Penetration Testing Analyst

Job Description

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At Sun Life, we work together, share common values, and encourage growth and achievement. We are seeking a skilled Penetration Testing Analyst to perform hands-on security testing of applications, infrastructure, and systems.

This role is primarily focused on Penetration Testing delivery, with secondary exposure to Red Team activities, contributing to adversary simulation exercises where required. The successful candidate will have strong technical testing capabilities, with an interest in developing broader offensive security skills.

What you will do:

• Perform web, API, mobile, and infrastructure penetration testing across enterprise applications.
• Identify, exploit, and validate security vulnerabilities using manual testing techniques and industry tools.
• Conduct testing in line with established methodologies and security frameworks (e.g., OWASP).
• Produce clear, structured reports outlining:Vulnerabilities and root causeBusiness impact and risk ratingPractical remediation recommendations
• Perform research into new vulnerabilities, exploits, and attack techniques to enhance testing coverage.
• Support re-testing activities to validate remediation of identified issues.
• Support Red Team or adversary simulation exercises where required.
• Contribute to reconnaissance and attack surface mapping, Identification of potential attack paths.
• Support documentation of attack paths and identified security gaps.
• Assist in controlled exploitation activities under guidance, including:Initial access techniquesLimited post-exploitation validation (e.g., privilege escalation concepts, lateral movement awareness)
• Collaborate with senior team members to understand real-world attacker behavior and techniques.

What you need to succeed:

• Bachelor’s degree in computer science, Information Security, or a related field.
• Practical PenTesting Certifications such as OSCP, OSWA, CWES & BSCP etc... are desired but not required.

Core Penetration Testing Skills (Essential)

• 2+ years of hands-on professional experience in:Web application security testing (OWASP Top 10)API security testingBasic network/infrastructure testing
• Strong understanding of:Authentication, session management, and access control flawsInput validation and injection vulnerabilities
• Experience with tools such as:Burp Suite, Nmap, sqlmap, or similar
• Ability to perform manual testing beyond automated scanning.
• Strong documentation and reporting skills, with focus on clear risk articulation.

Red Teaming Skills (Desirable – Foundational Level)

• Basic understanding of adversary simulation concepts and attack lifecycle.
• Familiarity with:Reconnaissance techniquesCommon initial compromise methods
• Awareness of:Privilege escalation and lateral movement conceptsAttack paths across enterprise environments
• Interest in developing Red Team and offensive security capabilities over time.

Unique requirement:

Must be able to satisfactorily complete applicable background checks prior to the start date and during employment, in accordance with Sun Life’s policies and practices.

What’s in it for you:

• We’re honoured to be recognized as a 2026 Best Workplaces in Canada by Great Place to Work® Canada.
• Wellness programs that support the three pillars of your health – mental, physical, and financial
• The opportunity to move along a variety of career paths with amazing networking potential.
• As a hybrid organization, you and your leader use business and Client needs to choose where you work, at home or in the office