Staff Offensive Security Engineer at Robinhood. About the role Robinhood is seeking a technical expert to join our Red Team and proactively challenge our security infrastructure. You will design and execute adversarial simulations to identify vulnerabilities across our platforms and processes.
Key facts Location: Toronto, Canada
Engagement: Full time, in-office at least 3 days per week
Salary: $191,250 to $225,000 CAD base pay, plus bonus, equity, and benefits
Team: Red Team
What you'll do Plan and carry out red team operations, penetration tests, and adversarial simulations across networks, applications, and physical office environments.
Build threat models for new and existing services to communicate risks to engineering and risk stakeholders.
Research vulnerabilities and develop exploits using custom or public proof-of-concept methods.
Coordinate with detection and response teams to test monitoring readiness and incident response capabilities.
Create and maintain automation tooling to scale security assessments.
Document findings, provide remediation guidance, and mentor team members through technical presentations and internal documentation.
Requirements 8+ years of professional experience in penetration testing, offensive security, or red teaming.
Proven track record of mentoring and guiding other security engineers.
Mastery of threat modeling and the MITRE ATT&CK; framework.




Experience testing cloud environments like AWS and GCP, containerized systems such as Kubernetes and Docker, CI pipelines, and identity systems.
Proficiency in defensive security concepts including EDR, IDS/IPS, network monitoring, and packet capture, along with evasion techniques.
Coding skills in Go, Python, or JavaScript for automation and exploit development.
Strong communication skills for explaining technical risks to both engineering teams and senior leadership.
Experience working with distributed teams using tools like Jira, Slack, GitHub, and email.
Nice to have Experience in fintech or other highly regulated industries.
Background as a technical lead for security projects.
Skills & tools Python, Go, JavaScript
AWS, GCP
Kubernetes, Docker
MITRE ATT&CK;
EDR, IDS/IPS, network monitoring
Jira, GitHub, Slack
Practical notes Compensation includes performance-based multipliers, bonus programs, and equity.
Benefits include supplemental health insurance, mental health support, ancillary insurance, and a lifestyle wallet for wellness and childcare expenses.
The role includes a monthly commuter stipend.
Paid time off includes company holidays, sick leave, volunteer time, and parental leave.
Candidates requiring accommodations for the application or interview process should use the Applicant Accommodation Form.

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📌 Staff Offensive Security Engineer (Ontario)
🏢 Robinhood
📍 Ontario