Job Description

Title : Offensive Security Specialist

Job Type: Contract, 12 months

Onsite: 3 days per week

Location: Downtown Toronto

We are seeking a highly skilled Offensive Security Specialist to support our cybersecurity team. This role is deeply technical and focuses on simulating real-world cyberattacks to uncover vulnerabilities across systems, networks, and applications. The ideal candidate brings strong hands-on experience in penetration testing, red team operations, and adversary emulation, with a commitment to staying ahead of emerging threats. You will help strengthen organizational defenses by identifying weaknesses, recommending improvements, and collaborating with cross-functional teams.

Key Responsibilities

Penetration Testing

• Perform ethical hacking engagements across applications, networks, systems, and wireless environments.
• Conduct vulnerability assessments using industry-standard and custom tools.
• Execute both manual and automated testing methodologies (black-box and white-box).
• Assess risk and severity of identified weaknesses.
• Produce clear, detailed reports outlining vulnerabilities, exploitation steps, and recommended remediation.
• Work with technical teams to implement secure practices and address identified issues.

Red / Purple Team Activities

• Lead or support red team exercises simulating sophisticated adversaries and advanced persistent threats.
• Test detection and response capabilities through realistic attack scenarios.
• Conduct social engineering activities such as phishing simulations.
• Execute advanced adversary tactics, including exploitation, lateral movement, privilege escalation, and data exfiltration.
• Participate in or lead tabletop exercises to enhance incident response preparedness.

Collaboration & Reporting

• Partner with IT and security teams to ensure thorough coverage of controls and defenses.
• Provide actionable recommendations to reduce organizational risk.
• Present findings to both technical and non-technical stakeholders in a clear and understandable manner.
• Support knowledge sharing and mentor junior practitioners on offensive security techniques.

Requirements & Qualifications

Technical Requirements

• Proven experience in offensive security or ethical hacking within a corporate or enterprise environment.
• Strong understanding of networking, operating systems (Windows/Linux), web technologies, and cloud architectures.
• Hands-on proficiency with common offensive security, penetration testing, and automation tools.
• Experience identifying and exploiting common vulnerabilities (e.g., OWASP Top 10) and emerging attack vectors.
• Solid knowledge of penetration testing frameworks and methodologies (e.g., PTES, NIST 800-115).
• Experience with cloud attack simulation; exposure to industrial or operational technology (OT/ICS) environments is an asset.
• Familiarity with cybersecurity standards and regulatory frameworks (e.g., NIST, PCI-DSS, GDPR).

Preferred Certifications (Optional)

• OSCP
• CRTP
• GPEN
• CEPT
• GCIH

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