Practice Lead - Offensive Security & Red Teaming

Position Overview

Graystone Group is exclusively partnered with an established, publicly traded cybersecurity organization seeking an experienced Practice Lead – Offensive Security & Red Teaming to lead, manage, and expand its Canadian offensive security practice.

This is a high-impact leadership opportunity for a technically accomplished cybersecurity professional who combines deep expertise in penetration testing, red teaming, and adversarial security assessments with the ability to lead technical teams, manage enterprise client engagements, and drive the growth of a revenue-generating professional services practice.

The Practice Lead will oversee the delivery and continued development of the organization's offensive security capabilities, including network and application penetration testing, red team operations, adversary simulation, and emerging AI red teaming services. The individual will also play a key role in developing new service offerings, supporting business development, and expanding the organization's presence across the Canadian market.

The ideal candidate is a proven offensive security practitioner who has progressed into practice leadership while maintaining strong technical credibility, a client-focused approach, and a commercial mindset.

Key Responsibilities

Offensive Security Practice Leadership

• Lead and oversee the Canadian offensive security practice, including penetration testing, red teaming, adversary simulation, and vulnerability assessments.
• Manage, mentor, and develop a team of penetration testers, offensive security consultants, and technical security specialists.
• Provide technical leadership and quality oversight across complex engagements involving enterprise networks, applications, APIs, cloud environments, and infrastructure.
• Establish and continuously improve testing methodologies, technical standards, reporting processes, and engagement delivery frameworks.
• Serve as a senior technical escalation point and trusted advisor for complex client security challenges.
• Maintain hands-on technical involvement when necessary while providing strategic direction to the practice.

AI Red Teaming & Emerging Security Services

• Lead the development and expansion of AI red teaming and adversarial AI security assessment capabilities.
• Oversee security assessments of large language models (LLMs), generative AI applications, autonomous AI agents, and enterprise AI integrations.
• Guide testing methodologies addressing prompt injection, jailbreaks, data leakage, insecure tool use, agent manipulation, and other AI-specific vulnerabilities.
• Apply established and emerging frameworks, including the OWASP Top 10 for LLM Applications and MITRE ATLAS.
• Identify opportunities to develop repeatable AI security testing methodologies, automation capabilities, and new client-facing service offerings.
• Collaborate with technical leadership to position the organization at the forefront of emerging offensive security and AI security services.

Professional Services & Client Delivery

• Oversee the successful execution of offensive security engagements for enterprise and government customers.
• Partner with clients to define engagement objectives, establish technical scope, and recommend appropriate security testing approaches.
• Lead technical discussions, communicate findings, and present actionable security recommendations to senior technical and executive stakeholders.
• Support the development of statements of work (SOWs), proposals, technical presentations, and consulting engagements.
• Ensure engagements are delivered on time, within scope, and in accordance with established quality and profitability expectations.
• Build and maintain strong client relationships while identifying opportunities for expanded security services.

Practice Growth & Business Development

• Partner with executive leadership and sales teams to drive the growth of the Canadian offensive security practice.
• Contribute to practice strategy, revenue growth, service development, and market positioning.
• Support client acquisition, strategic account expansion, and technical pre-sales activities.
• Participate in resource planning, consultant utilization, delivery profitability, and overall practice performance.
• Identify emerging market opportunities and translate customer requirements into commercially viable cybersecurity offerings.
• Recruit, develop, and retain technical talent as the practice continues to expand.

Digital Forensics & Incident Response

• Collaborate with digital forensics and incident response teams to support complex security engagements where applicable.
• Provide technical oversight or advisory support for incident investigations, post-incident assessments, and related security services.
• Identify opportunities to integrate offensive security testing with incident readiness, threat detection, and response capabilities.

Required Qualifications

• 10+ years of progressive cybersecurity experience, including significant expertise in penetration testing, offensive security, or red teaming.
• Demonstrated experience leading an offensive security, penetration testing, or cybersecurity consulting team or practice.
• Strong technical background in network, infrastructure, application, API, and cloud security testing.
• Experience delivering client-facing cybersecurity consulting or professional services engagements.
• Proven ability to manage technical consultants, oversee multiple engagements, and maintain high standards of delivery quality.
• Strong understanding of adversarial testing methodologies, attack techniques, and modern offensive security frameworks.
• Working knowledge of AI security risks, LLM vulnerabilities, and emerging AI red teaming methodologies.
• Experience supporting business development, technical proposals, SOW development, and client engagement scoping.
• Excellent communication and relationship management skills, with the ability to engage technical teams and executive stakeholders.
• Ability to balance technical leadership, operational execution, and commercial practice growth.
• Must be based in Canada.

Preferred Qualifications

• Experience building, scaling, or managing a revenue-generating offensive security consulting practice.
• Hands-on experience with AI red teaming, LLM security assessments, or adversarial testing of generative AI applications.
• Familiarity with OWASP, MITRE ATT&CK, MITRE ATLAS, PTES, and related offensive security frameworks.
• Experience with penetration testing and red teaming tools such as Burp Suite, Metasploit, Cobalt Strike, BloodHound, Nmap, and custom Python-based tooling.
• Exposure to AI security testing tools or frameworks such as PyRIT, garak, or comparable technologies.
• Experience with digital forensics, incident response, threat hunting, or purple teaming.
• Experience managing practice revenue, delivery margins, consultant utilization, or P&L performance.
• Relevant certifications such as OSCP, OSEP, OSCE3, CRTO, GXPN, GPEN, CISSP, or equivalent practical experience.
• Experience supporting enterprise, financial services, critical infrastructure, or government customers.

Ideal Candidate

The ideal candidate is an established offensive security leader with a strong foundation in hands-on penetration testing and red teaming who has successfully transitioned into leading technical teams and managing client-facing professional services engagements.

This individual understands both the technical and commercial aspects of operating a cybersecurity consulting practice and brings the credibility to lead experienced penetration testers while partnering with executive leadership to expand the business.

They will also bring a strong interest in emerging technologies, particularly AI security and adversarial testing, and the ability to help develop and commercialize new capabilities as enterprise adoption of artificial intelligence accelerates.

Above all, this is an opportunity for a technically credible, commercially minded leader to take ownership of a growing offensive security practice and play a meaningful role in its continued expansion across Canada.