Penetration Tester – 6-Month Contract (Hybrid, Toronto)

About the role

Stingrai is seeking a hands‑on Penetration Tester for a six‑month contract with the possibility of a permanent position. The role is hybrid, based in Toronto, and involves both remote work and on‑site client engagements.

Key responsibilities

• Plan and execute penetration tests on web applications, APIs, and internal/external networks.
• Validate and triage findings generated by Stingrai’s AI pentesting agent, Snipe, applying expert judgment.
• Demonstrate real‑world impact by chaining vulnerabilities across cloud services or Active Directory.
• Document findings with clear, prioritized remediation guidance and present reports to technical teams and executives.
• Provide live support to clients through the PTaaS platform during active engagements.
• Stay up‑to‑date with emerging attack techniques, tools, and disclosed vulnerabilities, and share knowledge with the team.
• Contribute to research and development initiatives, security blogs, and community outreach.

Required profile

• Think like an attacker and can prove the impact of identified vulnerabilities.
• Communicate findings clearly and meet deadlines with clients and internal stakeholders.
• Take ownership of deliverables and adapt quickly to varied client environments.
• Commit to continuous learning in the fast‑evolving offensive security field.

Required skills

• OSCP certification (or equivalent).
• Hands‑on experience with web‑application, API, and network penetration testing.
• Familiarity with cloud environments and Active Directory security.