5 days ago
Responsibilities
- 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 and communicate security risks and tradeoffs to engineering and risk stakeholders.
- Conduct vulnerability research, exploit development, and testing using custom tooling and public proof-of-concept techniques.
- Partner with detection and response teams to simulate realistic attacks and evaluate monitoring and incident response readiness.
- 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 internal documentation, presentations, external talks, or blog posts.
Requirements
- 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 cloud platforms such as AWS and GCP, containerized systems such as Docker and Kubernetes, CI pipelines, and identity systems.
- Working knowledge of IDS/IPS, EDR, packet capture, network monitoring, and common evasion techniques.
- Proficiency in Python, Go, or JavaScript for exploit development, tooling, or automation.
- Clear written and verbal communication skills for explaining technical findings to engineers and senior leaders.
- Experience collaborating with distributed teams and documenting work through Slack, Jira, GitHub, and email.
- Experience in financial technology or regulated environments is preferred.
- Prior experience serving as a technical lead on security initiatives is preferred.
Benefits
- Performance-driven compensation with bonus programs and equity ownership.
- Supplemental health, ancillary insurance, and mental health support programs.
- Flexible employer-paid lifestyle wallet for wellness, childcare, learning, and other expenses.
- Company holidays, paid time off, sick time, paid volunteer time off, and parental leave.
- Catered meals, events, and comfortable workspaces.
- Monthly commuter stipend.
- Based in the Toronto, Canada office with in-person attendance expected at least three days per week.
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