Building a digital insurance business from the ground up.

Bringing a fresh perspective to a complex industry.

Throughout my career, I've focused on understanding user behavior and building engaging digital products that simplify complex business requirements. I saw an opportunity to apply that same thinking to insurance, making the process of getting a quote feel more intuitive, approachable, and engaging.

I studied acquisition experiences across established insurance carriers, including newer digital-first companies like Lemonade. Its early success reinforced my belief that thoughtful UX could change how customers interact with insurance products.

I also worked closely with our underwriting partner's underwriting, claims, and technical teams to understand the information required to issue policies, the complexities behind coverage, and how their existing systems operated.

Insurance products vary considerably in complexity. Bicycle insurance presented an opportunity to create a more streamlined experience while respecting the underwriting requirements behind it.

The goal wasn't to simplify insurance itself. It was to simplify the customer's experience of buying it.

Getting the fundamentals right before optimizing.

We initially launched with a straightforward, form-based quote experience, prioritizing the core functionality and integration with our underwriting partner's systems.

Working directly with their technical team, we refined and extended existing API capabilities to support the information and quote functionality our bicycle insurance product required.

Rather than optimize the interface while the underlying integrations were still being developed, we focused first on getting a reliable product to market.

Once the platform was operational, we could shift our attention to improving the customer experience using actual behavior and conversion data.

Launch. Learn. Then optimize.

Helping customers get an accurate quote quickly.

We used bicycle industry data to understand popular brands, models, and price points across road, mountain, and e-bikes. Combined with regional information, these insights helped shape the acquisition experience around the information customers were most likely to provide.

I redesigned the quote funnel as a mobile-first, step-by-step experience, replacing traditional forms and dropdowns with intuitive, visual selections.

One deliberate design decision was incorporating recognizable bicycle brand logos directly into the selection process. This made it easier for customers to identify their brand at a glance while creating a sense of familiarity and credibility within the experience.

Customers could quickly identify their bicycle, select its model and value, provide their location and other required information, and receive an accurate quote through our underwriting integration.

Getting a quote was only part of the experience. Giving customers control over their coverage was equally important.

Once a quote was generated, customers could adjust their coverage amount and deductible, with pricing updating instantly. They could explore different combinations and find a balance between coverage and monthly cost without repeating any of the previous steps.

The entire experience was designed around clear progress indicators, tap-friendly interactions, and minimizing unnecessary effort.

Every interaction had a purpose: reduce friction, build confidence, and help customers make informed coverage decisions.

Letting customer behavior guide the design.

Using Google Analytics and event tracking, we monitored customer behavior and drop-off points throughout the quote process.

Those insights helped identify where customers encountered friction, which steps could be consolidated, and where interactions could be simplified.

Across three major iterations, we refined the mobile-first experience to reduce unnecessary steps and make getting a quote as effortless as possible.

The result was an estimated 20% increase in quote completions.

With underwriting and pricing determined by our insurance partner, our focus was on what we could directly influence: helping more customers successfully complete the quote process.

Connecting product experience with customer acquisition.

Shift was built as a digital-first insurance business, with the website serving as both the primary customer acquisition channel and the platform for purchasing and managing coverage.

We reached potential customers through paid search and targeted advertising across cycling websites, forums, and enthusiast communities.

Through research, we discovered that our underwriting partner had an existing relationship with the International Mountain Bicycling Association (IMBA). We built on that opportunity to incorporate membership-based discounts for three cycling organizations: IMBA, USA Cycling, and USA Triathlon.

Rather than requiring customers to find and enter promotional codes, we integrated recognizable organization logos directly into the quote experience. Eligible customers could identify their membership through a simple selection, making the benefit easy to discover and use.

My partner managed campaign targeting, acquisition costs, and media performance, while I developed the supporting creative and focused on optimizing the on-site experience.

The objective was to create a consistent journey from initial interest through quote and purchase, connecting the acquisition strategy with an experience designed to convert.

From an idea to an acquired business.

What began as an opportunity we identified within the cycling market became a functioning digital insurance business, spanning customer acquisition, quoting, purchasing, policy management, and claims.

We combined established underwriting infrastructure with a purpose-built digital experience, using research, collaboration, and continuous optimization to improve how customers purchased bicycle insurance.

Shift was ultimately sold to a larger insurance broker, which incorporated bicycle insurance into its broader product offering for existing customers.

For me, the project reinforced something I've believed throughout my career: understanding the complexity behind a product is what allows you to make the experience feel simple.