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Zoho

Red Team Engineer AND Senior Penetration Tester

Toronto, ON, Canada

Contract

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Job details

Job type: Contract
Apply by: Nov 26, 2026
Experience: · 8+ years of hands-on experience in Penetration Testing, Red Teaming, Offensive Security, or Security Engineering.
Posting language: English
Posted: Oct 27, 2026

Original job description

Client need below:

DAST / Web Application Security: Demonstrated hands-on experience
SAST: Limited/no hands-on experience
SCA: Limited/no hands-on experience
Cloud Security Testing: Limited/no hands-on experience
Mobile Application Security Testing: Limited/no hands-on experience
Threat Research / Emerging Threats: No relevant hands-on experience demonstrated

Senior Penetration Tester / Red Team Engineer

Toronto – Hybrid

Job Summary

We are seeking an experienced Senior Penetration Tester / Red Team Engineer to conduct advanced offensive security assessments across applications, networks, infrastructure, cloud, APIs, and endpoint environments. This role will simulate real-world cyberattacks to identify exploitable weaknesses, validate security controls, and improve enterprise cyber resilience. The ideal candidate will bring deep expertise in penetration testing, exploitation, security automation, and vulnerability analysis. The position requires strong hands-on technical skills combined with the ability to clearly communicate security risks and remediation recommendations.

In this role, you will:

· Conduct comprehensive penetration testing across web applications, APIs, networks, cloud environments, mobile applications, and Windows/Linux systems.

· Perform vulnerability assessments using automated scanning platforms and advanced manual testing techniques to identify exploitable security weaknesses.

· Simulate realistic adversary scenarios to evaluate authentication, authorization, access controls, network defenses, and overall security resilience.

· Identify and validate vulnerabilities, misconfigurations, exposed credentials, insecure code, and potential attack paths across enterprise environments.

· Utilize offensive security tools such as Burp Suite, Metasploit, Nmap, Kali Linux, Pentera, and vulnerability scanning platforms.

· Develop Python and Bash scripts, automation utilities, and custom testing approaches to improve penetration testing efficiency and coverage.

· Document assessment methodologies, technical evidence, risk impact, and findings while providing clear remediation recommendations to stakeholders.

· Partner with application, infrastructure, cloud, and security teams to remediate identified vulnerabilities and validate fixes through retesting.

· Research emerging threats, CVEs, OWASP vulnerabilities, exploitation techniques, and evolving offensive security methodologies.

· Support security assessments, compliance initiatives, risk reviews, and continuous improvement of enterprise offensive security capabilities.

What you need to have to be considered

· 8+ years of hands-on experience in Penetration Testing, Red Teaming, Offensive Security, or Security Engineering.

· Expert-level experience conducting penetration tests across web applications, networks, APIs, endpoints, cloud platforms, and enterprise infrastructure.

· Strong expertise in vulnerability exploitation, attack-path analysis, credential security, authentication testing, and security control validation.

· Advanced hands-on experience with offensive security tools such as Burp Suite, Metasploit, Nmap, Kali Linux, Pentera Console/Surface, and vulnerability scanners.

· Strong scripting and automation skills using Python, Bash, PowerShell, or similar technologies.

· Deep understanding of OWASP, CVE/CVSS, MITRE ATT&CK, network security, application security, and modern attack methodologies.

· Experience working with development and infrastructure teams to provide remediation guidance and perform validation/retesting of security fixes.

· Strong technical reporting skills with the ability to communicate vulnerabilities, business impact, and remediation priorities to technical and leadership audiences.

· Relevant certifications such as OSCP, OSEP, OSWE, GPEN, GXPN, CRTO, or equivalent offensive security certifications are preferred.

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More about this job

Responsibilities

Conduct advanced penetration tests and realistic adversary simulations across applications, APIs, networks, cloud environments, and endpoints to identify and validate exploitable weaknesses. Document risks and remediation guidance, automate testing where useful, collaborate with technical teams to validate fixes, and support security and compliance initiatives.

Requirements

Requires 8 or more years of hands-on experience in penetration testing, red teaming, offensive security, or security engineering, with advanced expertise across enterprise environments and vulnerability exploitation. Candidates should have strong scripting, offensive security tool, security reporting, and remediation collaboration skills; relevant offensive security certifications are preferred.

Skills

Penetration Testing
Red Teaming
Web Application Security
Vulnerability Exploitation
Attack-Path Analysis
API Security Testing
Cloud Security Testing
Network Security Testing
Endpoint Security Testing
Vulnerability Assessment
Security Automation
Python
Bash
PowerShell
Security Reporting
Remediation Validation

Visa sponsorship

Not detected in the job text

Keywords

Penetration Testing
Red Teaming
Offensive Security
Web Application Security
DAST
SAST
SCA
Cloud Security
Mobile Application Security
API Security
Vulnerability Exploitation
Attack-Path Analysis
Burp Suite
Metasploit
Nmap
Kali Linux
Pentera
Python
Bash
PowerShell
OWASP
CVE
CVSS
MITRE ATT&CK
Credential Security
Authentication Testing
Vulnerability Scanners
OSCP
OSEP
OSWE

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