Penetration Testing Analyst

Location: Toronto, Ontario, Waterloo, Ontario

Time Type: Full time

Job Description

You are as unique as your background, experience and point of view. Here, you’ll be encouraged, empowered and challenged to be your best self. You'll work with dynamic colleagues - experts in their fields - who are eager to share their knowledge with you. Your leaders will inspire and help you reach your potential and soar to new heights. Every day, you'll have new and exciting opportunities to make life brighter for our Clients - who are at the heart of everything we do.

At Sun Life, we're driven by our Purpose: helping our Clients achieve lifetime financial security and live healthier lives. Our values shape how we work: caring, authentic, bold, inspiring, and impactful.

When you join Sun Life, you'll work with passionate colleagues and empowering leaders who support your growth and celebrate your contributions, so you can make a meaningful difference in our Clients' lives.

Discover how you can make a difference in the lives of individuals, families and communities around the world.

Job Description:

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 cause
  • Business impact and risk rating
  • Practical 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 techniques
  • Limited 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 testing
  • Basic network/infrastructure testing
• Strong understanding of:
  • Authentication, session management, and access control flaws
  • Input 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 techniques
  • Common initial compromise methods
• Awareness of:
  • Privilege escalation and lateral movement concepts
  • Attack 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.
• We are thrilled to be recognized by Excellence Canada with their top-level certification, the Canada Order of Excellence for Mental Health at Work®, for prioritizing employee well-being, fostering a positive work culture, and achieving excellence in mental health.
• 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

 

 

The Base Pay range is for the primary location for which the job is posted. It may vary depending on the work location of the successful candidate or other factors. In addition to Base Pay, eligible Sun Life employees participate in various incentive plans, payment under which is discretionary and subject to individual and company performance. Certain sales focused roles have sales incentive plans based on individual or group sales results.

Diversity and inclusion have always been at the core of our values at Sun Life. A diverse workforce with wide perspectives and creative ideas benefits our Clients, the communities where we operate and all of us as colleagues. We welcome applications from qualified individuals from all backgrounds.

Persons with disabilities who need accommodation in the application process, or those needing job postings in an alternative format, may e-mail a request to thebrightside@sunlife.com.

We are proud to be a hybrid organization that offers our employees the choice and flexibility to work from both the office and virtually based on the needs of the business, our Clients and you.

We may use artificial intelligence to support candidate sourcing, screening, interview scheduling.

We thank all applicants for showing an interest in this position. Only those selected for an interview will be contacted.

Salary Range:

70,000/70 000 - 105,000/105 000

Job Category:

IT - Technology Services

Posting End Date:

25/10/2026