Join the team that’s transforming an industry

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Work at Olive

Challenging the status quo, every day

See what it's like to be part of a team that's transforming healthcare and innovating every step of the way.

Our core values

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Choose vision over status quo

Obsess like lives depend on it

Act with urgency

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Welcome to The Grid

Learn how our innovative distributed work model has helped access top-tier talent to build an asynchronous team across the U.S.

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.

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Free or affordable health insurance plans

Grid stipend

Unlimited PTO

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Telemedicine and EAP mental health resources

Wellness programs

Getaways by Marriott Bonvoy

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Family-building and fertility support via Kindbody

Three months paid parental leave

401k match

Employee Resource Group

Employee resource groups

Volunteer time and opportunities

This link leads to the machine-readable files that are made available in response to the federal Transparency in Coverage Rule and includes negotiated service rates and out-of-network allowed amounts between health plans and healthcare providers. The machine readable files are formatted to allow researchers, regulators, and application developers to more easily access and analyze data.

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Encouraging employee growth

Olive supports internal talent with programs for personal and professional growth. The Choose Growth in Leadership and the Women in Leadership programs enable managers and talented individuals to gain new skills and advance to the next level of their careers.

Talent acquisition at Olive

The application process at Olive is simple and straightforward. First, take a look at our open positions and submit our (short) application with your resume. We'll be waiting!

If your experience matches our needs, we’ll reach out to schedule a conversation — and we do mean conversation. This is your chance to put your best foot forward, but also a time for you to ask questions about working for Olive.

Our interview process is where things get interesting. Each functional area at Olive has a different order and process for interviewing, but all include a few behavioral and situational 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 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 ensure that you’re a great fit for us AND we’re a great fit for you! We pledge that if at any point we determine the role is not a fit, you'll receive written or verbal communication from our talent acquisition team.

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

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Work at Olive

We're on the lookout for world-class talent. If you're looking to join a passionate, mission-driven team, check out our open positions and submit an application today.