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Robinhood is seeking a Staff Offensive Security Engineer to join its Red Team, a specialized unit focused on proactively identifying and simulating real-world threats against the company's platforms, properties, and people. This is a hands-on, high-impact role where you'll design and execute stealthy adversarial simulations to validate security assumptions, uncover vulnerabilities, and strengthen Robinhood's overall security posture.
You will plan and execute red team operations, adversarial simulations, and penetration tests across applications, infrastructure, networks, offices, and internal processes. Your responsibilities include performing threat modeling for new and existing services, conducting vulnerability research and exploit development, and partnering with detection and response teams to simulate realistic attack scenarios and evaluate incident response readiness. You'll write and maintain tooling to automate and scale offensive security assessments, serve as a subject matter expert by documenting findings and recommending remediation strategies, and mentor teammates while contributing to shared knowledge through internal documentation and external presentations.
You bring 8+ years of hands-on experience in red teaming, offensive security, or penetration testing, with demonstrated experience mentoring other security engineers. You have a strong understanding of threat modeling methodologies and the MITRE ATT&CK framework, and experience testing modern environments including cloud platforms (AWS, GCP), containerized systems (Docker, Kubernetes), CI pipelines, and identity systems. You're proficient in Python, Go, or JavaScript for exploit development and tooling, with working knowledge of defensive security tools such as IDS/IPS, EDR, and network monitoring. Clear communication skills and experience collaborating with distributed teams are essential.
Bonus qualifications include experience in fintech or regulated environments, and prior experience as a technical lead on security initiatives. The role is based in Toronto with in-person attendance expected at least 3 days per week. Robinhood offers competitive compensation with performance-driven bonuses and equity, comprehensive benefits, flexible time off, and an exceptional office experience.
