Sole product design lead / Oscar Health / Mar - May 2020

Context

Oscar was well-known for its direct-to-consumer health insurance plans but wanted to expand into small business insurance.

However, most brokers were stuck managing quotes and enrollments with spreadsheets, email threads, and manual forms. The experience was slow, error-prone, and a poor reflection of Oscar’s brand. 

Problem

Brokers had no streamlined way to quote, compare, or enroll clients. They were working around the system, relying on third-party tools and offline methods that led to delays, mistakes, and frustration. For Oscar, this meant slow adoption and missed opportunities in a high-value segment.

Costly for brokers
Manual data entry and communication are time-consuming, error-prone, and inefficient, leading to significant wasted hours.

Inefficient for clients
The quoting process is slow and unclear, requiring frequent back-and-forth communication, causing delays and frustration.

Difficult to track and scale
Manual workflows lack visibility and scalability, increasing errors and making it hard to manage multiple clients or ensure accuracy.

Solution

We needed to build the entire quoting and enrollment experience from scratch and do it in a way that matched how brokers actually worked, not how insurance paperwork traditionally functioned.

We developed a fully digital platform that automates critical steps while enhancing the overall experience for brokers and business administrators. 

Census-first quoting to reduce friction and improve accuracy.

Brokers needed a faster way to quote without repetitive data entry. We redesigned the flow to move basic employee census data (age, location, and tier) to the start of the process, allowing brokers to receive accurate plan recommendations early. Names could be added later, aligning with real-world broker workflows and reducing system-hopping. This streamlined experience minimized errors and helped brokers quote confidently and efficiently.

Smarter plan comparison that saves time.

Brokers were wasting hours compiling plan details into spreadsheets and PDFs. We replaced that with a side-by-side comparison tool that lets brokers filter by key criteria like metal tier, deductible, and drug coverage and compare up to 5 plans at once. Built from broker feedback, it reflects how they actually sell: focusing on a few tailored options. With branded PDF exports and shareable links, brokers can now present polished quotes quickly and clearly to clients.

A centralized dashboard for ongoing management.

After narrowing down plans, brokers can either enroll immediately or save quotes to revisit later. We built a centralized dashboard where they can track quote versions, manage enrollments, and make real-time updates all from one place. It gives brokers full flexibility and visibility across every group they manage, streamlining a once-scattered workflow into a single, efficient hub.

Guided plan selection to reduce complexity.

During enrollment, brokers typically narrow down to just 2–3 plans. To align with this behavior, we limited plan selection to 1 primary and 2 secondary options simplifying decision-making, preventing overwhelm, and helping both expert and novice brokers focus on the most relevant choices for their clients.

The quoting-to-enrollment journey can span weeks and vary widely by client. 

Brokers handle a wide variety of clients, each with their own unique needs and requirements. We learned that brokers often deal with complex scenarios in the flow like changing contribution amounts, varying plan types, and specific client needs that affect enrollment. To cater to different use cases and also minimize overwhelming fields presented all at once, I designed the flow with progressive disclosure.

Process

We learned that brokers’ workflows vary depending on their experience level, client size, and the specific needs of the clients.

We began by deeply understanding broker and business administrator's workflows and how each broker interacts with the quoting and enrollment process to make sure that we build a system that's inline with their needs. This helped us understand the challenges brokers faced at each step from gathering census data to comparing plans and enrolling employees. We learned that brokers’ workflows vary and the specific needs of the clients they work with so we had to distill down and map out what the common steps were and which were edge cases. 

Results

This wasn’t just digitizing forms. It was designing for real broker behavior. By reducing friction and respecting how brokers worked, we gave them a reason to stay in Oscar’s ecosystem.

We saw faster time-to-enrollment, an increase in broker-led self-serve enrollments, and this became an entry to Oscar's SMB insurance, laying the groundwork for future group product expansion.