Senior Red Team Operator, Deloitte Global Technology (Toronto, ON, CA, M5C 3G7)

--

Deloitte Global is the engine of the Deloitte network. Our professionals reach across disciplines and borders to develop and lead global initiatives. We deliver strategic programs and services that unite our organization.

What will your typical day look like?

• Perform intelligence gathering against target networks, people, processes, and technologies.
• Find creative ways to obtain a foothold in a target network.
• Deliver malware and establishing command and control (C2).
• Move stealthily within target networks, satisfying the campaign objectives, while staying undetected by the blue teams.
• Establish 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. In this truly global environment, we operate not in "what is" but rather "what can be" to help Deloitte deliver and connect with its clients, its communities, and one another in ways not previously conceived.

Enough about us, let’s talk about you

• Prior experience leading Red Team engagements or managing offensive security programs.
• 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.
• 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.
• Scripting experience
• Create detail reports and deliver executive-level presentations on findings and recommendations.

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.
• Good communication with executives and team members
• Mentorship and being able to help mentor the team
• Automation experience

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. We regularly benchmark across a variety of positions, industries, sectors, targets, and levels. Our approach is grounded on recognizing people's unique strengths and contributions and rewarding the value that they deliver.

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. Along with a competitive base salary and variable pay opportunities, we offer a wide array of initiatives that differentiate us as a people-first organization. On top of our regular paid vacation days, some examples include: $4,000 per year for mental health support benefits, a $1,300 flexible benefit spending account, firm-wide closures known as "Deloitte Days", dedicated days of for learning (known as Development and Innovation Days), flexible work arrangements and a hybrid work structure.