Principal Engineer - Offensive Operations

We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time.

The Principal Engineer is a senior technical leader within Offensive Operations, responsible for owning and evolving the organization’s offensive tooling ecosystem while leading advanced adversarial operations.

This role operates as a hands-on player/coach, contributing directly to complex red and purple team engagements while mentoring operators and driving consistent, high-quality technical execution across the program.

The Principal Engineer partners closely with cross-functional teams to ensure offensive capabilities are scalable, effective, and aligned to enterprise security priorities.

Primary Responsibilities:

Offensive Tooling & Engineering

• 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

Operational Leadership

• 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

Technical Leadership & Mentorship

• 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 development of standardized approaches and internal knowledge sharing

Cross-Functional Collaboration

• 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 & Innovation

• Research emerging threats, attack techniques, and technologies
• Contribute to continuous improvement of offensive capabilities and methodologies

• 10+ years of experience in Information Security and/or Cybersecurity
• 7+ years of direct experience in offensive operations and tactics
• 5+ years of experience building or utilizing offensive tooling in real-world environments
• 3+ years of experience leading complex technical engagements
• 3+ years of experience in one or more programming/scripting languages (e.g., Python, C/C++, C#, PowerShell, Golang)
• 3+ years in technical writing and post-engagement debriefs

• Deep understanding of enterprise environments, identity systems, and cloud platforms
• Experience in Red Team or Purple Team environments
• Familiarity with modern enterprise architectures, cloud platforms, and SaaS environments
• Experience mentoring or leading technical teams
• OSCP, OSWP, CRTP, OSEP, CRTO, GXPN, CISSP or other related industry certifications

• Bachelor’s degree from an accredited college or university, or equivalent combination of education and relevant work experience (High School Diploma/GED plus 4 years of related experience)

The typical pay range for this role is: