As a Staff Offensive Security Engineer at Robinhood, you will play a crucial role in enhancing the security posture of the organization by designing and executing adversarial simulations. You will work within the Red Team to identify vulnerabilities and improve defenses against sophisticated threats. This position requires collaboration with various teams to ensure robust security measures are in place. The role is based in Toronto, Canada, with a strong emphasis on in-person teamwork to foster innovation and community.

• 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) and containerized systems (Docker, Kubernetes).
• Working knowledge of defensive security tools such as IDS/IPS, EDR, and network monitoring.
• Proficiency in Python, Go, or JavaScript for exploit development and automation.
• Clear written and verbal communication skills to explain technical findings to engineers and senior leaders.
• Experience collaborating with distributed teams and documenting work through tools such as Slack, Jira, and GitHub.

• Plan and execute red team operations, adversarial simulations, and penetration tests across various platforms.
• Perform threat modeling for new and existing services, articulating security risks to stakeholders.
• Conduct vulnerability research, exploit development, and testing using custom tooling and public techniques.
• Partner with detection and response teams to simulate realistic attack scenarios.
• Write and maintain tooling to automate and scale offensive security assessments.
• Document findings, recommend remediation strategies, and support teams through fixes.
• Mentor teammates and contribute to shared knowledge through documentation and presentations.