Senior Application Security Tester & AI Red Team Subject Matter Expert
Evolve SecurityChicago, Illinois, United States • United States
Posted May 12, 2026
Full Time
About the Company
Evolve Security is a cybersecurity services firm headquartered in Chicago, IL, dedicated to improving client security posture through continuous penetration testing, training services, and talent solutions.
Job Description
The Senior Application Security Tester & AI Red Team Subject Matter Expert is a senior-level offensive security role that involves testing AI-enabled applications, large language models, and agentic systems. The role requires expertise in web application and API security, as well as AI red teaming and threat modeling.
Requirements
- 5-8+ years of offensive security experience with a deep concentration in web application and API penetration testing, plus demonstrable hands-on work testing AI/ML systems
- Mastery of web application and API security beyond the OWASP Top 10
- Expertise in AI red teaming and threat modeling
- Strong scripting and small-tool development in Python, with working knowledge of JavaScript / TypeScript, Bash, and PowerShell
- Familiarity with modern AI applications, vector databases, embedding models, retrieval pipelines, and agent frameworks
Benefits
- Healthcare Benefits
- 401(k) Match
- Parental Leave
- Flexible Paid Time Off
