Senior Offensive Security Engineer

Description

The company is a diversified trading firm with over 3 decades of experience. It trades with its own capital and takes its own risk, and it values autonomy and the ability to move quickly on opportunities.

Headquartered in Chicago, with offices in the U.S., Canada, Europe, and Asia, the company trades Fixed Income, ETFs, Equities, FX, Commodities, and Energy in major global markets. It also runs three non-traditional strategies: real estate, venture capital, and cryptoassets.

The company is building out its offensive security capability and is hiring a Senior Offensive Security Engineer to lead it. You will test the trading infrastructure, corporate environment, and cloud platforms by thinking like an attacker, and you will help the firm find and fix weaknesses before outsiders do.

You will work with the security, infrastructure, and trading teams to turn findings into real fixes. You will also help shape the methodology, tooling, and roadmap for offensive security as the function grows.

Responsibilities

• Plan and run red team engagements and adversary simulations against trading systems, corporate IT, and cloud environments, modeling realistic attacker TTPs mapped to frameworks such as MITRE ATT&CK.
• Carry out penetration tests on networks, web and internal applications, APIs, and cloud infrastructure, then report findings with clear remediation steps.
• Build custom tools, scripts, and exploits to mimic adversary behavior, test control effectiveness, and confirm detection coverage.
• Work with the Security Engineering and SOC teams in purple-team exercises to shrink the gap between what attackers can do and what defenders can see.
• Run social engineering and phishing simulations to measure and raise security awareness across the organization.
• Find, validate, rank, and track vulnerabilities and control gaps until they are fixed, working with infrastructure, platform, and application owners.
• Explain engagement results and risk to technical staff and senior leaders in a way that prompts action.
• Track the threat landscape, new TTPs, and offensive tools, and apply what you learn to the firm's defenses.
• Assess AI and LLM-integrated systems for prompt injection, model manipulation, data poisoning, and misuse of agentic workflows, and help the teams building them fix what you find.
• Use AI-assisted tools to speed up reconnaissance, vulnerability discovery, and exploit development, and test new AI-driven offensive techniques as they appear.
• Help define and mature the offensive security methodology, standards, and tooling, and mentor other members of the security team.

Requirements

• 5+ years of hands-on work in offensive security, penetration testing, or red teaming, covering the full engagement lifecycle: reconnaissance, initial access, privilege escalation, lateral movement, persistence, and exfiltration.
• Strong scripting or programming skills to build and adapt offensive tools.
• Solid grasp of networking, Windows, macOS, and Linux internals, identity providers, and cloud platforms.
• Hands-on use of common offensive tools such as Cobalt Strike, Metasploit, BloodHound, Burp Suite, and Nmap, and a record of writing your own tools when needed.
• Working knowledge of MITRE ATT&CK, adversary emulation, and detection evasion, plus enough understanding of defensive controls to help defenders improve.
• A record of clear, precise reporting, and the ability to turn technical findings into risk that engineers and executives both understand.
• Experience with smart contract auditing and blockchain security.
• Familiarity with AI and ML security risks, including adversarial attacks on models, prompt injection, and the offensive and defensive effects of LLM-powered tools.
• A collaborative approach that sees red teaming as a way to make the whole organization more secure, not just a way to find flaws.

Conditions

The annual base salary range is $175,000 to $275,000, set by experience, qualifications, and relevant skill set.

The role is eligible for an annual discretionary bonus.

Benefits

• Group medical, pharmacy, dental, and vision insurance.
• 401k with a discretionary employer match.
• Short-term and long-term disability insurance.
• Life and AD&D insurance.
• Health savings accounts and flexible spending accounts.