Penetration Testing Analyst

Sun Life; Wellesley (MA); On-site; USD 110,000 - 165,000; Full time

Benefits offered by this job

22 Days Annual Leave

Maternity Leave

Paternity Leave

Parental Leave

Fitness Reimbursement

Annual Bonus plan

Private Health Insurance

Study Assistance Programme

Wellness Programme

Pension Scheme

Professional Development Training

Job summary

Sun Life is seeking a skilled Penetration Testing Analyst to conduct hands-on security testing of applications and infrastructure. The role focuses on penetration testing delivery with secondary exposure to Red Team activities and adversary simulations where needed.

You will perform web, API, mobile, and infrastructure testing, identify vulnerabilities, and provide clear, actionable remediation guidance. A Bachelor's degree in a related field is required; OSCP/ CISSP-like certifications are

Qualifications

• Hands-on web app security testing (OWASP Top 10) and API testing.
• Understanding of authentication, session mgmt, and access control flaws.
• Experience with security testing tools (Burp Suite, Nmap, sqlmap) and manual testing.

Responsibilities

• Perform web, API, mobile, and infrastructure penetration testing across enterprise applications.
• Identify, exploit, and validate security vulnerabilities with manual testing techniques.
• Produce clear, structured reports outlining vulnerabilities, business impact, risk rating, and remediation recommendations.
• Conduct research into new vulnerabilities, exploits, and attack techniques to enhance testing coverage.
• Support Red Team or adversary simulation exercises where required.

Skills

Web application security testing

API security testing

Basic network testing

Authentication flaws

Input validation vulnerabilities

Burp Suite

Nmap

sqlmap

Manual testing

Clear risk articulation

Education

Bachelor's degree in Computer Science or Information Security

Tools

Burp Suite

Nmap

sqlmap

Job description

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.

Key Responsibilities

• 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 behaviour and techniques.

Required Skills & Experience

Core Penetration Testing Skills (Essential)

• Hands‑on 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.

Qualifications

• Bachelor's degree in Computer Science, Information Security, or a related field.
• Certifications such as OSCP, OSWA, CISSP or CompTIA are desired but not required.

Benefits

• 22 Days Annual Leave - increasing to 25 days based on length of service
• Maternity Leave, Paternity Leave, Parental Leave
• C$400/275 Fitness Reimbursement for gym membership annually
• Annual Bonus plan based on Company and Individual Performance
• 100% Private Health Insurance cover for employees and 50% contribution for family members from date of hire
• Study Assistance Programme inclusive of Masters Programme
• S&S Club, Wellness Programme, GP Scheme, Flu Vaccines, Eye Care Scheme as well as lots of discounted events and classes
• Defined Contribution Pension Scheme
• Access to Professional Development Training Platforms