Senior Red Team Operator

About the Role

Join a dynamic team committed to protecting sensitive information and ensuring operational stability against cyber threats at Sun Life. As a Senior Red Team Operator, you will be empowered to utilize your unique background and skills to simulate cyberattacks, identify vulnerabilities beyond standard penetration tests, and contribute actively to maintaining security in our environment. You will collaborate with expert colleagues and leaders who inspire growth and innovation, offering impactful work that benefits individuals, families, and communities worldwide.

Key Responsibilities

• Design, execute, and provide detailed reports on Red Team assessments, adversary emulation, and attack simulations to uncover weaknesses in critical information systems.
• Conduct network, web, and mobile application penetration testing, including source code reviews, threat assessments, and social engineering evaluations.
• Create and maintain scripts, tools, and software to support Red Team operations.
• Administer and enhance an operational security-focused command-and-control cloud environment across platforms such as AWS, Azure, GCP, and Digital Ocean.
• Develop and refine techniques for bypassing security controls and evasion.
• Collaborate cross-functionally to design Purple Team exercises and methodologies for testing detection capabilities.
• Stay updated on the latest threat landscapes and comply with best practices outlined in Red Team Frameworks.
• Prepare regular analytical reports on vulnerability trends and security directions.

Qualifications and Experience

• 5 to 7 years of professional experience in offensive security or penetration testing roles.
• Bachelor’s degree in Computer Science, Computer Engineering, or Computer Security.
• Proficient in offensive security programming and automation languages including C, C++, Assembly, C#, JavaScript, PowerShell, Rust, Nim, among others.
• At least 2 years mentoring junior and mid-level red team members in tradecraft.
• Minimum 4 years delivering technical red team findings and briefings.
• Comprehensive understanding of information security principles, emerging trends, and best practices.
• Creative problem-solving skills coupled with a high technical aptitude.
• Industry certifications such as OSCP, SANS, CEH, CISSP, or CPTS are highly desirable.
• Strong knowledge of operating systems, network protocols, application configurations, and excellent report writing capabilities.
• Effective communication and presentation skills.

Preferred Skills and Knowledge

• Experience leading complex grey/black hat engagements.
• Skilled in network, application, and mobile penetration testing.
• Reverse engineering experience, including x86 architectures.
• Expertise in offensive security tools such as Cobalt Strike, EDR evasion methods, social engineering platforms, malware tactics, custom tools, and pipeline development.
• Proficiency exploiting Active Directory environments (both On-Premises and Cloud).
• Background in cybersecurity projects and programming initiatives.
• Competence in OSINT and social engineering strategies.
• Understanding of defense in depth concepts including the MITRE ATT&CK framework.
• Experience working with IaaS and SDN cloud solutions like AWS, Azure, and Digital Ocean.
• Knowledge of interpreted (Ruby, Python, PHP) and compiled languages (Java, C, C++, Assembly).
• Familiarity with Windows, Linux, UNIX, and OSX internals.

Compensation and Benefits

The salary for this position ranges between €62,200 and €93,300 annually. Final compensation will be based on your skills, experience, education, and qualifications. In addition to the base salary, you may be eligible for an annual discretionary performance incentive. Our workplace emphasizes equity and transparency in pay, recognizing and rewarding individual contributions.