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Oscar Health // health insurance
New York City    Posted: Thursday, January 21, 2021
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Hi, we're Oscar. Were hiring a Workday Systems Architect to join our People Operations team in our New York office. 

Oscar is a technology-driven, consumer-focused health insurance startup founded in 2012 & headquartered in New York City. Our goal is to make health insurance simple, transparent, & human. We need your help to do so.

About the role:

The People Team is the linchpin of Oscars values & culture--we bring, we build, we maintain, we strengthen. As the Workday Systems Architect you will enhance & leverage our HR systems & best practices to build & improve the processes necessary to support our employee base. In this role, you will partner with IT, HR & stakeholders across the organization to provide proactive technical solutions to support business needs. By identifying opportunities for improvement, executing on those improvements through innovation, & leveraging our current technology, you will create & provide an exceptional employee experience to the organization.

You will report into the Senior Director of People Operations.


  • Design, develop, implement, support & optimize Workday configuration to meet business processes, capabilities & needs
  • Design, build, test & deploy Workday HCM solutions, including creating test scripts, remediation plans, & hypercare support
  • Work closely with the business to understand functional requirements & execute them through successful implementation, testing & deployment with required documentation
  • Successfully juggle multiple projects & priorities, while shifting direction as priorities change
  • Proactively find inefficiencies in processes, suggest enhancements, & present proposals to stakeholders
  • Foster ongoing Workday relationships & customer partnerships within user groups and/or the Workday community to ensure understanding of current & new functionality available


  • 5+ years of experience configuring Workday
  • Bachelors degree or equivalent experience
  • Experience navigating cross-module & downstream configuration impacts
  • Experience working across a variety of Workday modules
  • Experience partnering with internal stakeholders to identify opportunities for solutions, translating technical requirements to business needs, & vice versa
  • Microsoft Office proficiency

Bonus points:

  • Experience working for a public company
  • Experience with Greenhouse or other Applicant Tracking Systems (ATS) 
  • Experience with Shareworks (equity management system) 
  • Experience with Benefits & Payroll modules in Workday
  • Workday Implementation experience

Life at Oscar: 

At Oscar, being an Equal Opportunity Employer means more than upholding discrimination-free hiring practices. It means that we cultivate an environment where people can be their most authentic selves & find both belonging & support. We're on a mission to change health care -- an experience made whole by our unique backgrounds & perspectives.

We aim to make health care affordable & accessible for all, & apply this same vision to our perks & benefits, including: medical benefits, unlimited paid-time off, paid parental leave, retirement plans, company social events, stocked kitchens, wellness programs, & volunteer opportunities.

Reasonable Accommodation:

Oscar applicants are considered solely based on their qualifications, without regard to applicants disability or need for accommodation. Any Oscar applicant who requires reasonable accommodations during the application process should contact the Oscar Benefits Team ( to make the need for an accommodation known.

Pay Transparency Policy:

Oscar ensures that you won't be discharged or discriminated against based on whether you've inquired about, discussed, or disclosed your pay. Read the full policy here.

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