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)