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Senior Cyber Security Specialist- Offensive Security

Remote / Online - Candidates ideally in
Toronto, Ontario, M5A, Canada
Listing for: Trident Staff
Full Time, Seasonal/Temporary, Remote/Work from Home position
Listed on 2026-07-20
Job specializations:
  • IT/Tech
    Cybersecurity, Security Management & Operations, Information Security
Job Description & How to Apply Below
Job Description

This is a remote position.

Senior Cyber Security Specialist-Offensive Security

Location: Remote (Canada)

Experience: 10+ Years

Employment Type: Full-time / Contract

Job Summary

We are seeking a Senior Cyber Security Specialist (Offensive Security) to lead penetration testing and red team assessments across enterprise applications, APIs, cloud, and modern platforms.

Required Certification (Mandatory)

  • OSCP OR OSEP OR OSCE OR GPEN OR GWAPT
Preferred
  • Cloud security experience (AWS / Azure / GCP)
  • Scripting for automation (Python / Bash / Power Shell)
  • Exposure to Dev Sec Ops  and AI/LLM security testing
Responsibilities
  • Perform advanced penetration testing and red team exercises
  • Identify, validate, and exploit security vulnerabilities
  • Conduct manual security testing across web, API, mobile, and cloud
  • Develop proof-of-concept exploits where required
  • Work with engineering teams on remediation and secure SDLC
  • Provide clear technical risk analysis and reporting
Required Skills
  • 10+ years of hands-on experience in penetration testing, red teaming, or offensive security
  • Strong knowledge of OWASP Top 10, ASVS, WSTG, and NIST 800
  • Experience with Burp Suite, Nmap, Nessus, Metasploit
  • Experience with SAST and DAST testing
  • Exploit development experience in C, C++, Java, or C#
  • Strong Linux/Unix and Windows administration skills
  • Ability to validate findings and reduce false positives
  • Experience with secure SDLC and engineering collaboration

Requirements
cybersecurity
Position Requirements
10+ Years work experience
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