When I started at Oscar, the entire company could fit into one conference room. Two years later, it was a highly celebrated innovator (and unicorn) in the health insurance space. As the first designer hired, I helped build our web and mobile experiences from the ground up. Later, I shifted my focus to our brand and marketing. Through design, strategy, and creative direction, I worked to tell the story of Oscar in engaging and powerful ways.


Creative Lead
Brand Creative Strategist


Designed initial website, member app, and internal tools.

Art directed 2015 marketing campaign, including TV, out of home, digital, social and experiential.

Helped hire key creative and marketing roles.

Started Out @ Oscar group for LGBT employees.

ACA 101

The Affordable Care Act (aka “Obamacare”) was the kick in the pants the health insurance industry needed. I won’t bore you with the details, but essentially it created an even playing field for insurance companies to sell to individuals through state and federal websites. It required everyone in America to have insurance coverage (or face a tax penalty) while simultaneously providing substantial subsidies (i.e. discounts) to most people. It also set a relatively high “floor” for what an insurance company could and couldn’t do to make money. No more denying coverage to people who’d been sick before or charging women more than men, to name a few of the more egregious, but common, offenses in the old system.


As a result, an entirely new market was created for health insurance companies to compete on actual quality of service and consumer satisfaction. The founders of Oscar saw that opportunity and, more importantly in this context, convinced me of it’s enormous potential to disrupt and improve a troubled industry at a pivotal turning point.


And true to their word, it did just that.

The beginnings of something big.

My time at Oscar started simply enough. We needed a website. All that existed on HiOscar.com was a list of jobs over a stock photo of the New York skyline at sunset. The end result now feels a little silly; it was a mission statement on our brand color. Nothing revolutionary. But at the time, every decision took on added significance. What did we want this company to be? How did we want to present ourselves? And how did that translate to a web design aesthetic?


I’m more proud of the thinking behind these early projects than the “design” per se, but I’ll present them to show how far we’ve come. All images are for illustrative purposes only.

Marketing Site Hero
Marketing Site Hero HiOscar.com v1
Marketing Site Hero Marketing Site HiOscar.com v1

One early aspect of HiOscar.com that would evolve into one of major selling tools was the “Get a Quote” feature. After much deliberation and exploration, we landed on a “madlib” style UI that has since become quite popular. There are hundreds of factors that go into how much your health insurance will cost, but we boiled it down to as few variables as possible to streamline the process and increase engagement. Even this early version was complex on the back end, but we fought to keep the user experience simple and straightforward.

Get a Quote Madlib Get a Quote “Madlib” HiOscar.com v1
Covering our basics.

Once the marketing site was live, we turned our attention to the member site. At that point, we were only a few months away from actually having members, so the focus was on quick execution. All the basic funcionality of a member app needed to be built from scratch, from log-in to payments to settings to help. Oh and don’t forget about that first of its kind global search we promised. In short, it was a tall order, but it was also one of the most exciting and productive periods of my career.

Care Router
Care Router Member Site v1
App Home
Home iOS App v1
Care Router Search
Care Router Search iOS App v1
Care Router Map
Care Router Map iOS App v1
Doctor on Call
Doctor on Call iOS App v1

My product work extended beyond interactive design to include aspects of packaging design. For example, I worked on the welcome kit that we mailed to all new members. This is a highly regulated and highly personalized piece of collateral, but it’s also a great opportunity to make a strong first impression.


I also designed the first version of our Member ID card. We fought hard to keep this clean and beautiful. Something our members would proudly share instead of the tiny text and logo soup you see with other health insurance companies.

Welcome Kit Welcome Kit Mailed to all Oscar members
Welcome Kit and ID Card Welcome Kit & ID Card
Brand & Expand.

As the “blocking and tackling” was wrapping up, I chose to shift my focus to the brand and marketing of Oscar. I’ve always worked at the intersection of product and marketing, and I saw an opportunity to improve our creative, and help tell the story of Oscar to a growing audience. Every article written about Oscar and every person I talk with about it compliments the brand, which I think is a truly remarkable accomplishment for such a young company. In New York especially, we were able to create a beloved campaign that people remember and genuinely enjoyed.

Oscar Brand

In 2015, I worked with our VP of Marketing to lead an agency search and pitch process. We decided to work with Mother, and quickly got to work producing our 2015 open enrollment campaign. We decided to continue with our popular animated style, and contracted with illustrator Robin Davey to create a new cast of characters. I worked closely with the Mother team to ensure creative consistency and excellence across the campaign.

100,000Out of Home pieces
5TV Spots
7Station dominations
500,000Pieces of collateral
Oscar 2-sheet Ad Oscar 2-sheet Ad Oscar 2-sheet Ad Oscar 2-sheet Ad Oscar 2-sheet Ad Oscar 2-sheet Ad Oscar 2-sheet Ad Oscar 2-sheet Ad Oscar 2-sheet Ad Oscar 2-sheet Ad
2-sheet ads Oscar

After much deliberation, we decided to create a suite of short TV spots in the animated style, each focused around one product feature. The idea that “Health insurance should be a simple as getting sick/hurt” tied everything together.

Chaperone TV Spot
Special Night TV Spot