Senior Red Team Operator

Sun Life; London; On-site; CAD 84,000 - 138,000; Full time

Job summary

A leading company in financial services seeks a Senior Red Team Operator to enhance their cybersecurity posture. You'll conduct offensive security assessments, mentor junior operators, and collaborate across teams to identify vulnerabilities. This role offers a competitive salary and flexible work options.

Benefits

Flexible work options

Diversity and inclusion initiatives

Various incentive plans

Qualifications

• 5-7 years’ experience in offensive security or penetration testing.
• Certifications (OSCP, SANS, CEH, CISSP, CPTS) are assets.
• At least 2 years mentoring junior/mid-level operators.

Responsibilities

• Plan and report on Red Team assessments and attack simulations.
• Perform network, web, and mobile application testing.
• Collaborate to develop testing methods for detection capabilities.

Skills

Creative problem-solving

Strong communication

Analytical skills

Education

Degree in computer science

Degree in engineering

Degree in security

Tools

Cobalt Strike

EDR Evasion

AWS

Azure

GCP

Digital Ocean

Job description

Join to apply for the Senior Red Team Operator role at Sun Life

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Join to apply for the Senior Red Team Operator role at Sun Life

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

Job Description:

The primary objectives for the Information Security team are to protect confidential and sensitive information and to maintain operational stability resulting from cyber-attacks. Offensive Security (Red Team) members contribute to these objectives by performing assessments that proactively identify security exposures within the Sun Life environment that go beyond traditional penetration testing. A successful senior red team operator, specializing in offensive security, must possess a diverse set of competencies to effectively simulate cyberattacks and identify vulnerabilities within an organization's systems. Essential skills include a deep understanding of attack vectors and techniques, proficiency in network and application penetration testing, strong analytical skills, effective communication, and adaptability.

What you will do

• Plan, carry out, and report on Red Team assessments, attack simulations, and adversary emulation exercises to identify vulnerabilities.
• Perform network, web, and mobile application testing, source code reviews, threat analysis, and social engineering assessments.
• Develop scripts, tools, and programs for Red Team operations.
• Manage and improve an OPSEC-focused C2 red team cloud environment (AWS, Azure, GCP, Digital Ocean).
• Assist with security control evasion and develop bypass capabilities.
• Collaborate with other teams to develop testing methods for detection capabilities through Purple Team Exercises.
• Research latest threats and adhere to Red Team Framework guidelines.
• Produce weekly/monthly reports on security vulnerabilities and trends.

What you will need to succeed

• 5-7 years’ experience in offensive security or penetration testing.
• Degree in computer science, engineering, or security.
• Experience in offensive security programming and automation languages (C, C++, ASM, C#, JavaScript, PowerShell, Rust, Nim).
• At least 2 years mentoring junior/mid-level operators.
• At least 4 years delivering red team reports and briefings.
• Understanding of security concepts, trends, and practices.
• Creative problem-solving skills.
• High technical knowledge of systems and solutions.
• Certifications (OSCP, SANS, CEH, CISSP, CPTS) are assets.
• Knowledge of OS, network protocols, application configuration, and report writing.
• Strong communication and presentation skills.

Preferred qualifications

• Experience leading grey/black hat engagements.
• Penetration testing experience in network, application, or mobile security.
• Reverse engineering skills (including x86).
• Experience with offensive security tools (Cobalt Strike, EDR Evasion, etc.).
• Proficiency in Active Directory exploitation (On-Prem and Cloud).
• Experience in cybersecurity projects, programming, OSINT, social engineering, and security frameworks like MITRE.
• Knowledge of IaaS and SDN Cloud Environments.
• Proficiency in interpreted (Ruby, Python, PHP) and compiled languages (Java, C, C++, Assembly).
• Knowledge of Windows/Linux/UNIX/OSX internals.

The salary range is from $84,000 to $138,000, depending on location and experience. Sun Life offers various incentive plans, and the company values diversity and inclusion. Accommodation requests can be sent to the provided email. Flexible work options are available. Only shortlisted candidates will be contacted.

Additional Information

Seniority level: Not Applicable

Employment type: Full-time

Job function: Management and Manufacturing

Industry: Financial Services and Insurance

Posting End Date: 23/05/2025