Red Team Operator, Deloitte Global Technology

Deloitte Canada; Toronto; Remote; CAD 85,000 - 156,000; Full time

Job summary

An established industry player is seeking a cybersecurity expert to join their innovative team. In this dynamic role, you will deliver red team campaigns, conduct intelligence gathering, and utilize advanced tools to ensure the security of networks and systems. You will be part of a collaborative environment that fosters professional growth and offers flexible working options. Your contributions will directly impact the company's mission to protect and support clients across various sectors. If you are passionate about cybersecurity and eager to make a difference, this opportunity is perfect for you.

Benefits

Flexible working options

Bonus program

Wellness programs

Professional development opportunities

Qualifications

• 3+ years in cybersecurity focusing on penetration testing and red team operations.
• Experience with tools for covert C2 infrastructure and automation.

Responsibilities

• Perform intelligence gathering and deliver red team campaigns.
• Maintain documentation and assist in managing Red Team Attack Network.

Skills

Penetration Testing

Ethical Hacking

Red Team Operations

Intelligence Gathering

Windows Active Directory

Covert C2 Infrastructure

Automation

Payload Obfuscation Techniques

Education

Bachelor's Degree in Cybersecurity or related field

Tools

Cobalt Strike

Nighthawk C2

Fortra OST

Bloodhound

Impacket

Mimikatz

Kekeo

Rubeus

socat

Windows Sysinternals Suite

Job description

Date: Apr 14, 2025

Job Type: Permanent
Work Model: Remote
Reference code: 129011
Primary Location: Toronto, ON
All Available Locations: Toronto, ON; Burlington, ON; Calgary, AB; Edmonton, AB; Fredericton, NB; Halifax, NS; Kitchener, ON; Moncton, NB; Ottawa, ON; Regina, SK; Saint John, NB; Saskatoon, SK; St. John's, NL; Vancouver, BC; Victoria, BC; Winnipeg, MB

Our Purpose

At Deloitte, our Purpose is to make an impact that matters. We exist to inspire and help our people, organizations, communities, and countries to thrive by building a better future.

By living our Purpose, we will make an impact that matters.

• Have many careers in one Firm.
• Enjoy flexible, proactive, and practical benefits that foster a culture of well-being and connectedness.
• Learn from deep subject matter experts through mentoring and on-the-job coaching.

What will your typical day look like?

• Deliver red team campaigns by:
• Performing intelligence gathering against target networks, people, processes, and technologies.
• Finding creative ways to obtain a foothold in a target network.
• Delivering malware and establishing command and control (C2).
• Moving stealthily within target networks, satisfying the campaign objectives, while staying undetected by the blue teams.
• Establishing persistence and strategically tuning long-haul beacons to maintain long-term footholds where necessary.
• Perform a wide variety of tasks, as needed, to ensure Red Team campaign success.
• Maintaining in-depth documentation and auditing of actions taken during Red Team operations, at all times, for the purposes of deconfliction and non-repudiation.
• Assist in the management of the Red Team Attack Network and the implementation of new tools and techniques to improve the team’s tradecraft.
• Constantly research, test, and develop new tools, techniques, and procedures (TTPs).
• Translate Red Team campaign technical findings into reportable and actionable Red Team results.
• Ensure deliverables meet the quality and timeliness expected of a world-class Red Team.
• Stay abreast of the latest cyber security threats, trends, and attack techniques; continuously improve our testing methodologies and tools.
• Ensure adherence to the Rules of Engagement during every step of the Red Team engagements.

About the team

Deloitte Technology works at the forefront of technology development and processes to support and protect Deloitte around the world.

Enough about us, let’s talk about you

• 3+ years of experience in cybersecurity, with a focus on penetration testing, ethical hacking, or red team operations.
• Experience with conducting intelligence gathering against companies and their associated people, networks, and technologies.
• Experience conducting complex penetration tests and red team exercises against web applications, networks, and endpoint systems.
• Experience with Windows Active Directory and Azure EntraID.
• Experience maintaining and utilizing covert C2 infrastructure in various cloud platforms and environments. Automation experience is a plus!
• Hands-on experience working with tools like Cobalt Strike, Nighthawk C2, Fortra OST, Bloodhound, Impacket, Mimikatz, Kekeo, Rubeus, socat and the Windows Sysinternals suite.
• Experience with modern payload obfuscation techniques.

Preferred:

• Relevant certifications such as OSCP, OSEP, OSED, OSEE, CRTP, CRTE, etc.
• Public examples of blogs, conference talks, and open-source tooling demonstrating your expertise.
• Experience operating against security products such as Microsoft Defender for Endpoint/Identity and CrowdStrike Falcon.
• Experience with Social Engineering (physical, phishing).
• Experience with Outflank OST.
• Experience automating infrastructure deployment with Ansible and Terraform.
• Experience with fully remote positions.

Total Rewards

The salary range for this position is $85,000 - $156,000, and individuals may be eligible to participate in our bonus program. Deloitte is fair and competitive when it comes to the salaries of our people.

Our Total Rewards Package extends well beyond traditional compensation and benefit programs and is designed to recognize employee contributions, encourage personal wellness, and support firm growth.

Our promise to our people: Deloitte is where potential comes to life.

Be yourself, and more.

Diverse perspectives and life experiences make us better. We provide flexible working options to support you and how you can contribute.

Be the leader you want to be

Some guide teams, some change culture, some build essential expertise. We offer opportunities and experiences that support your continuing growth as a leader.

The next step is yours

Deloitte encourages applications from all qualified candidates who represent the full diversity of communities across Canada.

By applying to this job you will be assessed against the Deloitte Global Talent Standards.