Director of Operational Compliance

Oscar, Arizona

A better kind of health insurance company

By 2020, not only will Oscar offer commercial products beyond our nine current states, but we will also begin to offer Medicare Advantage (“MA”) products. As we expand into new geographies and lines of business, we have restructured our Compliance Department to “embed” Compliance subject-matter experts in most operational departments.  The Director, Operational Compliance will shape the roles, responsibilities, and successes of these new Compliance roles – ensuring that, in all states and lines of business, Oscar’s functional areas operationalize new laws and regulations, monitor their own performance against regularly updated policies and procedures, and are both audited and audit-ready.  The Director, Operational Compliance will report to the Vice President, Compliance and Regulatory Affairs.


Deliverables: What you have to achieve

In your first six weeks, you will:

  • Familiarize yourself with Oscar’s structure, operations, and risk assessment and mitigation activities
  • Work with direct reports to set company-wide standards for policy and procedure development and design; reporting on operational monitoring; and operational audits

By the end of month 3, you will:

  • Roll out the new standards for policies and procedures, monitoring, and audits
  • Develop a work plan for audit-readiness, including close work with the Director, Core Compliance to prepare for the pre-market-entry CMS audit of Oscar’s MA program
  • Identify key compliance metrics in the commercial and MA markets for reporting to the Corporate Compliance Committee
  • Work with the Legal Department to develop a structured process for the interpretation, dissemination, and implementation of new laws and regulations

Afterwards and on an ongoing basis, you will:

  • Work with operational teams to automate the processes by which business areas are monitored for compliance with governing laws and regulations
  • Work with the Director, Core Compliance to develop structured processes for Oscar’s response to audit activities, including CMS Program Audits
  • Ensure that Oscar’s Operational Compliance Team scales appropriately as Oscar continues to grow
  • Maintain close communication between, and make periodic in-person visits to, Oscar’s New York- and Tempe-based Compliance teams
  • Collaborate and coordinate with Oscar’s Internal Audit function to alleviate duplicative activities while holding business functions to account


Winning factors: What leads to success

We are looking for someone with a deep knowledge of the commercial and MA markets who will promote a culture of compliance, ethics, and audit-readiness across all of Oscar’s operations.


Must-have qualifications and expertise include:

  • College degree
  • 9+ years’ experience in a healthcare compliance setting, including managerial experience
  • Experience growing and scaling a team and increasing operational efficiency in fast-paced environment or at a start-up

Preferred qualifications include:

  • CHC, CCEC, or similar
  • Experience with MA compliance, including undergoing a full CMS Program Audit
  • Experience with HIPAA, data privacy, or data security processes

We think you will be successful if...

  • You are a critical thinker who can distill complex concepts and regulatory requirements into easy to understand action items
  • You have acute attention to detail and always strive for perfection when writing formal documents.
  • You get things done, even if it’s crunch time
  • You enjoy working in a collaborative environment and working cross-functionally with all business areas within the organization
  • You are personable, self-starting and organized
  • You have a passion for healthcare and a knack for making processes more systematic

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

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

Pay Transparency Policy: Oscar's Pay Transparency Policy 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.

About Oscar

Founded in 2012, Oscar is probably the last thing you would expect from a technology startup – a seemingly old-fashioned healthcare insurance provider. The company provides clients with the kind of clarity and simplicity we have come to expect from an e-commerce site. And, of course, they're hiring.

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