Director, Offensive Security (AI)

TL;DR

Director, Offensive Security (AI): Leading and evolving the offensive security program across SaaS, cloud, and AI-enabled products with an accent on penetration testing, red teaming, and vulnerability management. Focus on building scalable AI security validation, driving risk-based remediation, and influencing cross-functional stakeholders to reduce organizational security risk.

Location: Toronto, Canada (Remote and hybrid options available)

Salary: $138,200 – $159,800 CAD

Company

hirify.global is a market-leading SaaS provider transforming Sales Performance Management (SPM) and revenue optimization for global organizations.

What you will do

• Define and execute the offensive security strategy, roadmap, and risk-reduction metrics.
• Lead internal and external teams in penetration testing, red teaming, and AI security validation.
• Design and implement scalable approaches for testing LLM-enabled products and agentic workflows.
• Drive vulnerability triage, prioritization, and remediation in partnership with engineering teams.
• Communicate security risks, trends, and strategic recommendations to senior leadership.
• Mature attack surface management and continuous security validation programs.

Requirements

• 10+ years of Information Security experience, including 5+ years in Offensive Security.
• 3+ years of experience in Development or Engineering.
• Proven experience leading offensive security programs within SaaS and cloud environments.
• Hands-on expertise in penetration testing, red teaming, and vulnerability management.
• Strong understanding of AI/LLM security, cloud security, and secure development practices.
• Ability to translate complex technical findings into business risk for stakeholders.

Nice to have

• Relevant certifications such as OSCP, OSWE, GXPN, GPEN, CISSP, or CCSP.

Culture & Benefits

• Comprehensive medical, dental, and vision coverage.
• Flexible work environment with remote and hybrid options.
• Dedicated learning days (Ignite Days) for professional development.
• Tuition assistance for continuing education.
• Paid time off and public holidays.
• Supportive, diverse, and collaborative team culture.