Opportunity at
RobinhoodStaff Offensive Security Engineer
Robinhood is seeking a Staff Offensive Security Engineer to join its Red Team in Toronto, Canada. The company operates in the financial technology sector with a…
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About This Role
Robinhood is seeking a Staff Offensive Security Engineer to join its Red Team in Toronto, Canada. The company operates in the financial technology sector with a mission to democratize finance, anticipating significant generational wealth transfer. This position is suited for an experienced security professional with a strong background in adversarial simulations, threat modeling, and penetration testing who thrives in a collaborative, fast-paced environment. As part of the Red Team, the…
Job Description
Robinhood is seeking a Staff Offensive Security Engineer to join its Red Team in Toronto, Canada. The company operates in the financial technology sector with a mission to democratize finance, anticipating significant generational wealth transfer. This position is suited for an experienced security professional with a strong background in adversarial simulations, threat modeling, and penetration testing who thrives in a collaborative, fast-paced environment.
As part of the Red Team, the chosen candidate will actively identify and simulate realistic threats to assess Robinhood's security posture across applications, networks, and physical offices. Responsibilities include designing stealthy attacks, executing penetration tests, researching vulnerabilities, and collaborating closely with engineering and incident response teams. The role requires working on-site in the Toronto office at least three days per week.
Robinhood provides a comprehensive rewards package for this full-time role, including performance-driven compensation with equity and bonus opportunities, supplemental health and mental health insurance, a flexible lifestyle wallet, and various paid time-off options. The expected base pay range for the Toronto location is $191,250 to $225,000 CAD.
Responsibilities
- Plan and conduct red team operations, penetration tests, and adversarial simulations across networks, applications, infrastructure, and internal processes
- Perform threat modeling for new and existing services to communicate security risks and tradeoffs to stakeholders
- Conduct vulnerability research and develop exploits utilizing both public proof-of-concept techniques and custom tooling
- Collaborate with detection and response teams to evaluate monitoring capabilities and incident readiness through realistic attack scenarios
- Write and maintain automated tooling to scale offensive security assessments
- Document findings, recommend remediation strategies, and mentor teammates through knowledge sharing and internal documentation
Requirements
- At least 8 years of hands-on experience in offensive security, red teaming, or penetration testing
- Demonstrated background in guiding or mentoring other security engineers
- Strong knowledge of threat modeling methodologies alongside the MITRE ATT&CK framework
- Experience assessing modern environments such as cloud platforms, containerized systems, CI pipelines, and identity systems
- Working familiarity with defensive security controls, packet capture, EDR, IDS/IPS, and evasion techniques
- Proficiency in JavaScript, Python, or Go for automation, tooling, and exploit development
- Ability to communicate technical findings clearly to engineers and senior leadership
- In-person attendance in the Toronto, Canada office at least 3 days per week
Qualifications
- Experience working within financial technology or other regulated environments
- Prior background serving as a technical lead on security initiatives
Core Skills
Benefits
- Performance driven compensation with bonus programs, equity ownership, and performance multipliers
- Top tier benefits including supplemental health insurance, ancillary insurance, and mental health support programs
- Employer-paid lifestyle wallet for wellness, childcare, learning, and other flexible expenses
- Time off including paid time off, sick leave, company holidays, paid volunteer time off, and parental leave
- Office amenities including catered meals, events, and a monthly commuter stipend
Frequently Asked Questions
What is the location and remote work policy for this role?
This position is based in the Toronto, Canada office, with in-person attendance expected at least three days per week.
What is the expected salary range for the Staff Offensive Security Engineer position?
The expected base pay range for the Toronto location is $191,250 to $225,000 CAD, alongside eligibility for bonus opportunities, equity, and benefits.
What are the primary experience requirements for applicants?
Candidates must have eight or more years of hands-on experience in penetration testing, offensive security, or red teaming, along with a strong understanding of threat modeling and the MITRE ATT&CK framework.
What employment type is this position?
The posting indicates an existing vacancy for a full-time role.
Sample Interview Questions
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