Group 1001 is a consumer-centric, technology-driven family of insurance companies on a mission to deliver outstanding value and operational performance by combining financial strength and stability with deep insurance expertise and a can-do culture. Group1001’s culture emphasizes the importance of collaboration, communication, core business focus, risk management, and striving for outcomes. This goal extends to how we hire and onboard our most valuable assets – our employees.
Why This Role Matters:
Group 1001 is seeking a hands-on Senior Offensive Security Engineer to lead penetration testing and red team operations across our cloud, endpoint, application, and API environments. You will be the technical owner of our offensive testing program: planning and performing penetration tests, running red and purple team exercises, managing our private bug bounty program, and reducing our external attack surface.
As our application security and SDLC practices mature, you will also embed with development teams, align testing to their release cycles, and help move security testing earlier in the lifecycle. This role reports to the AVP of Security Lifecycle & Architecture and works closely with Security Architecture, Detection Engineering, Threat & Fraud Defense, and Audit. If additional headcount is approved, you will provide technical direction and mentorship to a second offensive security engineer.
How You'll Contribute:
Plan, scope, execute, and report on penetration tests across Azure, AWS, and GCP environments, endpoints, internal web and desktop applications, and APIs, with clear, prioritized remediation guidance.
Partner with development teams to learn their release schedules, plug testing into their delivery cycles, and help mature application security and SDLC practices.
Lead and perform quarterly red team and purple team operations that simulate real-world adversary tactics to test detection, response, and overall resilience.
Manage the private bug bounty program, including strategy, scope, vulnerability triage, severity validation, and coordination of remediation with internal teams.
Operate the enterprise continuous attack surface monitoring platform, triage external findings, and drive remediation to closure.
Oversee third-party testing vendors, including the annual external penetration test: define scope and objectives, review deliverables, and ensure results align with internal priorities and regulatory expectations.
Validate remediation through retesting and track findings to closure with application, infrastructure, and security owners.
Translate offensive findings into defensive improvements by working with Security Architecture, Detection Engineering, Threat & Fraud Defense, and Audit.
Develop and refine offensive tooling, techniques, and processes to improve the effectiveness and efficiency of the program.
Track and report program metrics, risk reduction, and security posture improvements, and present results to technical teams and senior leadership.
Provide technical leadership, coaching, and work direction to additional offensive security team members as the team grows.
What We're Looking For:
8+ years of hands-on experience in penetration testing, red teaming, or equivalent offensive security roles.
Demonstrated experience performing penetration tests against cloud environments (Azure, AWS, and/or GCP), endpoints, web and desktop/native applications, and APIs.
Experience conducting full-scope red team operations and purple team exercises.
Strong background in vulnerability triage, risk prioritization, and guiding remediation with development, infrastructure, and security teams.
Experience managing or significantly contributing to a bug bounty program.
Familiarity with continuous attack surface management platforms and external exposure reduction.
Solid understanding of adversary tactics, techniques, and procedures (TTPs) and modern detection and response capabilities.
Excellent written and verbal communication…