Careers at Olive

The people behind Olive are a passionate team of innovators – every employee here is a game-changing part of transforming the future of healthcare with AI.

Olive is a hyper-growth company that hustles daily to drive our mission forward. All of our teams work together to create the best possible experiences and products for our customers.

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Challenging the status quo – every day

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The Grid –
The future of work

Just like technology, times are changing fast and flexibility is an advantage, now more than ever.

Work from anywhere

That’s why Olivians can work from anywhere.

We call it The Grid – a Distributed Growth Plan, because we believe small teams move mountains and working where you’re most productive is pretty intelligent.

“Monolithic offices are dead. Olive is embracing The Grid: a growth plan where we don’t all have to be physically together to be a highly successful company.”
- Sean Lane, CEO of Olive
People working at desk

The Hub, Columbus, Ohio

So, what’s it mean to be ‘on The Grid?’

To Olive, being “on The Grid” simply means you are actively working. The work model empowers Olivians to work wherever they most effectively drive the company mission forward, be that at home, in a cabin, on the beach, or in one of our offices.

Our headquarters, referred to as The Hub, is proudly housed in Columbus, Ohio, and we have dedicated teams that work at AlphaSites: onsite AI command centers built within customer health systems across the country, as well as sub-stations (workspaces that house 10+ co-located Olivians anywhere in the country).

Customer Map Legend

The best part?

Olivians can freely move from The Hub to any substation across the U.S. based on personal preference or customer needs – we even encourage like-minded Olivians looking to create a substation in a new market to lead the charge.

Today, there are many great benefits of working at Olive – from free health insurance to unlimited PTO, and more – but the ability to work at your best, no matter where you are, creates empowerment in our employees and deep connections in technology communities across America.

The benefits of working at Olive

We take the health and happiness of our employees seriously and consistently evaluate new ways to provide an amazing place to work. From retirement planning, to a wellness program designed to actively incorporate mental and physical wellness into daily interactions amongst fellow Olivians, we make sure to take care of our own.

Health insurance options that start at free

Grid stipend

Unlimited PTO


EAP/Mental health resources

Getaways by Marriott Bonvoy

Family-building and fertility support via Kindbody

Three months parental leave

401(K) match

Wellness program

Olive Getaways: Powered by Marriott Bonvoy™

Olive Getaways powered by Marriott Bonvoy

At Olive, we believe that time off The Grid is just as important as time on. That’s why we encourage our employees to get away from work to relax, explore or try something new – while we foot the bill. Through the Olive Getaways program, every Olivian can receive 200,000 Marriott Bonvoy reward points that can be redeemed for free nights at any Marriott property, airfare, travel experiences, gift cards, events and more. Beach vacay, here you come.

Our core values

Olive Logo

Inclusion & diversity – becoming more human

At Olive, we’ll never be content with the status quo. Not in healthcare, and not in our own company. We challenge ourselves to be more inclusive and diverse every day and in every way. And this is because we believe that through inclusion and diversity, we become our most human. And that’s our mission, to make healthcare—and ourselves—more human.

Talent acquisition at Olive

The application process at Olive is pretty simple and straightforward. First, feel free to learn more about our company and the open positions available. If you spot a position you’re interested in and qualified for, just complete our (short) application and submit your resume.

A member of our talent acquisition team will review your submission and if your experience aligns, we’ll reach out to schedule a call to have a conversation. And we do mean conversation. This is not only your first moment to put your best foot forward, but also a moment to ask questions about the role and working for Olive.

Our interview process is where things can get interesting—for both of us. Each functional area at Olive has a different order and process for interviewing, but all include a few behavioral and situational questions, and, always, time for you to ask questions. For example:


For a sales position, you can expect a virtual “Day in the Life” interview with a team member in that role who can speak to day-to-day expectations.


For a tech position, you can expect to complete a take-home Hackerrank or Woven technical assessment in addition to a “Day in the Life” interview.


For a corporate position, you may be asked to complete a role-based assignment that will be shared with the hiring team.

The goal is: we want to do everything we can to ensure that you’re a great fit for us AND we’re a great fit for you! To that end, we pledge that if at any stage of the process we determine the role is not a fit, you can expect to receive written or verbal communication from our talent acquisition team.

And if you are a great fit—Congratulations! A member of our talent acquisition team will walk you through your offer and Olive’s amazing benefits package.

Open positions

We’re looking for world-class talent and growing fast. Check out our open positions below. Don't see what you're looking for? Check back soon, we're continually adding new positions and hiring at a rapid rate.

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