Senior Offensive Security Engineer
DRW is a Chicago-based diversified trading firm that uses technology, quantitative research, and risk management to provide liquidity across traditional and digital-asset markets.
About DRW
Founded by Don Wilson in 1992, DRW trades for its own account across global markets and operates strategies in cryptoassets, venture capital, real estate, carbon markets, and public-equity investments. Its crypto business, Cumberland, has provided institutional crypto-asset liquidity since 2014.
Skills
Candidate Availability
Required and preferred rules are kept separate and reflect the wording in the original posting.
About the Role
You will plan and execute red team engagements, penetration tests, adversary simulations, and social-engineering exercises. You will build offensive tooling, identify and track vulnerabilities, partner on purple-team exercises, assess AI and LLM security, communicate risks, and help mature offensive security practices.
Requirements
- 5+ years of hands-on offensive security, penetration testing, or red teaming experience
- Scripting or programming ability for offensive tooling
- Knowledge of networking, Windows, macOS, Linux, identity providers, and cloud platforms
- Experience with Cobalt Strike, Metasploit, BloodHound, Burp Suite, and Nmap
- Knowledge of MITRE ATT&CK, adversary emulation, detection evasion, and defensive controls
- Clear reporting and communication skills
- Experience with smart contract auditing and blockchain security
- Knowledge of AI and ML security risks, adversarial attacks, prompt injection, and LLM tooling
Responsibilities
- Plan and execute red team engagements and adversary simulations
- Conduct penetration tests across networks, applications, APIs, and cloud infrastructure
- Report findings with actionable remediation guidance
- Build custom tooling, scripts, and exploits to emulate adversary behavior
- Partner in purple-team exercises to improve detection coverage
- Run social-engineering and phishing simulations
- Identify, prioritize, and track vulnerabilities through remediation
- Present engagement results and risk narratives to technical teams and senior leadership
- Assess security risks in AI- and LLM-integrated systems
- Use AI-assisted tooling for reconnaissance, vulnerability discovery, and exploit development
- Define offensive security methodology, standards, and tooling
- Mentor security engineers
Benefits
- Annual discretionary bonus
- Group medical, pharmacy, dental, and vision insurance
- 401k with discretionary employer match
- Short- and long-term disability insurance
- Life and AD&D insurance
- Health savings accounts
- Flexible spending accounts