Staff Security Engineer, GRC

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.

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.

• →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

• 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.
• Experience preparing CMS significant change requests, security impact analyses, POA&Ms, audit evidence, control narratives, risk acceptances, and remediation plans.
• Ability to communicate regulatory and control requirements clearly to technical and non-technical audiences, including senior leaders and external assessors.

• Bachelor's degree or years of equivalent experience.
• Prior work experience in healthcare, health insurance, marketplace exchange, or other highly regulated technology environments.
• Experience supporting CMS EDE Phase 3 certification, annual CMS audits, independent security assessments, or regulator-facing security reviews.
• Experience with GRC platforms, cloud security posture management, SIEM/evidence pipelines, configuration management, or automated control monitoring.
• Relevant security, audit, or cloud certifications such as CISSP, CISA, CRISC, CCSP, AWS Security Specialty, or equivalent practical experience.