Penetration Tester

2 days ago

Toronto, Canada Control Gap Inc. Full time

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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