Lead Offensive Security Engineer - Red Team

CVS Health; Maryland; Hybrid; USD 144,000 - 288,000; Full time

Job summary

CVS Health is seeking a Principal Engineer, Offensive Operations, to own and evolve the organization's offensive tooling ecosystem while leading advanced adversarial operations. The role combines hands-on red/purple team work with mentoring operators and driving scalable, high-quality execution across programs.

You will partner with cross-functional teams to ensure capabilities are aligned to security priorities, with focus on tooling design, automation, and emerging techniques in enterprise and

Qualifications

• 10+ years of information security and/or cybersecurity experience.
• 7+ years in offensive operations and tactics.
• 5+ years building or using offensive tooling in real-world environments.
• 3+ years leading complex technical engagements.
• 3+ years in one or more programming/scripting languages.
• 3+ years in technical writing and post-engagement debriefs.

Responsibilities

• Lead the development, integration, and evolution of offensive tooling and supporting capabilities.
• Establish and promote best practices for tooling design, automation, and technical standards.
• Evaluate and incorporate emerging technologies and techniques into offensive operations.
• Lead or support complex adversary emulation and red team engagements.
• Design and execute advanced testing scenarios across enterprise and cloud environments.
• Ensure high-quality technical execution and repeatable methodologies.
• Act as a senior technical leader and mentor for offensive operators and engineers.
• Provide guidance on tradecraft, tooling usage, and technical problem-solving.
• Contribute to standardised approaches and internal knowledge sharing.
• Partner with security, engineering, and threat intelligence teams to translate offensive findings into defensive improvements.
• Support alignment of offensive capabilities with business and security priorities.
• Research emerging threats, attack techniques, and technologies.
• Contribute to continuous improvement of offensive capabilities and methodologies.

Skills

Offensive ops

Tooling development

Information Security

Leadership

Technical writing

Programming

Cloud security

Education

Bachelor's degree

Equivalent experience

Job description

CVS Health is seeking a Principal Engineer, Offensive Operations, to own and evolve the organization's offensive tooling ecosystem while leading advanced adversarial operations. The role combines hands-on red/purple team work with mentoring operators and driving scalable, high-quality execution across programs.

You will partner with cross-functional teams to ensure capabilities are aligned to security priorities, with focus on tooling design, automation, and emerging techniques in enterprise and