Senior Offensive Security Engineer (AI/LLM)

Location: Chicago, United States

Annual base salary: $175,000–$275,000, plus an eligible discretionary annual bonus.

Company

hirify.global is a diversified trading firm using proprietary capital and technology across global financial markets, with additional strategies in real estate, venture capital, and cryptoassets.

What you will do

• Plan and execute red team engagements, penetration tests, and adversary simulations across trading systems, corporate IT, networks, applications, APIs, cloud infrastructure, and AI-integrated systems.
• Build custom tooling, scripts, and exploits to emulate adversary behavior, test security controls, and validate detection coverage.
• Partner with Security Engineering, SOC, infrastructure, platform, and application teams in purple-team exercises and vulnerability remediation.
• Run social engineering and phishing simulations and improve organizational security awareness.
• Assess AI and LLM security risks, including prompt injection, model manipulation, data poisoning, and abuse of agentic workflows.
• Define offensive security methodology, standards, tooling, and roadmap while mentoring other security engineers and presenting risk findings to technical teams and senior leadership.

Requirements

• 5+ years of hands-on experience in offensive security, penetration testing, or red teaming across the full engagement lifecycle.
• Strong scripting or programming ability for building and adapting offensive tooling.
• Solid understanding of networking, Windows, macOS, Linux internals, identity providers, and cloud platforms.
• Experience with tools such as Cobalt Strike, Metasploit, BloodHound, Burp Suite, and Nmap, plus practical MITRE ATT&CK and adversary emulation knowledge.
• Clear technical reporting and communication skills, including translating findings into risk for engineers and executives.
• Experience with smart contract auditing, blockchain security, and AI/ML security risks such as adversarial attacks and prompt injection.

Culture & Benefits

• High-autonomy environment focused on integrity, innovation, curiosity, and challenging consensus.
• Comprehensive medical, pharmacy, dental, and vision insurance.
• 401(k) with discretionary employer match, disability coverage, life and AD&D insurance.
• Health savings and flexible spending accounts.