Sr. Staff Security Engineer – AI, VMR, Offensive Security

Why Join GEICO?

At GEICO, we offer a rewarding career where your ambitions are met with endless possibilities.

Every day we honor our iconic brand by offering quality coverage to millions of customers and being there when they need us most. We thrive on relentless innovation to exceed our customers' expectations while making a real impact on local communities nationwide.

Founded in 1936, GEICO is a member of the Berkshire Hathaway family of companies and one of the largest auto insurers in the United States. When you join our company, we want you to feel valued, supported, and proud to work here. That's why we offer the GEICO Pledge: Great Company, Great Culture, Great Rewards, and Great Careers.

GEICO is seeking a highly experienced Senior Staff Security Engineer to lead the strategy and technical execution of Vulnerability Management and Offensive Security across a complex, hybrid technology ecosystem. This role blends deep security engineering expertise with strong architectural leadership, hands-on experience, leveraging frontier AI models for security, drive customer success, and provide advisory to senior executive leaders.

This is a high‑impact hands-on technical role who maintains a strong connection with both customers and underlying systems for shaping the company’s vulnerability management maturity, influencing engineering culture, and safeguarding critical systems. The Senior Staff Security Engineer will drive meaningful, measurable improvements to security posture while enabling teams to build and ship technology with confidence. They drive customer success for the vulnerability management and offensive security functions. They demonstrate a keen ability to dive deep into complex problems to fully understand how systems operate, discerning when to make incremental improvements and when to challenge the status quo to drive impactful results. They are well-versed with Vulnerability Management Lifecycle - asset discovery, internal/external scans, contextualization and risk-based assessment, triaging of CVEs, detection authoring, security data pipeline, reporting, and remediation.

This role is an advisor to executive leaders and is critical to our cybersecurity objectives. The position requires a strong security and engineering background with hands-on experience. The successful candidate will play a key role in maintaining a strong security posture for the company through close collaboration with infrastructure, development, product, and other organizations across GEICO to integrate security into the ecosystem from design through deployment to sustainable operations.

At GEICO’s Cybersecurity organization, we are committed to strengthening the company’s digital resilience and advancing the security of our technology ecosystem. Our mission is to proactively protect our customers, associates, and business by modernizing our security capabilities, elevating our defensive posture, and enabling secure innovation at scale. As GEICO transforms its technology landscape, Cybersecurity plays a pivotal role in delivering secure, reliable, and future‑ready solutions that support every line of business and every customer channel—empowering the enterprise with protection that is adaptable, intelligent, and built for the evolving threat landscape.

What do you bring in?

This role is designed for a highly technical, hands-on security engineer who thrives at the intersection of vulnerability management, offensive security, and emerging AI-driven threats and defenses. You bring deep domain expertise across penetration testing, red and purple teaming, and modern security engineering, coupled with the ability to leverage AI to scale both offensive insights and defensive capabilities. You are customer-obsessed in your approach to security, operating with a strong sense of ownership and urgency in a fast-paced environment. You excel at translating complex technical risks and security concepts into clear, business-aligned outcomes that resonate with senior executives and drive action. A self-starter by nature, you navigate ambiguity with confidence, independently overcome challenges, and consistently deliver measurable results. You are equally comfortable advising executive leadership as you are designing and building secure systems, bringing a rare blend of strategic influence and deep engineering execution to elevate the organization’s security posture.

Key Responsibilities

VM & OffSec Execution

Lead the strategy and technical execution of Vulnerability Management, Offensive Security, and AI-augmented security at scale.

Lead the full vulnerability lifecycle: discovery, validation, risk analysis, prioritization, and remediation measurement.

Leverage business contextualization, underlying systems, threat intelligence, and AI frontier models to perform risk assessment for identifying true risk to drive remediation.

Integrations among scanning tools, asset inventory, CMDBs, ticketing, CI/CD, and monitoring pipelines to streamline workflows.

Evaluate, test, and implement emerging AI technologies that advance automated discovery and remediation.

Design automation to reduce manual work, increase accuracy, and accelerate remediation.

Generate data‑driven insights that help teams understand, prioritize, and resolve vulnerabilities efficiently.

Cross‑Functional Partnership

Drive customer success for the vulnerability management and offensive security functions.

Play role of an advisor to senior executive leadership.

Collaborate with cloud, infrastructure, DevOps, and product engineering groups to integrate vulnerability management into pipelines and delivery workflows.

Work closely with risk, compliance, governance, and incident response teams to ensure alignment with organizational and regulatory standards.

Communicate vulnerability trends, risk implications, and remediation strategies to technical and non‑technical stakeholders.

Operational Excellence & Measurement

Define KPIs, SLAs, dashboards, and reporting models to drive accountability and measurable vulnerability reduction.

Establish repeatable processes, playbooks, and workflows that ensure consistent VM operations across teams and environments.

Ensure the reliability, performance, and scalability of VM tools and data pipelines.

Leadership, Mentoring & Team Development

Mentor junior and mid‑level engineers, offering guidance on advanced security concepts, engineering best practices, and career development.

Serve as a multiplier by elevating skillsets across teams through coaching, pairing, design reviews, and knowledge‑sharing.

Influence architecture and engineering leadership with clear communication, strong decision‑making, and the ability to simplify complex security issues.

Required Qualifications

10+ years of experience in cybersecurity or security engineering roles.

Deep expertise with vulnerability management tools, methodologies, and industry standards.

Hands‑on experience with modern infrastructure, cloud services (AWS/Azure/GCP), container platforms, and operating systems.

Proficiency with a modern programming language (Python, Go, Java, etc.) and scripting for automation at scale.

Strong understanding of security architecture, networking, operating systems, identity, and cloud services.

Proven ability to lead, mentor, and inspire engineers across multiple teams.

Strong communication skills with the ability to influence senior stakeholders and translate complex risks into actionable guidance.

Hands-on experience implementing cybersecurity frameworks e.g. NIST CSF

Hands-on experience with leading compliance initiatives to meet e.g. PCI, SOX, NYDFS, etc.

Preferred Qualifications

Exposure to comprehensive security assessment, penetration testing, threat modeling, or security research.

Familiarity with SIEM, SOAR, and asset intelligence integrations.

Security certifications (CISSP, GCSA, OSCP, cloud