Ivan Wicksteed, Chief Marketing Officer of Oscar Health
Ivan Wicksteed
Chief Marketing Officer Oscar Health logo

Old Navy and Cole Haan Former CMO Ivan Wicksteed Reinventing Health Care With Oscar Health

So why would the former CMO of Old Navy and Cole Haan with an earlier role leading International Marketing for Converse decide to become the CMO of Challenger Brand, Oscar Health? Find out from Ivan Wicksteed himself in this deep dive into modernizing the customer experience in one of the most complicated categories of all time, health care.  As Ivan takes us through his journey with Oscar, he shares some incredible lessons that he learned from his prior roles that continue to influence his direction on a daily basis. And don’t miss his perspective on two pitfalls that often cause startups to fail.

Tell us about your background and why you chose to join Oscar.

I’ve always been attracted to brands that challenge the status quo and have led marketing teams at a number of them. For example, Converse was in many ways the ultimate challenger brand for years, embodying the counter-cultural spirit of the times. Old Navy is an establishment Goliath, but we were able to keep the brand feeling irreverent and mischievous during my time there, largely by working with left-of-center talent. Even at Cole Haan, which was once a very traditional brown shoe company, we had a lot of fun incorporating modern technology into the brand DNA, courtesy of Nike's running shoe expertise.

"...we are challenging the status quo in a system that is deeply broken."

What’s different and exciting about Oscar is that we are challenging the status quo in a system that is deeply broken. The inability to pay for health care costs is the leading cause of personal bankruptcies in this country. We pay significantly more than any other nation for our health in the United States, but our health standards and outcomes are actually declining in a few important areas. At best, health care is confusing and opaque for consumers. At worst, it is financially ruinous.

How is Oscar Health challenging the industry?

Health insurance is an extremely entrenched industry that operates inefficiently and sometimes ineffectively.  Oscar is trying to fix this by putting member service at the center of what we do and making health care easier to navigate. We recognize the need to define ourselves against the establishment. When Oscar launched seven years ago, we were the first new health insurance company to file for a license in New York in decades.

Oscar made an early bet on virtual care, fully integrating free, 24/7 telemedicine access for all members. That means if you get sick, you can call a doctor at any time. Today, many other companies do this, but none invested as early or as significantly as Oscar. Oscar is making a long-term bet on the future of virtual care, which is a transformational idea.

Oscar Health mobile app
Oscar Health mobile app puts patients in touch with a dedicated concierge team 24/7.

Most insurance companies work from a transactional model, which essentially makes them large billing companies. In contrast, Oscar has always operated on an engagement model. Our telemedicine engagement – which is 5x higher than the industry average – is evidence of that. This engagement enables us to understand our customers better and provide more effective coverage for them.

What shifts are happening in marketing that most excite you and how is Oscar responding through innovation?

"The future of marketing is 'mass personalization.'"

The rapid shift toward personalization is the single most compelling development in the marketing industry. The days of blanketing messaging across large groups of people are dying along with traditional media. The future of marketing is “mass personalization.” The companies who will win at this game are those who own the customer data and so are able to identify and target niche groups en masse.

Oscar has spent the last few years building our technology stack from the ground up, so we have a unique picture of how members engage with us, what their treatment history is, and what they care most about. In the future, health care will become increasingly about predictive care rather than reactive care, which takes this conversation to a whole new level.

There is an insane amount of work happening every day here to improve the digital experience – much of which leans heavily on machine learning. Algorithms can do a lot to improve the efficiency of the system, like reducing the time it takes Oscar to pay claims to 6 days, as opposed to 2-3 weeks, which is the industry norm.

That's not to say there is no need for humans in the equation. I just got back from a trip to our office in Tempe, Arizona, where our Concierge Team is headquartered. The team, which is made up of care guides and registered nurses, helps our members navigate their health care by supporting them with tasks such as finding the right doctor or managing chronic disease. The team is absolutely devoted to making the health care industry less opaque for our members. Notably, 74% of members said they trust Oscar to give advice on how and where to get the care they need, with 30% citing our Concierge Team as the number one reason they trust Oscar.

What lessons did you learn early on that have stuck with you? 

"Changing course was going to be expensive, and painful. But it was the right thing to do."

In my early days at Old Navy, I learned a very important lesson about having the humility to understand when you're wrong, and the tenacity to change course when needed. In my first few months there, we were heading in a direction, strategically, that was just wrong. We were not embracing price in the right way as a key differentiator for the brand. Changing course was going to be expensive, and painful. But it was the right thing to do. Three years later, we had added almost $1 billion to the company’s revenue. It was the right call.

What mistakes have you seen entrepreneurs and startups make?

It’s cliche to say that every successful entrepreneur has to have failed at least once, but I think it’s true. My biggest lessons have come from my mistakes, and I’ve probably made every mistake at some point. The two biggest mistakes I’ve seen startups make are failing to bring a minimum viable product to market quickly enough and then failing to secure enough funding to give it a proper runway.

What one trait is most critical to leading a Challenger Brand?

"Challenger brands exist to create change. They derive their power from the broken industries in which they operate."

Never forgetting the mission. Challenger brands exist to create change. They derive their power from the broken industries in which they operate. When Virgin launched their first transatlantic flights, they put themselves on the map by challenging the establishment, which at that time was British Airways. Apple, Lyft, Dollar Shave Club, and Casper all do the same in their respective industries. When you are a challenger brand you have a responsibility to speak differently, look differently, and act differently. You can’t ensure this happens without keeping the company’s mission at the front of your mind.


Check out the full Challengers series for more brand leaders challenging the status quo.