Senior Red Team Operator, Deloitte Global Technology

Posting Start Date: 6/1/26

Job Type: PermanentWork Model: RemoteReference code: 131662Primary Location: Toronto, ONAll 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. Our work underpins a prosperous society where people can find meaning and opportunity. It builds consumer and business confidence, empowers organizations to find imaginative ways of deploying capital, enables fair, trusted, and functioning social and economic institutions, and allows our friends, families, and communities to enjoy the quality of life that comes with a sustainable future. And as the largest 100% Canadian-owned and operated professional services firm in our country, we are proud to work alongside our clients to make a positive impact for all Canadians.

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

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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?

Work you'll do

Leading a small team of Red Team Operators in the planning, execution, and reporting of Red Team engagements around the globe. This includes, but is not limited to: 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. Ensuring adherence to the Rules of Engagement during every step of the Red Team engagements. Maintaining operational oversite of all actions conducted during Red Team engagements. Ensuring that every action is planned, executed, and logged properly at all times by every operator. Maintaining in-depth documentation and auditing of actions taken during Red Team operations, at all times, for the purposes of deconfliction and non-repudiation. Identifying and acting on opportunities to train and mentor other members of the Red Team. Assisting in the management of the Red Team Attack Network and the implementation of new tools and techniques to improve the team’s tradecraft. Sharing your research within the Deloitte Global Red Team community, and with the broader security organization, by writing blogs, speaking at conferences, or publishing code. Developing operational processes, field manuals, and attack methodologies to continuously improve the quality of engagements and knowledge sharing amongst the team. Ensure deliverables meet the quality and timeliness expected of a world-class Red Team. Working closely with a wide variety of Deloitte’s industry leading information security teams to identify and reduce risk around the globe. 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

Required:

3+ years of Red Team experience. A deep understanding of threat actor tactics, techniques, and procedures (TTPs). Experience with, and a deep understanding of, digital forensics and incident response capabilities and procedures. Experience with leading Red Team Operations against companies and their associated people, processes, and technologies. The ability to create, update, and maintain documentation ranging from Red Team TTPs to governing documentation as needed. Experience with enumerating and attacking Windows Active Directory and Azure EntraID environments. Experience leading the designing, building, maintaining, and utilization of covert C2 infrastructure in various cloud platforms and environments. Automation experience is a plus! Experience with modern malware development and obfuscation techniques. A deep understanding of enterprise security architecture and the associated security controls. A deep understanding of monitoring, detections, and indicators of compromise/attack, and the implications they have on covert Red Team Operations. Hands on experience working with industry leading Red Team tools like Cobalt Strike, Nighthawk C2, Bloodhound, Evilginx2, etc...

Preferred:

Relevant certifications such as OSCP, OSCE, 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 leading red teaming efforts. 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. 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.

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

Be yourself, and more.

We are a group of talented people who want to learn, gain experience, and develop skills. Wherever you are in your career, we want you to advance.

You Shape How We Make Impact.

Diverse perspectives and life experiences make us better. Whoever you are and wherever you’re from, we want you to feel like you belong here. 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.

Have as many careers as you want.

We are uniquely able to offer you new challenges and roles – and prepare you for them. We bring together people with unique experiences and talents, and we are the place to develop a lasting network of friends, peers, and mentors.

The next step is yours

At Deloitte, we are all about doing business inclusively – that starts with having diverse colleagues of all abilities. Deloitte encourages applications from all qualified candidates who represent the full diversity of communities across Canada. This includes, but is not limited to, people with disabilities, candidates from Indigenous communities, and candidates from the Black community in support of living our values, creating a culture of Diversity Equity and Inclusion and our commitment to our AccessAbility Action Plan, Reconciliation Action Plan and the BlackNorth Initiative.

We encourage you to connect with us at accessiblecareers@deloitte.ca if you require an accommodation for the recruitment process (including alternate formats of materials, accessible meeting rooms or other accommodations) or indigenouscareers@deloitte.ca for any questions relating to careers for Indigenous peoples at Deloitte (First Nations, Inuit, Métis).

By applying to this job you will be assessed against the Deloitte Global Talent Standards. We’ve designed these standards to provide our clients with a consistent and exceptional Deloitte experience globally.

Deloitte Canada has 20 offices with representation across most of the country. We acknowledge that Deloitte offices stand on traditional, treaty, and unceded territories in what is now known as Canada. We recognize that Indigenous Peoples have been the caretakers of this land since time immemorial, nurturing its resources and preserving its natural beauty. We acknowledge this land is still home to many First Nations, Inuit, and Métis Peoples, who continue to maintain their deep connection to the land and its sacred teachings. We humbly acknowledge that we are all Treaty people, and we commit to fostering a relationship of respect, collaboration, and stewardship with Indigenous communities in our shared goal of reconciliation and environmental sustainability.