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.

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.

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.

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.

Bonus Points

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.

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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 and find both belonging and support. We're on a mission to change health care -- an experience made whole by our unique backgrounds and perspectives.

Pay Transparency

Final offer amounts, within the base pay set forth above, are determined by factors including your relevant skills, education, and experience.

Full-time employees are eligible for benefits including: medical, dental, and vision benefits, 11 paid holidays, paid sick time, paid parental leave, 401(k) plan participation, life and disability insurance, and paid wellness time and reimbursements.

Artificial Intelligence (ai)

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Reasonable Accommodation

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 (accommodations@hioscar.com) to make the need for an accommodation known.

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