Our New and Improved Open Enrollment Onboarding Experience

Sara Wajnberg
Oscar Tech
Published in
7 min readOct 23, 2018

Co-authored by Sara Wajnberg, SVP Product, and Duncan Greenberg, Director of Product

Fall is here and with it comes Open Enrollment, the high-adrenaline sales season in which Oscar will enroll the bulk of our new members for the year! In the health insurance world, Open Enrollment is the period during which individuals and employees can enroll in health insurance, make changes to their coverage, or cancel their plans.

Last year, during “OE” (as you’ll hear it affectionately shortened at Oscar), ~100,000 new members logged into Oscar’s site or app for the very first time. This year, we hope to welcome tens of thousands more, and are excited to have them enjoy our new and improved digital onboarding experience.

For many of our new enrollees, particularly those joining us from the government’s Affordable Care Act marketplaces, our onboarding experience is their first introduction to Oscar as a design and technology-enabled health care company that puts its members first. The burden of showing that we take this mantra seriously is daunting but exciting — it’s our chance to undo a lifetime of bitter experiences many of our new members have had with the industry’s incumbents. While we’re constantly working to improve our experience for all aspects of our product, we’ve taken pains to perfect the series of steps — digital, personal, and otherwise — that shape our newest members’ early opinions of Oscar.

Our approach to onboarding new members is holistic — it spans a variety of experiences across multiple touchpoints. No matter how a member chooses to get to know us, we want them to come away with the same feeling of excitement, and be guided through each of the steps that will equip them for success. We use these formative moments to educate them as much as possible about who we are and how we do things differently. The feedback we’ve received suggests that our efforts are paying off:*

“I’m downright obsessed with my healthcare provider, @OscarHealth. Their onboarding experience is more wonderfully crafted than any product I’ve used in the past few years.”

“I’ve been with @OscarHealth for less than a month and freaking LOVE their customer service. Thank y’all for being you.”

So how does it work?

It starts with our enrollment experience. For those who choose to sign up directly through our website (as opposed to through the marketplace or through a broker), we’ve made picking a plan as simple as possible, with personalized, side-by-side comparisons of cost shares and premiums. Throughout the enrollment flow, we are sure to capture all the information we will need to stay in touch throughout the year — an email address, backup phone numbers, and more.

For those who sign up through the marketplace or broker, we send a friendly welcome email that prompts them to set up their digital account to get started with the onboarding process — and we (politely) “chase” them if they don’t.

Once the member has created an account they move on to our onboarding checklist, which focuses on a handful of important actions pre-coverage members should take: learning about our product (e.g. 24/7 access to virtual physicians, cash rewards for meeting daily steps tracking goals), paying their first bill to guarantee coverage, setting up their account preferences, authorizing family members to speak to us about their health, and completing a health questionnaire.

This fall, all new members will experience a revamped digital onboarding flow that we A/B tested and tweaked throughout our last OE period (it was designed by Gabe Schindler and Emili Hsu, product managed by Sahir Jaggi, built by Joseph Botros, Paul Hou, and Eduardo Zapata, workshopped and Oscarized by Olivia Witte, and analyzed brilliantly by Clare Lynch). The new flow includes a number of improvements over the experience we had last year. For example, we made the decision to move the payment option earlier in the flow. Our rationale: we learned this is really the first thing a member wants to do after familiarizing themselves with what we offer, and a delay in payment could be the difference between having or foregoing coverage for the year. Why make them wait?

The results validated our hypothesis: in the experimental group, we saw a 7% reduction in the share of members calling in to pay their first bill over the phone after logging in — an act of frustration for members who wanted to immediately pay that was fortunately within our control to alleviate.

Another update in the latest round of enhancements was to make it even easier for members to access a digital version of their ID card instead of waiting for the physical card to arrive in the mail. This is particularly important for the huge numbers of members who enroll in late December (enrollment volumes spike at the end of OE) and immediately try to schedule January appointments with hard-to-book specialists.

For those who can wait, we send the physical ID card a week or two later, nestled inside one of our meticulously assembled Welcome Kits, a fun and accessible illustrated intro to Oscar that includes a how-to guide for health insurance (complete with Oscar branded band-aids), and of course reminds our members to create a digital account with us.

At any point in this process, if a renewing or new member has questions, they can call Concierge, which, for those who aren’t familiar with it, is Oscar’s answer to customer service: a dedicated group of “care guides,” nurses, and social workers focused on helping members make informed decisions about how and where to get care. Essentially, we’ve reimagined the mundane and impersonal health insurance call center as an opportunity to get to know our members really well. This team like all things at Oscar is tech-enabled!

Once coverage starts, new Oscar members are automatically assigned to a “Concierge Team” based on everything we know about them. Members living in adjacent neighborhoods of Manhattan on similar plans all reach the same group of people when they call us, and their care guides have experience navigating the city’s labyrinth of hospitals and health resources. Spanish-speaking members join a bilingual team. We even have a dedicated team for members awaiting transplants, one of the many ways we make use of information collected from our digital health questionnaire.

When a member calls in, Concierge is ready for them with instructions on how to get started with Oscar. The talking points they use are powered by a homegrown version of “If This Then That,” which we’ve dubbed Automat. Regardless of the reason the member had for calling, the care guide will see instructions on what onboarding steps the member has yet to complete and can walk them through it after answering their questions.

In all of these interactions, we embrace our product principles of making health care simple and accessible. And we remind ourselves that a member’s trust is a delicate thing — earned with great difficulty and lost at the first sign of complexity or the impression that we don’t have their best interests at heart. So far this approach has paid off: 87% of Oscar policyholders have created an online account and in a given month 45% of policyholders use our digital tools on web and mobile to track their steps, access medical bills, pay their premium, research doctors, talk to a virtual PCP and more.

Here are some more things new members have said about our onboarding experience:

“Day 3 with Oscar and I couldn’t be happier. In bed sick, requested to speak with a Dr, and within an hour, Dr called, and she was awesome. Amazing customer service, great Dr. and I’m off to get my RX. Keep up the great work Oscar!!! Wish I had you sooner!!!!!”

“I won’t lie if I say one of the reasons I chose @OscarHealth as my health insurance was because of their design system and the amazing #UX.”

“Just received my starter kit and it is so engaging and well put together.”

“New to the Oscar fam this year. Gotta say: loving the app. It’s so clean and easy to use.”

“THANK YOU, for making everything insurance related so easy and simple. The website is amazing! Never been so stoked about Insurance.”

“2 months in: impressed w/ @OscarHealth. This is the future of healthcare. No more shrouded policies or terrible custsvc… I have a 24/7 on-call doc I can text/call for help/prescriptions. My concierge speaks English and is happy. I just made $12 for my steps.”

Making the most of member engagement is another product principle of ours, whether it’s their first login, their tenth phone call to Concierge, or their hundredth time syncing their steps in the app. Onboarding is a precious opportunity to make sure our members are set up for success and to lay the groundwork for them to turn to Oscar as a trusted advisor in getting the care they need.

Considering Oscar? Here’s how to sign up.

  • All feedback quotes collected from Facebook and Twitter.

Want to talk more tech? Send our CEO, Mario, a tweet @mariots

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