Senior Red Team Operator

About the Role

Join Sun Life's Information Security team where your unique background and expertise will be valued and challenged. You will collaborate with seasoned professionals eager to share their insights, guided by leaders who motivate you to grow and achieve your fullest potential. At Sun Life, our mission is to help clients secure their financial futures and enhance their health, underpinned by core values of care, authenticity, boldness, inspiration, and impact. As part of this mission, your contributions directly support the protection of sensitive information and preserving operational stability against cyber threats.

Job Overview

As a Senior Red Team Operator specializing in offensive security, your role will involve conducting advanced attack simulations and vulnerability assessments that extend beyond typical penetration testing. This position demands a comprehensive skill set including mastery of attack vectors, malware, social engineering, exploit development, and penetration techniques targeting networks and applications. Analytical acumen is key for prioritizing risks, while strong communication is essential for sharing results and recommendations. Creativity and adaptability enable you to craft innovative strategies that keep pace with evolving cybersecurity challenges.

Key Responsibilities

• Design, execute, and document Red Team operations, including attack simulations and adversary emulation, to uncover security weaknesses in critical systems.
• Conduct network, web, and mobile application penetration tests, perform source code reviews, threat analysis, and social engineering assessments.
• Create and maintain scripts, tools, and software to support Red Team initiatives.
• Oversee and enhance an operational security (OPSEC) focused command-and-control (C2) cloud environment using platforms like AWS, Azure, Google Cloud Platform, and Digital Ocean.
• Develop and implement techniques for evading and bypassing security controls.
• Collaborate cross-functionally to establish and refine testing methodologies for detection capabilities, executed through Purple Team and Red Team exercises simulating various adversary scenarios.
• Stay up to date with emerging threats and best practices concerning Red Team frameworks.
• Contribute to the generation of regular reports summarizing security vulnerabilities and threat trends.

Qualifications and Experience

• Between 5 and 7 years of hands-on experience in offensive security or penetration testing roles.
• A university degree in computer science, computer engineering, or computer security.
• Proven expertise in offensive security programming and automation with languages such as C, C++, Assembly, C#, JavaScript, PowerShell, Rust, and Nim.
• At least 2 years of mentoring junior and mid-level Red Team operators.
• Minimum of 4 years producing detailed technical Red Team reports and delivering briefings.
• Solid grasp of information security principles, industry trends, and best practices.
• Strong problem-solving skills with innovative approaches.
• Continued commitment to maintaining current technical knowledge of relevant systems and technologies.
• Industry certifications such as OSCP, SANS, CEH, CISSP, or CPTS are highly regarded.
• Understanding of operating systems, network protocols, and application configurations coupled with excellent report-writing abilities.
• Exceptional communication and presentation skills.

Preferred Skills and Expertise

• Experience leading complex grey and black hat engagements.
• Proficient in network, application, and mobile penetration testing.
• Expertise in reverse engineering, including familiarity with x86 architecture.
• Hands-on experience with offensive security tools like Cobalt Strike, endpoint detection and response evasion, social engineering platforms, malware methods, custom tool development, and automation pipelines.
• Deep knowledge of Active Directory exploitation in both on-premise and cloud environments.
• Experience with cybersecurity and programming projects.
• Open-source intelligence (OSINT) gathering skills.
• Understanding of social engineering tactics.
• Comprehensive defense-in-depth security knowledge, including the MITRE framework.
• Familiarity with Infrastructure as a Service (IaaS) and software-defined networking cloud environments (AWS, Azure, Digital Ocean).
• Programming skills in interpreted languages like Ruby, Python, and PHP.
• Competence in compiled languages including Java, C, C++, and Assembly.
• In-depth knowledge of Windows, Linux, UNIX, and OSX operating system internals.

Additional Details

The annual salary range for this position is between 62,200 and 93,300 EUR, depending on experience. This role is categorized under IT - Technology Services. The application deadline is 27/09/2026.