14 offensive security jobs at 12 companies in Chicago, IL
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Lead, Offensive Security
Louisville or New York City or Dallas or Charlotte or Tampa or Miami or Washington or Chicago or Boston or Atlanta or Nashville
$142k-$196k/yrRemoteFull Time
HumanaNYSE: HUM: Provides health insurance plans and clinical healthcare services.
6+ YOE6+ Mgmt6+ years in red team/penetration testing with leadership experience; production Python engineering; built or operated agentic AI/LLM applications; experience attacking AI/ML systems; production cloud experience (AWS, GCP, or Azure).
Python, PyRIT, Garak, MITRE ATLAS, OWASP Top 10 for LLM Applications, NIST AI Risk Management Framework, AWS, GCP, Azure, Hack The Box Pro Labs
Horizon3.ai: Autonomous penetration testing platform for continuous security assessment.
Extensive hands-on web application penetration testing experience, ability to reproduce and validate edge-case exploits, strong communication, proxy tool experience (Burp Suite), scripting (Python), and history of security research or bug bounty contributions.
Coinflow: Enables instant global payments using stablecoins and blockchain technology.
4+ YOE4+ years in security engineering or DevSecOps; hands-on offensive and defensive security; SIEM; code experience in TS/Node; vulnerability management; AI-native tooling.
Datadog, Splunk, Elastic, Panther, TypeScript, Node.js, Rust, Go, Python, Claude Security, Claude Code, SAST, DAST, CI/CD
CboeBATS: CBOE: Operates global market infrastructure and provides tradable financial products.
5+ YOE5+ years red teaming or offensive security; bachelor’s degree or equivalent; strong attacker tradecraft; hands-on in endpoint, identity, cloud; knowledge of EDR, SIEM; purple team; communications.
8+ YOEBachelor's degree or equivalent, minimum 8 years information security experience focused on penetration testing, expertise with offensive techniques, cloud/app security, scripting, and at least one offensive security certification.
Alliant Credit Union: Provides digital banking, consumer loans, and mortgage lending services.
3+ YOEBachelor's in CS/related or 6 years' equivalent; minimum 3 years penetration testing/offensive security; preferred offensive security certifications; strong communication and reporting skills.
Minneapolis or Atlanta or Cincinnati or Cupertino or Portland or New York or Chicago or Englewood or Charlotte or Irving
$133k-$157k/yrHybridFull Time
U.S. BankNYSE: USB: Provider of personal, business, and institutional financial services.
8+ YOEBachelor's degree or equivalent, 8+ years in information security with offensive security/Red Team experience; expertise in exploit development, offensive tooling, and scripting; strong communication and leadership.
Horizon3.ai: Autonomous penetration testing platform for continuous security assessment.
10+ YOE10+ years engineering or offensive security experience, hands-on OCI offensive security experience, strong cloud attack path knowledge, Python coding, web and cloud pentesting experience, strong research and documentation skills.
Johnston or Boston or Iselin or Pittsburgh or Cleveland or Chicago or Philadelphia or Manchester
$120k-$210k/yrHybridFull Time
Citizens Financial GroupNYSE: CFG: Provides retail, commercial, and private banking services to customers.
4+ YOE4+ years hands-on offensive security experience with red/purple team operations, adversary emulation, campaign-based testing; Bachelor's preferred or equivalent experience; OSCP/OSEP/CRTO/CRTP or similar; AI security exposure; strong communication.
8+ YOEBachelor's or equivalent, 8+ years in information security with penetration testing focus; hands-on with Burp Suite, Nessus, Metasploit, Nmap; scripting (Bash, Python, Go, PowerShell, JavaScript); offensive cert (OSCP or similar).
Aikido Security: Developer-first security platform for code, cloud, and runtime.
Strong infrastructure and networking fundamentals (Docker, DNS, TLS), Linux debugging, ability to read Go/TypeScript/Python, familiarity with enterprise networks, basic offensive security knowledge, strong communication; must live in Chicago.