Senior Tooling Engineer Jobs in Iowa (NOW HIRING)

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.

• 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

• 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:

$144,200.00 - $288,400.00

This pay range represents the base hourly rate or base annual full‑time salary for all positions in the job grade within which this position falls. The actual base salary offer will depend on a variety of factors including experience, education, geography and other relevant factors. This position is eligible for a CVS Health bonus, commission or short-term incentive program in addition to the base pay range listed above. This position also includes an award target in the company's equity award program.

Our people fuel our future. Our teams reflect the customers, patients, members and communities we serve and we are committed to fostering a workplace where every colleague feels valued and that they belong.

We take pride in offering a comprehensive and competitive mix of pay and benefits that reflects our commitment to our colleagues and their families.

This full‑time position is eligible for a comprehensive benefits package designed to support the physical, emotional, and financial well‑being of colleagues and their families. The benefits for this position include medical, dental, and vision coverage, paid time off, retirement savings options, wellness programs, and other resources, based on eligibility.

Additional details about available benefits are provided during the application process and on Benefits Moments.

We anticipate the application window for this opening will close on: 09/07/2026

Qualified applicants with arrest or conviction records will be considered for employment in accordance with all federal, state and local laws.