Staff Offensive Security Engineer

The Red Team team’s mission is to proactively identify and simulate real-world threats against Robinhood’s platforms, properties, and people. Through red teaming and adversarial simulations, the team evaluates security controls, uncovers vulnerabilities, and helps continuously strengthen Robinhood’s overall security posture in close partnership with Detection & Response, Physical Security, and Engineering.

As a Staff Offensive Security Engineer, you will take a hands-on role in designing and executing stealthy adversarial simulations to validate assumptions and uncover gaps in detection and response. You’ll leverage threat modeling, penetration testing, and research-driven techniques to emulate sophisticated attackers, while collaborating cross-functionally to improve defenses and shape more secure systems.

This role is based in our Toronto, Canada office(s), with in-person attendance expected at least 3 days per week.

What you’ll do

• 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.

What you bring

• 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.

Bonus points:

• Experience working in financial technology or regulated environments.
• Prior experience serving as a technical lead on security initiatives.

What we offer

• Challenging, high-impact work to grow your career
• Performance driven compensation with multipliers for outsized impact, bonus programs, and equity ownership
• Top tier benefits to fuel your work, including supplemental health insurance, ancillary insurance, and mental health support programs
• Lifestyle wallet - a highly flexible employer-paid benefits spending account expenses beyond traditional benefits such as wellness, childcare, learning, and more.
• Time off to recharge including company holidays, paid time off, sick time, paid volunteer time off, parental leave, and more!
• Exceptional office experience with catered meals, events, and comfortable workspaces.
• Monthly commuter stipend to help offset in-office commuting costs

Our team is committed to providing an inclusive and welcoming interview experience for all candidates. If you require a specific accommodation during the application or interview process due to a physical or mental condition, please complete this Applicant Accommodation Form to notify our team. The form should only be completed if you need a specific accommodation.

Vacancy Notice: This job posting represents an existing vacancy that we are actively seeking to fill.