Senior Director of Operational Compliance

Oscar, Arizona

A better kind of health insurance company

Deliverables: What you have to achieve

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.  Working closely with these embedded experts’ team leads, the Senior Director, Operational Compliance will coordinate their activities while also pursuing company-wide compliance initiatives.  The overarching goal is to ensure that, in all states and lines of business, Oscar’s functional areas operationalize new laws and regulations pursuant to documented policies and procedures, monitor their own performance against these policies and procedures, are both audited and audit-ready, and remediate as required.  Based in Oscar’s Tempe, AZ Health Hub, the Senior Director, Operational Compliance will report to the NY-based Vice President, Compliance and Regulatory Affairs (Compliance Officer).


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 review Oscar’s standards and practices regarding policy and procedure development and design; reporting on operational monitoring; operational audits; and Corrective Action Plans (“CAPs”)

By the end of month 3, you will:

  • Collaborate with direct reports to articulate a plan for all compliance requirements to be identified, articulated, and monitored by functional teams
  • Set company-wide standards (applicable also to delegates, where contracts permit) for the development and justification of operational compliance targets not explicitly established in regulation
  • Educate direct reports in CMS’s Program Audit practices, ensuring that all operational areas are on track for audit-readiness by market entry in 2020
  • Work with the Compliance Officer, Internal Audit / Model Audit Rule Lead, and Finance Department to expand prior Compliance Risk Assessment activities toward a broader Enterprise Risk Management process, while also satisfying the Compliance Department’s requirements for risk-based Work Plan development
  • Contribute and coordinate all Operational Compliance inputs to the Compliance Work Plan, including identifying needed audits of higher-risk functions
  • Work with the Compliance Officer and Legal Department to develop practices for the articulation and assessment of compliance, legal, and operational risks underlying business decisions, and for the codification of such decisions once made
  • Begin work with Oscar’s technical teams to develop options for implementing record retention policies in a paperless environment
  • Meet with direct reports to identify strengths and areas for development, and work with them to set role-specific and professional development goals for the coming year

Afterwards and on an ongoing basis, you will:

  • Explore and, as appropriate, implement technical solutions to avoid undue policy and procedure proliferation as Oscar expands rapidly into new markets
  • Building on (and, where appropriate, in coordination with) direct reports’ efforts to ensure that all operational policies are tied to monitoring mechanisms, lead a company-wide project to automate the reporting of key compliance metrics to the Corporate Compliance Committee and external auditors/reviewers
  • Work with the Compliance Officer, Internal Audit / Model Audit Rule Lead, and Finance Department to refine and broaden the Enterprise Risk Management process
  • Define the lower and upper bounds of CAP applicability, and refine or replace existing risk dashboarding tools – drawing on but not limited to the Enterprise Risk Management / risk assessment process – to address risks or noncompliance exceeding this upper bound
  • Develop a structured means of cooperation or coordination with the Internal Audit / Model Audit Rule Lead to ensure that all high-risk functions are audited or tested, while minimizing duplicative or overlapping asks of functional leads
  • Develop and execute on a plan for maintaining all operational areas in a state of permanent audit-readiness, including for CMS Program Audits
  • Promulgate standard templates and best practices enabling an increased frequency and intensity of Compliance audits of functional areas
  • Lead the company-wide implementation of record retention practices
  • Lead the Compliance Department’s participation in Business Continuity and Disaster Recovery efforts
  • In a structured and consultative manner, build the Operational Compliance team’s remit to include all operational areas across Oscar
  • Maintain close communication between, and make periodic in-person visits to, Oscar’s New York- and Tempe-based Operational Compliance teams
  • Foster the role-specific goals and professional development of direct reports, including working with them to develop and scale their own teams sustainably


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
  • 10+ years’ experience in a healthcare compliance setting (ideally at an insurer), including both managing teams and guiding (your or other) teams through regulatory audits
  • 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

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 can manage managers while setting directions for your full vertical
  • 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.

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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