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Hi, we're Oscar. Were hiring a Senior Manager to join our Benefits Optimization team. 

Oscar is the first health insurance company built around a full stack technology platform & a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselvesone that behaves like a doctor in the family.

About the role:

As Senior Manager, Implementation & Benefits Optimization, you will develop & execute strategies & processes that support consistency, efficiency & overall integrity of benefits administration at Oscar. To accomplish this, you will design standardized tools, templates, workflows, service level agreements, & quality controls to optimize implementation & ongoing management of plans & benefits across a diverse range of clients, markets, & health insurance products. Working with internal & external stakeholders to define plan design & benefit configuration requirements, manage project schedules, identify & manage risks, drive benefit configuration priorities, & coordinate implementation activities.

In partnership with our Insurance Operations & technology teams, you will build scalable & agile benefit configuration strategies, workflows & technical solutions to benefit administration challenges. 

Primary Duties & Responsibilities 

  • Develop & maintain standardized tools & workflows for collecting, documenting, & tracking plan build & benefit configuration requirements.
  • Design, organize & lead process improvement efforts throughout the benefit design & implementation lifecycle.
  • Support resource planning & project scoping activities necessary to implement new platform capabilities & clients. Develop proposals outlining proposed project approach & work plan.
  • In partnership with Oscars Plan Design, Insurance Operations, & tech teams, develop & document standard service level agreements/objectives for plan build & benefit configuration activities.
  • Ensure that overall benefit operations, as well as project-specific, performance metrics are in place & are effectively managed. 
  • Coordinate plan build & benefit configuration activities across projects, identifying & managing interdependencies & ensuring appropriate resource allocation.
  • Establish quality assurance/testing strategies & support the development of test plans.  
  • Support roadmap-planning process, partnering with the Director, Benefits Configuration to define short-term & long-term program goals.
  • Coach, lead & develop Configuration Analysts team to ensure program goals are met.

You will report to the Director of Benefits Configuration. This is a remote role, you are able to work remotely in one of the following states: Arizona, California, Connecticut, Florida, Georgia, Illinois, Maryland, Massachusetts, Michigan, New Jersey, New Mexico, New York, North Carolina, Ohio, Pennsylvania, Rhode Island, Tennessee, Texas, Utah, Virginia, or Washington. Note, this list of states is subject to change.

Required education & experience

  • 6+ years of managing, driving & overseeing large projects and/or designing & executing process improvements, ideally within a managed care/insurance organization.
  • 4+ years of people leadership experience (direct or indirect)
  • Lean Six Sigma Yellow Belt or comparable certification. If an individual does not possess the required certification, then certification must be obtained within twelve months of employment.
  • Successful past application of Lean/Continuous Process Improvement concepts.
  • Experience managing cross-functional teams & complex projects.
  • Experience facilitating/leading requirements gathering processes.

Preferred education & experience

  • Demonstrated ability to use tools to answer your own questions (e.g., SQL/Python)
  • Lean Six Sigma Green Belt or Black Belt certification.
  • Experience in managed care operations, preferably health insurance benefit configuration, claim adjudication, or similar experience.
  • Experience designing test plans.

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 encourage our members to care for their whole selves, & we encourage our employees to do the same with comprehensive medical benefits, generous 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.

COVID-19 vaccine requirements for in-person work: 

To protect the health & safety of our employees, we require any employee conducting in-person work* to be fully vaccinated against COVID-19 by their start date. 

If you are unable to be vaccinated due to medical or protected religious reasons, please reach out to our Benefits team at to submit an accommodations request.

*Note: In-person work includes: employees required to work from our offices (either full-time or part-time), employees conducting sales work in the field & employees conducting at-home or in-person visits with members.

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