Senior Red Team Operator

Sun Life; Barrie; On-site; CAD 90,000 - 120,000; Full time

Job summary

A leading company in the financial sector is seeking a Senior Red Team Operator to enhance its cybersecurity posture. The role involves conducting offensive security assessments, mentoring junior staff, and developing innovative attack strategies. Ideal candidates will have extensive experience in penetration testing and a strong understanding of security concepts. This position offers a chance to work with advanced security technologies and contribute to the protection of sensitive information.

Qualifications

• 5-7 years’ experience in offensive security / penetration testing.
• Minimum 2 years mentoring junior and mid-level operators.

Responsibilities

• Plan and report on Offensive Security assessments and simulations.
• Perform network and application penetration testing.

Skills

Problem solving

Communication

Analytical skills

Education

University degree in computer science

University degree in computer engineering

University degree in computer security

Tools

Cobalt Strike

EDR Evasion

Malware techniques

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 the realm of 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. Firstly, a deep understanding of various attack vectors and techniques is essential, including knowledge of malware, social engineering, and exploit development. Additionally, proficiency in network and application penetration testing is crucial for identifying weaknesses in infrastructure and software. Strong analytical skills are necessary to assess risks and prioritize targets accurately. Effective communication skills are vital for conveying findings and recommendations to stakeholders. Finally, adaptability and creativity are indispensable traits for devising innovative attack strategies and staying ahead of evolving threats in the cybersecurity landscape.

What you will do?

The essential functions and responsibilities of this position include but are not limited to the following :

• Plan, carry out, and report on Offensive Security (Red Team) assessments, attack simulations and adversary emulation exercises to identify vulnerabilities in critical information systems.
• Perform network penetration, web and mobile application testing, source code reviews, threat analysis, and social engineering assessments.
• Develop scripts, tools, and programs for Red Team operations.
• Manage, maintain, and improve an OPSEC-focused state-of-the-art command-and-control (C2) red team cloud environment (AWS, Azure, GCP ,Digital Ocean)
• Assist with and develop security control evasion and bypass capabilities.
• Work with other parts of the business to develop a method for testing detection capabilities through Purple Team Exercises and Red Team exercises (e.g., IA scenarios, AB scenarios etc.)
• Research latest threats and adhere to guidelines on Red Team Frameworks
• Assist in the production of weekly / monthly reports on security vulnerability trending and direction.

What you will need to succeed?

• 5-7 years’ experience in an offensive security / penetration testing role.
• University degree in computer science, computer engineering or computer security.
• Minimum 2 years mentoring junior and mid-level operators on red team tradecraft
• Minimum 4 years of experience in delivering technical red team reports and briefings
• A general understanding of information security concepts and security trends and practices
• Problem solving with creative solutions.
• Maintain high technical knowledge of systems and solutions.
• Industry certifications (OSCP / SANS / CEH / CISSP, CPTS) are a strong asset.
• Understand operation systems (OS), network protocols, application configuration with excellent report-writing skills.
• Strong communication and presentation skills

Preferred knowledge or qualifications in the following :

• Experience in leading grey / black hat engagements from start to finish.
• Network, Application or Mobile Penetration testing experience.
• Experience in reverse engineering (including x86)
• Offensive Security tooling experience : Cobalt Strike, EDR Evasion, Social Engineering platforms, Malware techniques, Custom tooling, and pipeline development.
• Proficient in Active Directory exploitation (On-Prem and Cloud)
• Related projects in cybersecurity, programming, etc.
• OSINT (Open-source intelligence gathering)
• Social engineering techniques and tactics
• IaaS and SDN Cloud Environments (AWS, Azure, Digital Ocean)