The Communicator Now Running Oscar Health's Marketing

Most people never read a single word their health insurer sends them. They glance at the envelope, feel a small dread, and file it under later. For anyone whose job is to make a health company worth paying attention to, that reflex is the wall to climb. Kristen Prestano has spent a whole career studying why that wall exists, and now, as Chief Marketing Officer of Oscar Health, she is the one being asked to take it down.

Her promotion is the kind of move that looks small in a press release and says a lot underneath it. Oscar Health, the New York technology company that has been trying to make health insurance behave more like a consumer product, took the person who had been running its communications and handed her the marketing keys as well. The two jobs became one job. For a company built on the idea that the story and the sale should sound the same, that is not a footnote. It is a statement of intent.

A career built on explaining hard things

Prestano did not arrive at marketing through the usual door of ad campaigns and slogans. She came up through communications, which is a quieter and in some ways harder discipline. Communications is the work of taking something complicated, often something a company would rather not explain at all, and saying it plainly enough that a busy person can understand it and still trust you afterward. She has been doing that at scale for years.

She studied communication at Fairfield University, then went into financial public relations at Prosek Partners, a New York firm known for handling clients in banking and professional services. That is a demanding training ground. You learn to write for skeptical audiences, to move fast when a story breaks, and to hold a message steady when the numbers are moving. It is where a lot of good corporate communicators are forged, and it gave her the habit of clarity under pressure.

From financial PR she crossed into healthcare, which is where the stakes and the scale both jumped. At Cigna she took a senior role in business and executive communications, leading messaging for the company's US business lines, customer segments, and corporate strategy. That put her in the middle of one of the biggest transactions the industry had seen in years.

The Cigna-Express Scripts merger came in at roughly $67 billion, and mergers of that size are as much a communications problem as a financial one. Employees get nervous, customers wonder what changes, regulators watch every word, and the market reads the tone as closely as the terms. Prestano helped steer the message through the deal and the integration that followed, which is the unglamorous part where a lot of mergers quietly go wrong.

Integration is where the real communications test lives. Two companies with two vocabularies, two sets of habits, and two nervous workforces have to start sounding like one. Somebody has to decide what the combined thing is called, what it promises, and how it explains itself to the people who depend on it. Get that wrong and the deal that looked brilliant on a spreadsheet stalls in the hallway. Work like that rarely shows up in a headline, but it is where a communicator either proves their worth or does not.

From a giant to a challenger

Her next step kept the scale but sharpened the focus. She became Managing Director and Head of Communications for Evernorth Health Services, the health-services arm inside The Cigna Group, a business reported in the range of $112 billion. There she owned communications across the enterprise, including executive communications for the unit's leadership and the relationships with national and trade press that decide how a company like that is understood from the outside.

Running communications for a company that large teaches a particular skill: how to make something enormous feel legible. A member, an employer, a reporter, and an investor all need a version of the same truth in a language each can use. That is the muscle she carried into Oscar in 2023, first as Chief Communications Officer, where her brief already reached past press releases into brand, design, and creative for Oscar's family of companies.

Because she already held brand and creative before she held the marketing title, the voice she now owns was partly hers to begin with. The promotion did not hand her a new instrument so much as let her play the one she had been tuning. That continuity is easy to miss and probably the point of the whole decision.

Why clear beats clever here

Oscar has always positioned itself against the grey, form-heavy image of traditional insurance. It leans on a member-friendly app, a concierge-style care team, and a brand that tries to sound like a person rather than a policy document. Reaching Spanish-speaking members through a dedicated effort has been part of that too. All of it depends on communication that respects the reader, which is exactly the discipline Prestano spent two decades practicing.

The challenge is real and it does not yield to spending. You cannot discount your way into someone's attention when the product is coverage they hope they never have to use. You have to earn the attention honestly, and you have to keep it by being understood. That is a communications problem wearing a marketing badge, which may be the clearest reason the two roles ended up in the same pair of hands.

It helps that the raw material is human. Behind every plan choice there is a person weighing a monthly cost against a what-if, a parent picking coverage for a family, a small employer trying to do right by a handful of workers without a benefits department to lean on. Marketing that talks down to those people, or hides behind fine print, tends to lose them. Marketing that treats them as adults, tells them the price, and shows them the doors that are open has a chance. The tone is not decoration. It is most of the product experience before anyone signs up.

There is a broader shift her promotion sits on top of. For a long time, companies treated marketing and communications as separate crafts with separate instincts, one loud and one careful. Customers never saw it that way. To them, the ad, the press statement, and the message in the app are all just the company talking. The organizations that come across as trustworthy are the ones where all of it sounds like the same honest voice, and building that single voice is precisely what a communications leader is trained to do.

It also says something about how she has worked. Communications is the function that gets trimmed first in a hard quarter and thanked last at the all-hands. Building a long career in it, and then being handed a larger mandate rather than being replaced by someone flashier, is its own quiet endorsement. The trusted path is slower, and then one day it compounds into chief of the whole story.

The test ahead

Now the work gets measured in public. Oscar is a listed company with roughly $11.7 billion in annual revenue and a large membership across individual, family, and small-group plans. Marketing there is not a mood, it is a line that connects to growth, and everyone can see the numbers. Prestano steps up alongside other leadership moves at the company, including a new growth-focused role, which suggests Oscar is arranging its top team around getting bigger and being understood while it does.

What she is really being asked to prove is an old, stubborn idea: that plain, respectful communication can do the heavy lifting that clever campaigns usually get credit for. If a health insurer can become something people actually read, and maybe even something they recommend, it will be because someone insisted on clarity when the easier move was noise. She has spent a career making that argument for other people's companies. Now she gets to make it for one that put her name on the door.

It is a good problem, and a hard one, and she is unusually well suited to it. The wall is still there. The person now assigned to take it down has been reading the blueprints for twenty years.