Working the Oscar Magic: A Story of Extreme Growth, A Mighty Team, and Oscar’s Building Blocks

Oscar Health
Oscar Tech
Published in
6 min readMar 1, 2022
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By Brenton Caldwell

Our Product team loves to solve fun, exciting, and challenging problems! And perhaps, there is no better “problem” to have than high membership growth. In Oscar’s insurance business, where we add the majority of our new members during a 3-month span at the end of the year (a window called Open Enrollment Period), staffing up to support new members presents a unique challenge. This year, Oscar grew from ~500K members to more than 1 million members in three months. The pressure was on for us to provide our new and renewing members the best onboarding experience possible!

We believe the ideal onboarding experience welcomes members with…

  • A seamless digital onboarding journey (more on that to come in a future Blog post)
  • Fast answers to simple questions through multiple communication channels
  • Easy access to our Care Team for complex questions (read: a quick average speed of answer & secure message response time)

To ensure we serviced our members effectively, we pulled together a group of rockstars from Product, Data Science, Service Operations, Member Engagement, and Engineering. When we create a team such as this one, an Executive sponsor helps ensure cross-functional buy-in and enables us to move quickly against the opportunity. The structure of the team makes it nimble and capable of quick decision making, something that was extremely important as we needed to roll out our solutions by January 1st … and it was November 29th, only 33 days and counting!

The Clock Strikes December 1st: Choosing Our Building Blocks & Generating Content

The Avengers-style team is assembled, and we’re ready to build! With less than a month to make the most impactful changes, we started to identify the Oscar building blocks we could use to create a richer onboarding journey. Outside of the digital experience, how would we ensure fast answers to simple questions and make sure new members calling in could get ahold of a Care Team member quickly? We settled on using three building blocks from our Tech and Operational tool kit:

  1. [Tech] Automat: an automation system which can trigger all types of communications (highlighted in this blog post)
  2. [Tech] Dreamphone: our call handling, routing and IVR (interactive voice response) platform.
  3. [Ops] Content Management: we’ve integrated an off-the-shelf content management system into many Oscar tech components enabling ops teams to independently iterate on knowledge base content displayed both internally and externally.

After settling on the building blocks we wanted to use, we developed or adapted a lot of content to help address a range of common onboarding questions such as: “when does my ID Card arrive?” or “how do I make a payment?”. These answers already existed across the “Oscarverse,” but were not readily served up to members in some of our most common interaction channels.

The Clock Strikes December 13th: Combining Our Building Blocks and Content

Once we had the content developed, it was time to start our automation journeys!

  • Fast answers to simple questions through multiple channels
  • Use Automat and Natural Language Processing (NLP) to scan incoming secure message threads, determine if the message is a candidate for one of our content-based responses, and trigger a message to the member with an answer.
  • Use Dreamphone and modifications to our IVR to more accurately determine a caller’s intent, surface tips and self-service opportunities around that topic, and then connect to a Care Team member for further assistance (when needed).
  • Use our Content Management System to update and reorder all Frequently Asked Questions so that key onboarding questions and their answers were always upranked.
  • Ease of getting ahold of a Care Team member for complex questions (read: a quick average speed of answer)
  • By offering self-service options at every touchpoint, we freed up the phone lines for more complex questions, boosting Care Team capacity and driving ASA (average speed of answer) down.

The Clock Strikes December 24th: Shipping Our First Set of Automations & Experience Updates

January 1st is quickly approaching and we have already shipped some of our first automations:

  • First secure message automation is up and running for the most common types of plan change requests
  • All FAQs are updated and we added banners / redirects to drive traffic to the newly expanded knowledge base
  • Modifications are made to our phone system to double down on an intent based model with new self-service options

The Clock Strikes January 1st: Beating the Buzzer with Our Last Automations & Experience Enhancements

We race to the finish around here, but we wouldn’t have it any other way! Before our team turned into pumpkins on January 1st, we were able to complete the following:

  • Greatly expanded the scope of our secure messaging automation to address top member questions
  • Phone system intent-based model fully translated to Spanish to make sure we’re effectively supporting our Spanish-speaking membership
  • FAQs fully translated into Spanish as well

To determine if our efforts were successful, we needed to dive into the data! At Oscar, we love data driven insights (see some of our recent data posts here), so we made sure all our engagement funnels were properly instrumented.

The Proof is in the Pudding? Actually, it’s in the Data!

As you might have seen in a recent press release, we grew to over 1M+ members up from ~594K in September 2021. That’s a lot of growth, but the solutions we put in place were able to dramatically streamline our members’ onboarding experience.

  • Fast answers to simple questions through multiple channels
  • We were able to answer a huge number of questions through our secure messaging automations with an average of ~73.5% first-message resolution rate (meaning: no subsequent phone call or secure messaging interaction was needed)

Secure Message Automation Performance

Data about Secure Message Automation Performance
  • We were able to answer tens of thousands of questions through our phone system automations, representing about ~12% of all inbound calls

Phone System Automation Performance

Data showing overall IVR performance
  • We were able to answer a lot more questions with our FAQ updates and saw that ~80% of users who visited our FAQ portal did not have a follow-up interaction (e.g., phone call or secure message) within 48 hours

FAQ Performance

Data on FAQ performance
  • Ease of getting ahold of a Care Team member for complex questions (read: a quick average speed of answer & secure message response time)
  • During the first two weeks of January our average speed of answer for phone calls was ~8x faster compared to last year.
  • During the second two weeks of January, normally a time when health insurance businesses, especially in the ACA, are swamped, our average call response time was ~14x faster compared to last year, which we were thrilled about!
  • The best part about it all is that our Customer Satisfaction scores remained high — meaning that our automations weren’t disruptive to the experience and in fact improved it by answering questions faster than ever before.

So there you have it! That’s how a rapidly formed team of Oscarians ran after a large opportunity to make the Oscar Magic work even better for our new members — all in the span of just one month.

Welcome to our new members, we’re excited to have you aboard!

Brenton Caldwell is a Senior Product Manager working on powering Oscar’s internal communication infrastructure

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

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