Suits + Hoodies: Oscar’s Not-So-Secret Formula

The New York Times calls Oscar, “Silicon Alley’s challenge to the staid business of health insurance.” New York Magazine labels us the company of “the suits and the hoodies.” How is this unique blend of personalities and experiences driving the business? What have the insurance execs learned from the tech whizzes and vice versa? We talked to two of our leaders to find out.

Jeff Cooper has been in the health insurance industry for over 25 years. He loves insurance because, “it serves a social good and it’s incredibly complex and constantly evolving.” His resume reads like a Wall Street analyst’s managed care portfolio: Blue Cross/Blue Shield, CIGNA, physician-owned plans, hospital-owned plans, claims operations, and customer service. As Oscar’s Director of Operations, Jeff oversees claim processing.

Fredrik Nylander began in the startup world in the late 90’s. He describes his passion as, “building things that scale and make a difference.” He has worked at, invested in, and advised some big names, including: Tumblr, Soundcloud, NastyGal, Tictail, Sequoia Capital, and Index Ventures. As Oscar’s Chief Technology Officer, Fredrik brings a startup sensibility to the challenge of solving the health insurance industry’s problems. He’s built a fantastic team in order to figure out how a modern stack can meet regulatory requirements.

When Jeff first heard about Oscar, he was skeptical. “My friend told me this company was looking to change the face of healthcare,” he recalls. “I said, ‘Good luck!’ But he kept calling me, and when I met with the team, I realized this was just crazy enough to work because of the unique power of technology. I viewed it as an opportunity to take what I had learned over the years and do it right this time.”

Fredrik was also excited by the challenge. “It was very clear to me that the American healthcare system is broken. Why not try to disrupt it?” he asks. “But we would not be able to do it without the domain expertise. The complexity of this business is far greater than any other business. Usually as a startup, you can focus on doing one thing better than anybody else, but we have to do a thousand things, and we wouldn’t know what those thousand things were without Jeff and others with his experience.”

Jeff says that it’s this unique partnership that makes Oscar tick. He notes, “In my two decades plus experience with the insurance industry, when you had an idea for a system enhancement what came out as the working product was very different from what you had envisioned. Here, we have such bright and incredible people. They don’t just listen to my ideas; they make them better! Rather than seeing systems projects take 9-18 months, we’re talking 9-18 days.”

Fredrik agrees. “Of the engineers we’ve been able to hire—no one has insurance expertise. They come to us from some of the tech world’s titans: Facebook, Spotify, Tumblr, Google. We’ve been able to attract them because they’re excited to come here and work alongside seasoned experts like Jeff to build solutions for the broken system we call American healthcare.”

by Daniel Liss

…when I met with the team, I realized this was just crazy enough to work because of the unique power of technology. I viewed it as an opportunity to take what I had learned over the years and do it right this time.
Jeff Cooper, Director of Operations

#WeAreOscar: Hi Lamont

Meet @LamontCarolina, our highly passionate & enthusiastic Community Engagement Manager. A Brooklyn native, Lamont has experience working for non-profits, private sector companies and public service. He has worked on a number of high profile political campaigns across the country, including President Obama’s reelection team where he served as Director of Voter Registration for the state of North Carolina and helped to gather more than 340,000 voters! At Oscar, Lamont focuses on finding ways to connect with and give back to the community.

As I started my internship @ Oscar I had no idea what would be involved. I decided to focus my efforts on what I know best: people. I spent the week hopping on phone calls to tell people how amazing Oscar is. In this photo, I was able to sign up a family of 7 baby poms before I realized Oscar doesn’t cover pomeranians. I have a meeting with our CEO tomorrow to talk about pomeranian coverage.

As I started my internship @ Oscar I had no idea what would be involved. I decided to focus my efforts on what I know best: people. I spent the week hopping on phone calls to tell people how amazing Oscar is. In this photo, I was able to sign up a family of 7 baby poms before I realized Oscar doesn’t cover pomeranians. I have a meeting with our CEO tomorrow to talk about pomeranian coverage.

Devil’s in the Details: Visualizing Oscar’s Marketing Engine


Our goal at Oscar is to make insurance simple, intuitive, and human. That experience really starts when people decide to sign up with us.

Providing a high quality consumer experience while coordinating with New York State’s healthcare exchange (which, while not as unstable as the infamous healthcare.gov, has had its difficulties) and navigating an ever-changing web of regulations meant hiring an in-house sales team. In order to get people to our sales center, we devised a marketing strategy that would drive as many of our potential customers there as possible. While we couldn’t control the state exchange itself, we could mediate the experience with our healthcare guides.

But when you try to control the sales process for a product as complicated as health insurance, you’re faced with problems as complex as the system itself. Most companies have some notion of an acquisition ‘funnel’ – a way to think about how you develop relationships with potential customers and eventually convert them into consumers, or in our case, members. It’s a simple idea but can quickly become complicated when you have many points of failure (places where you lose potential customers) and a funnel that blends online and offline processes.

We’ve shared some of our funnel data below (scrubbed, of course) to give you some sense of what we’ve been experiencing in our first few months selling and providing health insurance.

Follow this link to interact with our data visualization.

There are two clear implications: (1) you need to touch a lot of customers to sell a health insurance plan, and (2) when designing a marketing channel, if you have the opportunity to “skip” one of the steps in the funnel, you should. For instance, people who search for Oscar online and go to our site are much harder to sign-up than people who click that same search link on a mobile phone and are instantly connected to our call center.

At the end of the day, understanding the acquisition funnel is about better understanding our customers’ behavior so that we can tailor the experience to fit their needs. We still have a lot to learn, but that’s the goal.

by Gabe Drapos
Visualization by Catherine Moresco

#WeAreOscar: Hi Cleo

Meet Cleo, a sales consultant here at Oscar. As a New York native, Cleo felt compelled to enlist after 9/11. He served as a Counter-Intelligence Special Agent and earned his 2nd degree in Intelligence Operations while deployed in both Iraq and Afghanistan. Although he no longer foils the plans of nefarious terror networks around the globe, Cleo now uses his interpersonal skills and natural communication techniques to guide potential Oscar members through the labyrinth of healthcare. And when he’s not helping folks understand their health insurance options, he stays busy with his podcast and website. Cleo’s positive attitude is as boundless as his smile is contagious.

Fish Plays Pokemon: Internet Phenomenon

Every so often, an Internet phenomenon arises unexpectedly and takes the world by storm. Less often, the architect of such phenomenon happens to be a bright student interning with us for the summer. Meet Catherine Moresco and her Pokemon-playing fighting fish, Grayson Hopper.

So…what is this exactly?
It’s a video stream of my fish playing Pokemon, naturally.

What inspired you?
The short version: it came to me in a dream.
The long version: it was a multi-step process. My friend Patrick and I bought the fish one morning on a whim (we named him Grayson Hopper after Grace Hopper, a pioneer of computer science). But since we both were working full-time tech internships, we didn’t get to see him much, so we bought a webcam and set up a live-stream so we could watch him on our computers at work. Then we just started thinking about what we could do with it—we toyed with the idea of making some sort of interactive game, but the idea for FishPlaysPokemon just struck me in the middle of the night, and it seemed simple and funny enough to work. Patrick and I are part of the awesome HackNY Fellows program, and we built FishPlaysPokemon over the course of about 24 hours for the end-of-summer DemoFest.

How did you build it?
We built a simple motion tracker using python and OpenCV which uses the command-line xdotool utility to send the key press corresponding to Grayson’s location every few frames. It runs on a DigitalOcean droplet.

How did the story get out and gain so much traction so quickly?
Honestly, I’m not quite sure. Virality is strange. I went to bed one night with eight viewers, and woke up the next morning with 22,000 viewers, a subreddit, some really cool fan art, and articles on TechCrunch, BuzzFeed, the Guardian, and BBC. It’s been quite sudden and completely surreal.

What’s next?
We’re going to keep making it better—experimenting with input mapping, cleaning up the aesthetics, and the like. We’re also arranging a better living situation for Grayson, using the donations we’ve received to move him into a bigger, fancier tank. Any donations beyond that will go to the National Fish and Wildlife Foundation.

Beyond Pokemon, though, there are lots of cool things we might do with the stream! A fish-powered random number generator, perhaps. We’re building an API. The sky’s the limit, really!

At the time of writing, Grayson was happy and healthy (despite dark speculation of his untimely death), and enjoying his newfound fame with a staggering 2.1MM views and counting.