Director, Offensive Security

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About the Role

Werelooking for a hands-on Director of Offensive Security to lead and evolve our offensive security program across applications cloud environments enterprise systems and AI-enabled products.

This role combines technicalexpertise strategic leadership and cross-functionalpartnershipto helpidentify prioritize and reduce security risk at offensive security initiatives including penetration testing red teaming AI security validation vulnerability management and bug bounty programs while partnering closely with Engineering Product Security Compliance and Legal teams.

What Youll Do

Lead the Offensive Security Program

• Define and execute the offensive security strategy and roadmap.

• Lead internal and external teams across penetration testing red teaming AI security testing and vulnerability research.

• Establish standards reporting and metrics that drive measurable risk reduction.

Drive Security Testing & Validation

• Oversee web API mobile cloud and AI-enabled security testing.

• Lead red team operations adversary simulations and purple team exercises.

• Manage external penetration testing engagements and testing vendors.

• Mature attack surface management and continuous security validation programs.

Secure AI-Enabled Products

• Design and execute AI red teaming activities for LLM-enabled products and agentic workflows.

• Partner with AI and engineering teams to integrate security throughout the AI development lifecycle.

• Build scalable approaches for AI security testing validation and risk assessment.

Improve Vulnerability Management

• Drive vulnerability triage prioritization remediation and retesting.

• Partner with engineering teams to implement risk-based remediation practices.

• Mature bug bounty and vulnerability disclosure programs.

Influence Across the Business

• Partner with Engineering Product Security Operations Compliance and Legal teams.

• Communicate security risks trends and recommendations to senior leadership.

• Help shape the future of AI-enabled offensive security across the organization.

What Youll Bring

• 10 years of Information Security experience including 5 yearsinOffensive Security and 3 yearsinDevelopment or Engineering.

• Experience leading offensive security programs in SaaS and cloud environments.

• Hands-onexpertisein penetration testing red teaming vulnerability management and security testing of AI-enabled products.

• Strong understanding of application security cloud security attack surface management and secure development practices.

• Experience working with modern cloud environments APIs web applications containers and AI/LLM technologies.

• Ability to translate technical findings into business risk and influence stakeholders at all levels.

• Relevant certifications such as OSCP OSWE GXPN GPEN CISSP CCSP or cloud security certifications are considered an asset.

What Success Looks Like

First 90 Days

• Assess the current offensive security landscape andidentifykey opportunities for improvement.

• Build relationships across engineering security and business teams.

• Establish priorities and define a roadmap for continuous security validation.

6 Months

• Scale AI-enabled offensive security capabilities.

• Improve vulnerability management effectiveness and remediation outcomes.

• Deliver measurable reductions in organizational security risk.

Long-term (7 months): Mature Measure & Reduce Risk

• Scale autonomous vulnerability management across critical assets and environments.

• Mature AI-enabled red team capabilities and continuous threat-informed security validation.

• Drive measurable reductions in organizational risk through AI-enabled offensive security capabilities.

For this role the estimated annual base salary range is between $138200.00 $159800.00 (CAD). In addition to base salary our compensation package may include bonuses commissions for eligible sales roles and a comprehensive benefits package. The actual base salary will vary based on factors including individual qualifications and market data as objectively assessed during the interview process.

This posting is for anewvacancy.

This hiring process utilizes artificial intelligence tools to assist in candidate screening and assessment. Our AI tools are designed to complement not replace human decision-making.

Overview of Benefits:

• Health & Wellness Comprehensive medical dental and vision coverage tailored to your local needs
• Time Off PTO and public holidays to rest recharge and do what matters most
• Volunteer Days Dedicated time to give back and support the communities that matter to you
• Ignite Days Dedicated learning days to support continuous growth skill development and professional learning
• Financial Compensation that reflects your market and your value
• Retirement Retirement plans designed to help you build long-term financial security
• Tuition Assistance Invest in your growth with support for continuing education and professional development
• Flexibility Work where you thrive with remote and hybrid options available across most regions