Senior Offensive Engineer & Tooling Lead

Cyber Security Jobs; Michigan; On-site; USD 144,000 - 288,000; Full time

Job summary

CVS Health is seeking a Principal Engineer in Offensive Operations to own and evolve the organization’s offensive tooling ecosystem. This hands‑on leader will contribute to red and purple team engagements while mentoring operators and driving high‑quality technical execution across the program.

The role partners with cross‑functional teams to ensure scalable offensive capabilities aligned with enterprise security priorities, researching emerging threats and technologies to continuously improve

Qualifications

• 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.

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.

Skills

Information Security

Offensive operations

Offensive tooling

Technical leadership

Programming languages

Technical writing

Education

Bachelor's degree

Tools

Python

C/C++

C#

PowerShell

Golang

Job description

CVS Health is seeking a Principal Engineer in Offensive Operations to own and evolve the organization’s offensive tooling ecosystem. This hands‑on leader will contribute to red and purple team engagements while mentoring operators and driving high‑quality technical execution across the program.

The role partners with cross‑functional teams to ensure scalable offensive capabilities aligned with enterprise security priorities, researching emerging threats and technologies to continuously improve