Staff Red Team Engineer — Offensive Security

Robinhood; Toronto; On-site; CAD 191,000 - 225,000; Full time

Benefits offered by this job

Equity ownership

Bonuses

Benefits package

Commuter stipend

Job summary

Robinhood in Toronto, Canada seeks a Staff Offensive Security Engineer to design and execute stealthy adversarial simulations, validate assumptions, and uncover gaps in detection and response. You will leverage threat modeling, pentesting, and research-driven techniques to strengthen defenses and build more secure systems.

You will mentor teammates, document findings, and drive remediation with cross-functional partners.

Qualifications

• 8+ years of hands-on experience in red teaming, offensive security, or penetration testing.
• Demonstrated experience mentoring or guiding other security engineers.
• Strong understanding of threat modeling methodologies and the MITRE ATT&CK framework.
• Experience testing modern environments, including cloud platforms (AWS, GCP), containerized systems (Docker, Kubernetes), CI pipelines, and identity systems.
• Working knowledge of defensive security tools such as IDS/IPS, EDR, packet capture, and network monitoring, including common evasion techniques.
• Proficiency in Python, Go, or JavaScript for exploit development, tooling, or automation.
• Clear written and verbal communication skills, with the ability to explain technical findings to both engineers and senior leaders.
• Experience collaborating with distributed teams and documenting work through tools such as Slack, Jira, GitHub, and email.

Responsibilities

• Plan and execute red team operations, adversarial simulations, and penetration tests across applications, infrastructure, networks, offices, and internal processes.
• Perform threat modeling for new and existing services, clearly articulating security risks and tradeoffs to engineering and risk stakeholders.
• Conduct vulnerability research, exploit development, and testing using both custom tooling and public proof-of-concept techniques.
• Partner with detection and response teams to simulate realistic attack scenarios and evaluate monitoring and incident response readiness.
• Write and maintain tooling to automate and scale offensive security assessments.
• Serve as a subject matter expert by documenting findings, recommending remediation strategies, and supporting teams through fixes.
• Mentor teammates and contribute to shared knowledge through internal documentation, presentations, and external talks or blog posts.

Skills

Red teaming

Mentoring

Threat modeling

MITRE ATT&CK

AWS/GCP

Docker/Kubernetes

CI pipelines

Identity systems

Python/Go/JS

Communication

Distributed teams

Documentation tools

Tools

Slack

Jira

GitHub

Email

IDS/IPS

EDR

Packet capture

Network monitoring

Job description

Robinhood in Toronto, Canada seeks a Staff Offensive Security Engineer to design and execute stealthy adversarial simulations, validate assumptions, and uncover gaps in detection and response. You will leverage threat modeling, pentesting, and research-driven techniques to strengthen defenses and build more secure systems.

You will mentor teammates, document findings, and drive remediation with cross-functional partners.