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Zoho

Penetration Testing/ Red Team Engineer

Toronto, ON, Canada

Contract

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Job details

Job type: Contract
Apply by: Dec 4, 2026
Experience: · 3–5 years of experience in Penetration Testing, Red Teaming, Security Engineering, or Software Development with a strong security focus.
Posting language: English
Posted: Nov 4, 2026

Original job description

Senior Penetration Tester

Toronto, ON – Hybrid – 2 Days

Job Summary

We are seeking a Senior Penetration Tester / Red Team Engineer to support offensive security initiatives through advanced penetration testing, red team operations, and custom security tool development. This role combines hands-on security engineering with offensive security expertise to identify vulnerabilities, simulate real-world attack scenarios, and develop automation solutions that enhance security assessment capabilities. The ideal candidate will possess strong software development skills, a deep understanding of security testing methodologies, and experience conducting enterprise security assessments.

*Please note, this role is not able to offer visa transfer or sponsorship now or in the future*

In this role, you will:

· Design and develop custom security tools, automation frameworks, and scripts to support penetration testing and red team operations.

· Conduct comprehensive penetration testing of web applications, APIs, cloud platforms, networks, and enterprise infrastructure.

· Participate in red team engagements that emulate real-world adversaries to evaluate organizational security defenses.

· Identify, validate, and document vulnerabilities, attack paths, and security weaknesses with actionable remediation recommendations.

· Build integrations between security tools, enterprise platforms, and automation workflows to improve testing efficiency and coverage.

· Research and develop offensive security techniques, attack simulations, and proof-of-concept exploits for emerging threats.

· Support security engineering initiatives by solving complex technical challenges requiring both development and cybersecurity expertise.

· Collaborate with development, infrastructure, and security teams to improve security posture and address identified risks.

· Maintain detailed documentation of testing methodologies, findings, tools, and operational procedures.

· Contribute to continuous improvement of penetration testing, red teaming, and security automation capabilities across the organization.

What you need to have to be considered

· 3–5 years of experience in Penetration Testing, Red Teaming, Security Engineering, or Software Development with a strong security focus.

· Strong programming and scripting expertise in languages such as Python, Go, Java, C#, PowerShell, or similar technologies.

· Hands-on experience conducting penetration testing using industry-standard methodologies and frameworks.

· Experience participating in red team engagements and adversary simulation exercises.

· Proficiency with offensive security tools such as Burp Suite, Metasploit, Nmap, Cobalt Strike, BloodHound, or similar platforms.

· Strong understanding of web application security, API security, network security, and cloud security concepts.

· Experience developing custom security tools, automation scripts, or offensive security utilities.

· Familiarity with security frameworks such as MITRE ATT&CK, OWASP Top 10, and penetration testing best practices.

· Excellent analytical, troubleshooting, documentation, and communication skills.

· Security certifications such as OSCP, CRTO, PNPT, GPEN, CEH, or equivalent are highly desirable.

Apply About employer

More about this job

Responsibilities

Develop custom security tools and automation, conduct penetration tests across applications, APIs, cloud platforms, networks, and infrastructure, and participate in red team engagements. Document vulnerabilities and attack paths, recommend remediation, and collaborate with technical teams to improve security capabilities and posture.

Requirements

Requires 3–5 years of relevant experience, strong programming and scripting skills, hands-on penetration testing and red team experience, and familiarity with offensive security tools and frameworks. Certifications such as OSCP, CRTO, PNPT, GPEN, or CEH are highly desirable.

Skills

Penetration Testing
Red Teaming
Security Engineering
Python
Go
Java
C#
PowerShell
Web Application Security
API Security
Cloud Security
Network Security
Security Automation
Vulnerability Assessment
Adversary Simulation
Security Tool Development

Visa sponsorship

Not detected in the job text

Keywords

Penetration Testing
Red Team Operations
Security Engineering
Python
Go
Java
C#
PowerShell
Burp Suite
Metasploit
Nmap
Cobalt Strike
BloodHound
MITRE ATT&CK
OWASP Top 10
Web Application Security
API Security
Cloud Security
Network Security
Enterprise Infrastructure
Security Automation
Custom Security Tools
Adversary Simulation
Vulnerability Assessment
OSCP
CRTO
PNPT
GPEN
CEH

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