Job Description
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 landscapes—covering SOC, PCI, ISO, HITRUST, and more.
Control Gap, now part of CyberGuard, is Canada’s leading PCI compliance and offensive security consultancy. Together, we deliver one of North America’s most comprehensive cybersecurity and compliance platforms—helping Fortune 50 enterprises, financial institutions, and emerging tech companies safeguard their most critical assets.
About the Role
We’re looking for an experienced Penetration Tester / Offensive Security Consultant to help build and lead our growing Offensive Security practice. You’ll simulate real-world cyberattacks, identify weaknesses before the bad guys do, and help our clients strengthen their defenses.
If you’re passionate about offensive security, thrive in complex technical environments, and want to work alongside some of the brightest minds in cybersecurity—this is your chance to make real impact.
What You’ll 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
You’re curious, analytical, and thrive under pressure
Excellent communication—you 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 innovation—where your work actually matters
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