Hi, we're Oscar. We're hiring a Staff Security Engineer, GRC to join our Information Security Team.

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

About the role

As a Staff GRC Engineer, you will be a cloud-aware governance, risk, and compliance expert supporting Oscar's healthcare technology environment, with a specific focus on CMS Enhanced Direct Enrollment (EDE) platforms and stage 3 certification readiness. You will translate CMS EDE requirements, FedRAMP Moderate-aligned expectations, and NIST SP 800-53 controls into practical control designs, compliance-as-code patterns, evidence workflows, and risk management practices for AWS-hosted and Azure-hosted systems. You will operate as a senior subject matter expert who can partner directly with engineering, security, legal, compliance, product, and CMS-facing stakeholders to keep regulated platforms audit-ready while enabling secure delivery.

You will report into the CISO.

Work Location: This position is based in our New York City office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $245,916 - $286,902 per year You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants, and annual performance bonuses.

Responsibilities

CMS EDE Governance: Lead governance and compliance strategy for CMS Enhanced Direct Enrollment platforms, with a focus on Phase 3 certification expectations, ongoing oversight, audit readiness, and regulator-facing evidence.
Control Architecture: Map CMS EDE and NIST SP 800-53 requirements to technical, operational, and administrative controls that can be implemented and measured across AWS and Azure environments.
Significant Change Management: Prepare, review, and submit CMS significant change requests, partner with technical teams on impact analysis, and maintain clear evidence of approval status, risk decisions, and implementation readiness.
Compliance as Code: Build and mature compliance-as-code patterns for AWS, including control automation, policy-as-code, infrastructure-as-code guardrails, continuous evidence collection, and automated drift detection.
POA&M Management: Own POA&M lifecycle management, including issue intake, risk rating, remediation planning, dependency tracking, stakeholder reporting, evidence validation, and closure readiness.
Risk Assessment and Advisory: Perform risk assessments for cloud services, EDE platform changes, system integrations, third-party dependencies, and security exceptions using healthcare and federal control expectations.
Audit and Evidence Operations: Build repeatable evidence workflows for CMS audits, independent assessments, internal reviews, and customer or partner assurance requests.
Cross-Functional Leadership: Serve as a trusted GRC partner to engineering, security, product, compliance, legal, and business leaders, translating regulatory requirements into practical technical plans.
Compliance with all applicable laws and regulations
Other duties as assigned

Requirements

7+ years of combined experience in governance, risk, compliance, cloud security, security engineering, audit, or regulated technology environments.
Deep working knowledge of CMS Enhanced Direct Enrollment requirements, including the ability to support or lead Phase 3 certification activities.
Strong knowledge of NIST SP 800-53 controls control expectations, including how those controls map to cloud-hosted healthcare platforms.
Hands-on experience partnering with engineering teams to implement controls in AWS using infrastructure as code, policy as code, automated evidence collection, or similar compliance automation approaches.