Toronto Red Team Operator & InfoSec Specialist

TD; Toronto; On-site; CAD 97,000 - 137,000; Full time

Job summary

TD is seeking an Information Security Specialist - Red Team Operator to join its offensive security program in Toronto. The role focuses on end-to-end red team engagements, emulating threat actors to validate controls and provide actionable insights to detection and response teams.

The ideal candidate brings hands-on security expertise, strong tradecraft, and the ability to operate safely in a highly governed enterprise environment.

Qualifications

• University degree
• 7+ years of experience in offensive security, red teaming, penetration testing, or equivalent hands-on security roles
• Strong knowledge of Windows Active Directory environments, identity abuse, and enterprise authentication flows
• Proven experience with common red team tooling (e.g., C2 frameworks, phishing platforms, custom payloads)
• Solid understanding of network protocols, operating systems, and endpoint security controls
• Ability to safely execute adversarial activities in regulated environments with strict scope and approval processes
• Strong written and verbal communication skills, including report writing and technical walkthroughs
• Demonstrated ability to work independently while collaborating effectively with cross-functional teams

Responsibilities

• Plan and execute full-scope red team engagements, including reconnaissance, initial access, lateral movement, privilege escalation, command-and-control, and objective completion
• Emulate real-world threat actors using established TTPs (e.g., MITRE ATT&CK)
• Conduct phishing and social engineering campaigns within defined legal and ethical constraints
• Develop and maintain custom tooling, payloads, and infrastructure to support operations
• Collaborate closely with Blue Team, Purple Team, Threat Intelligence, and Incident Response partners
• Produce clear, technically accurate engagement reports and executive-ready summaries
• Contribute to detection engineering by identifying gaps in controls, telemetry, and response processes
• Support continuous improvement of red team methodologies, playbooks, and governance processes
• Mentor junior operators and contribute to team knowledge sharing

Skills

Offensive security

Red teaming

Penetration testing

Threat emulation

Education

University degree

Tools

C2 frameworks

Phishing platforms

Custom payloads

PowerShell

Python

C#

Job description

TD is seeking an Information Security Specialist - Red Team Operator to join its offensive security program in Toronto. The role focuses on end-to-end red team engagements, emulating threat actors to validate controls and provide actionable insights to detection and response teams.

The ideal candidate brings hands-on security expertise, strong tradecraft, and the ability to operate safely in a highly governed enterprise environment.