Senior Offensive Security Engineer & Tooling Lead

Cyber Security Jobs; South Dakota; 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 while leading advanced adversarial operations. This hands-on leader will mentor operators and drive high‑quality execution across the program.

This role partners with cross‑functional teams to ensure capabilities are scalable, effective, and aligned to enterprise security priorities, with a focus on red team engagements and innovative tooling strategies.

Qualifications

• 10+ years in Information Security and/or Cybersecurity.
• 7+ years in offensive operations and tactics.
• 5+ years building or utilizing offensive tooling in real-world environments.
• 3+ years leading complex technical engagements.
• 3+ years 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 development and evolution of offensive tooling and 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

Programming: Python / C / C++ / Power

Education

Bachelor's degree

Tools

Python

PowerShell

C/C++

C#

Golang

Job description

CVS Health is seeking a Principal Engineer in Offensive Operations to own and evolve the organization\'s offensive tooling ecosystem while leading advanced adversarial operations. This hands-on leader will mentor operators and drive high‑quality execution across the program.

This role partners with cross‑functional teams to ensure capabilities are scalable, effective, and aligned to enterprise security priorities, with a focus on red team engagements and innovative tooling strategies.