Director, Offensive Security (AI)

Location: Toronto, Canada; remote work available across Canada

Annual base salary: CAD 138,200–181,400, plus potential bonuses and benefits

Company

hirify.global provides SaaS solutions for sales performance management and revenue optimization for organizations worldwide.

What you will do

• Define and execute the offensive security strategy, roadmap, standards, reporting, and risk-reduction metrics.
• Lead internal and external teams across penetration testing, red teaming, AI security testing, vulnerability research, and testing vendor engagements.
• Oversee web, API, mobile, cloud, container, and AI-enabled product security testing, including adversary simulations and purple team exercises.
• Design AI red-team activities for LLM-enabled products and agentic workflows, integrating security throughout the AI development lifecycle.
• Drive vulnerability triage, prioritization, remediation, retesting, attack surface management, bug bounty, and vulnerability disclosure programs.
• Partner with Engineering, Product, Security Operations, Compliance, and Legal teams, and communicate security risks and recommendations to senior leadership.

Requirements

• 10+ years of Information Security experience, including 5+ years in Offensive Security and 3+ years in Development or Engineering.
• Experience leading offensive security programs in SaaS and cloud environments.
• Hands-on expertise in 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 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.

Nice to have

• OSCP, OSWE, GXPN, GPEN, CISSP, CCSP, or cloud security certifications.

Culture & Benefits

• Remote and hybrid options are available across most regions.
• Comprehensive medical, dental, and vision coverage.
• PTO, public holidays, and dedicated volunteer days.
• Dedicated learning days, tuition assistance, and professional development support.
• Retirement plans and compensation aligned with market value.
• Diverse, collaborative, and equal-opportunity work environment.

Hiring process

• Candidate screening and assessment may use artificial intelligence tools alongside human decision-making.
• Salary and compensation are assessed based on qualifications and market data during the interview process.