Job Title

Overview Penetration Tester / Offensive Security Consultant Remote (Canada). Toronto, Ontario, CA preferred. Company: Control Gap, a CyberGuard Advantage company. About Us CyberGuard Advantage is a modern cybersecurity compliance and risk advisory firm backed by Atlantic Street Capital. We help organizations navigate complex privacy, compliance, and security landscapescovering SOC, PCI, ISO, HITRUST, and more. Control Gap, now part of CyberGuard, is Canadas leading PCI compliance and offensive security consultancy. Together, we deliver one of North Americas most comprehensive cybersecurity and compliance platformshelping Fortune 50 enterprises, financial institutions, and emerging tech companies safeguard their most critical assets. About the Role Were looking for an experienced Penetration Tester / Offensive Security Consultant to help build and lead our growing Offensive Security practice. Youll simulate real-world cyberattacks, identify weaknesses before the bad guys do, and help our clients strengthen their defenses. If youre passionate about offensive security, thrive in complex technical environments, and want to work alongside some of the brightest minds in cybersecuritythis is your chance to make real impact. What Youll Do Conduct full-scope penetration testing on networks, applications, cloud environments, and APIs Simulate advanced adversary techniques to evaluate enterprise security posture Deliver detailed technical and executive reports that tell the story behind your findings Mentor and coach junior security testers and ethical hackers Collaborate directly with clients, helping them understand vulnerabilities and prioritize remediation Research and develop new testing methodologies, scripts, and tools for emerging technologies Partner with sales teams on scoping, pre-sales demos, and client workshops Occasionally travel to client sites across Canada for testing and assessments What You Bring 3+ years in penetration testing or red teaming (network, web app, or mobile) 5+ years in IT or Information Security overall Deep knowledge of OWASP Top 10, vulnerability exploitation, and post-exploitation techniques Experience with tools like Burp Suite, Metasploit, Cobalt Strike, Nmap, Wireshark, and custom scripts Familiarity with cloud environments (AWS, Azure, GCP) and secure configuration assessments Understanding of encryption, malware analysis, pivoting, or exploit development is a plus Certifications such as OSCP, OSCE, GXPN, PNPT, GWAPT, or GMOB are highly valued Soft Skills That Set You Apart Youre curious, analytical, and thrive under pressure Excellent communicationyou can explain technical exploits to execs and engineers alike Organized, dependable, and passionate about helping clients stay one step ahead Why Join Us Competitive salary + 4 weeks paid vacation Company-paid medical, dental, and wellness benefits RRSP sharing, paid certifications, and ongoing professional development Fully remote flexibility with team events throughout the year A culture that values expertise, integrity, and innovationwhere your work actually matters #J-18808-Ljbffr