Role: Offensive Security Engineer
Location: Toronto, ON (4 days onsite/week)
Duration: Fulltime
Responsibilities:
- Lead exploitability assessment and false positive analysis across SAST, DAST, SCA, IAST, container, and infrastructure findings - and translate that analysis into reusable AI agent prompts and skills.
- Identify exploit chains across vulnerability classes that traditional scanners miss and encode the reasoning into agent workflows so the capability scales.
- Validate that AI-generated fixes close exploitable conditions, and feed validation patterns back into agent evaluation frameworks.
- Develop offensive prompts, attack scenarios, and evaluation criteria that the agentic AI capability uses to assess findings autonomously.
- Translate offensive insights into prioritization signals and remediation guidance for VM and engineering teams, delivered through AI-driven workflows.
Requirements:
- 10+ years in offensive security with hands-on exploit development, red teaming, and penetration testing.
- At least one of the following certifications: OSCP, OSCE, OSEP, OSWE, GXPN, or GWAPT.
- Demonstrated ability to identify and validate exploit chains across vulnerability classes.
- Deep fluency in vulnerability classes including memory safety, injection, authentication and authorization flaws, deserialization, race conditions, and supply chain attacks - with real exploitation experience, not just theory.
- Strong code reading skills in at least 3 languages relevant to enterprise stacks (Java, Python, JavaScript, C#, Go), with the ability to pick up new languages quickly enough to assess findings in any production code.
- Hands-on experience with application security testing tools (SAST, DAST, SCA, IAST), specifically around false positive analysis and exploitability validation.
Preferred skills:
- Public evidence of offensive capability: published CVEs, conference talks (DEF CON, Black Hat, OffensiveCon, Recon), CTF placements, bug bounty track record, or open-source offensive tooling contributions.
- Software engineering experience and contributions to production codebases.
- Defensive engineering experience building detection and remediation capabilities.
- Working familiarity with frontier LLMs and agentic AI tools applied to security analysis.
- Modern CI/CD and container platform knowledge (Docker, Kubernetes, GitHub Actions, Jenkins).
- Financial services or regulated industry experience with exposure to SOX, SOC1, and audit.
- Hands-on experience with enterprise vulnerability tooling (Tenable, Aqua, Snyk, BrightSec).
