an already sensitive, high-effort task.
  • Save & Retrieve Functionality: Based on journey insights, we added the ability for users to pause and return later, better matching real-world behaviors and reducing abandonment.
  • Progressive Disclosure: To prevent overwhelm, we introduced drawer-style UI patterns that revealed only the most essential fields first, keeping screens focused and clean.
  • Progress Bar: A small but critical addition, the progress bar helped users orient themselves and commit to finishing.
  • ​Overview Page: We added a start screen that previewed required documents and outlined the overall process, setting clear expectations and helping returning users pick up where they left off.

Each of these updates stemmed directly from insights we uncovered through analytics, Hotjar data, and customer interviews, and they collectively created a far more thoughtful and user-aligned experience.

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 friction 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 my time on the project ended in July 2023, Progressive has expanded the life insurance offering beyond its original pilot in Ohio, rolling it out nationwide. This is a clear signal that the incubator met its goals. While the experience has evolved since then, many of the structural elements and design principles introduced during my involvement remain visible in the current product.

✨ Additional Bonus Work ✨

During my time at Progressive, I was predominantly over the growth-focused team from a design and strategy lens, helping to make incremental and meaningful impact. But in addition to that work, I was also given free rein to evaluate the current flow and explore other, future-facing opportunities for the business.

Competitive landscape

I evaluated both big and small competitors from a visual perspective, usability perspective, and read through reviews, to figure out what each was doing successfully (or failed at) in order to learn where and how Progressive could differentiate themselves. Here were some key findings:
  • Big competitors (like Allstate and State Farm) were generally seen as higher priced, more difficult to complete the process, but also more likely to pay out in the event of the death of a loved one.
  • Smaller competitors (like Ethos and Ladder) had amazing reviews in terms of sign up process, with clients mentioning the low prices and ease of use, but other reviews mentioned that it was difficult to get them to actually pay out during the time of need.

The Proposals

General confusion about life insurance

Reviewing a number of different websites, as well as looking through Progressive's own user research, the sentiment was share by MOST customers: life insurance is confusing, expensive, and people aren't really sure why they need it.

It was during this evaluation of all of these sentiments that I realized something. Purchasers of a life insurance plan are the users. The family left behind are the users. We are trying to get someone to understand why they need something they will never use. And most competitors are trying to help them understand via an FAQs page. There couldn't be a less personal touch to an event and service offered for an extremely personal reason.

"Purchasers of a life insurance plan aren't the users.
The family left behind are the users."

Creating a personalized customer story

Life insurance has always been explained through short snippets on a marketing page, or through a boring FAQ, and yet people still don't understand. Weird, huh?

THE IDEA
My idea was to place the user into a story that they would help build. This story would include their family members, their stage of life, how much they made, etc. In this story, they would die... An explanation would help them understand the costs of everything there family is left with. This would help users understand the the importance of life insurance AND understand why a recommendation can feel high.

Deliver a physical keepsake to beneficiaries

The purchaser of a life insurance plan isn't the user. The family left behind is the one that has to use it and deal with the aftermath. Reviews provided horror stories of users not knowing who to contact, what to expect around required information, or flat out being refused the insurance payment their deceased relative had purchased.

THE IDEA
Create a simple, physical keepsake (or a pdf) that can be mailed to beneficiaries that includes easy to follow instructions in the event of the purchaser's passing. It would ideally remove any complexity or worry regarding life insurance when a family is already hurting and in no place to deal with insurance bureaucracy.

The Outcome

The outcome is a bit anti-climactic. Both ideas were presented to leadership along with supporting research, and while the ideas were considered good ideas, they were placed on the back-burner due to a focus on incremental growth and improving the content currently available. We will see if either of these ideas ever come to life.

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