Oscar’s Hackathon Playbook

by Duncan Greenberg

Last month, Oscar hosted its latest Hackathon, an exciting 2-day sprint that has become one of the company’s most time-honored traditions. In total, there were 25+ projects and 100+ participants, with submissions ranging from dev tools to member experiences to virtual care concepts, and even a few comic setpieces. Hackathons are a chance for our teams to flex creatively, collaborate with people they don’t normally work with, and have a lot of fun in the process. As a bonus, they often produce new ideas that help us serve our members or employees more successfully.

In the July Hackathon, one team built a new feature called “Picture Search,” which lets members take a photo of a pill bottle through the app to check whether a drug is covered and how much it will cost to refill.

Hackathons in tech are not uncommon, but Oscar’s are unique in a few ways:

• They’re not just for tech. Everyone at the company is encouraged to participate. Many Hackathon teams don’t have a single engineer, designer, or product manager.
• Leaders at all levels participate. In the most recent one, Oscar CEO Mario Schlosser held office hours to brainstorm ideas with teams and launched his own project. For others looking to organize their own, this commitment from above helps employees feel comfortable carving out the time.
• The time is protected. While not a formal company holiday, for two days, teams set aside their day-to-day work to focus on exciting, radical, meaningful, and/or funny ideas. We actively police meetings and other obligations that intrude.
• They’re not just once a year. Early on, Oscar’s Hackathons were an annual tradition, but a few years ago, they shifted to a more frequent cadence (2–3 times a year). Monthly would obviously be too often (they’re a blast but can be exhausting). Once a year meant people were sitting on ideas for far too long. They were temporarily dialed back during the pandemic to avoid adding to feelings of burn-out, but this July marked their return.
• We try to productionize ideas (but only when it makes sense). Most Hackathon projects end up withering on the vine as teams shift back into their routines — and that’s okay since the primary goal is for people to explore ideas they’re passionate about and make new connections with colleagues. In fact, we explicitly encourage people to pursue ideas that are *not* on their road maps. But when there are projects that we believe could meaningfully enrich our member experience or make employees’ lives easier, we work to ensure they’re appropriately prioritized.
• We apply similar techniques in our everyday work. We’ve learned that focused time, free of the “productive” maelstrom of emails, Slack messages and stand-ups, is the key to making progress on complex problems — the kind of problems that are pervasive in healthcare. For this reason, Hackathon-like design sprints are a popular practice at Oscar, especially when teams are looking to jump-start their thinking on greenfield ideas.

Here’s a simple playbook you can use to run your own:

• Collect ideas: use a Google form, Google Sheet, Trello Board, Monday.com board, or Slack workflow to gather ideas from across the company. That way, folks know which projects are in the works and can pitch in or draw inspiration. Sometimes we set a theme for the Hackathon though we generally let people work on whatever excites them.
• Hold a pitch session: everyone gets 1 minute or less to describe their idea and drum up collaborators. Hearing other people’s ideas gets people into a creative mindset and fosters participation from folks who don’t want to lead a team.
• Set up a central hub: we use a Slack channel as the place for participants to ask questions about the process, connect with other teams, share their real-time reactions to the pitches and presentations, give kudos to the winners, and more.
• Select your judges: ours usually includes a mix of leaders from design, eng, and product.
• Pick your prizes: by far the biggest reward is participating in the process itself. But having some cool gadgets to bestow on teams that chart new and impressive territory, adds an element of festive competition to the proceedings.
• Hold a kick-off: company leadership uses this time to welcome all of the participants and officially launch the 2-day sprint. We also share details on the format for presentations. Meghan Joyce, our Chief Operating Office, MC’d our July kick-off.
• Regroup for presentations: at the end of the two days, we invite all of the teams back to share their results. Before the pandemic, teams would present live using slides and in most cases live demos. In today’s remote world, we opted for pre-recorded demo videos, no more than 2 minutes in length.
• Announce the winners: we spread the wealth by picking multiple winners, one for each of several categories. We design our award categories to make sure there’s a healthy mix of technical and non-technical innovation as well as explicit support for teams to work on projects that create a more welcoming and inclusive environment for members and employees.

Here are just a few projects from Hackathons past, a number of which ultimately made it into production:

In-app Notifications

In early 2020, Hackathon teams rallied around ideas to help our members navigate the pandemic, including a new configurable in-app channel for our marketing team to help members stay on top of public safety guidelines as well as vaccination and testing options. This new entrypoint is one of the reasons why our homegrown COVID-19 risk assessment tool was so widely used by members in the early days of the pandemic.

Content Assistant

A product manager observed that care guides often sent similar messages to members in response to common questions about coverage and mobilized a team to build a new tool for surfacing pre-scripted messages (written by our product marketing team) with dozens of variables to personalize the content and automatic translation. These messages are now in routine use, providing members with high quality answers, faster than ever before.

Emotiqueue

An engineer decided to create a queueing system for anyone at Oscar to request a new emoji on Slack. Emotiqueue v2 debuted at the July Hackathon.

Automated Mobile Regression Testing

An engineer wanted to unburden the product managers (and fellow engineers) in his area by automating regression testing (i.e. QAing existing features) for mobile releases.

Oscar Swag Store

A group of Oscarians wanted to expand the options for employees to stock up on Oscar branded clothing and accessories.

Baby Monitor

A product leader wanted to celebrate happy moments in our members’ lives. In v1, a light would illuminate in the office all hands area every time a baby was born. In v2, during the pandemic and with the office not yet fully reopened, we shifted to Slack.

Oscar Coffee Roulette

A Hackathon team wanted to facilitate new friendships across the company.

Duncan Greenberg, the VP of Product, Care & Coverage Experience, oversees Oscar’s product teams focused on digital member experience, customer service technology, virtual care platform, and automation engine.

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