Principal Engineer - Offensive Operations
About The Position
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. Position Summary 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.
Requirements
- 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
- 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)
Nice To Haves
- 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
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 development of standardized 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
Benefits
- medical
- dental
- vision coverage
- paid time off
- retirement savings options
- wellness programs
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What This Job Offers
Job Type
Full-time
Career Level
Principal
