Director, Offensive Security (Cybersecurity)

TL;DR

Director, Offensive Security (Cybersecurity): Leading and evolving the offensive security program across applications, cloud, and AI-enabled products with an accent on red teaming and vulnerability management. Focus on designing AI security validation, scaling attack surface management, and reducing organizational risk through strategic adversary simulations.

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

Salary: $138,200 - $181,400 CAD

Company

hirify.global is a market-leading SaaS company providing Sales Performance Management (SPM) solutions to global industry leaders.

What you will do

• Define and execute the offensive security strategy and roadmap to reduce risk at scale.
• Lead penetration testing, red teaming, adversary simulations, and purple team exercises.
• Design and execute AI red teaming for LLM-enabled products and agentic workflows.
• Oversee web, API, mobile, and cloud security testing, including vendor management.
• Drive vulnerability triage, prioritization, and risk-based remediation practices.
• Communicate security risks, trends, and strategic recommendations to senior leadership.

Requirements

• 10+ years of Information Security experience, with 5+ years in Offensive Security and 3+ years in Development or Engineering.
• Hands-on expertise in penetration testing, red teaming, and AI-enabled product security.
• Deep understanding of application security, cloud environments, containers, and LLM technologies.
• Proven ability to translate complex technical findings into business risk for stakeholders.
• Must be based in Toronto, Canada, or eligible for the available remote/hybrid options in the region.

Nice to have

• Certifications such as OSCP, OSWE, GXPN, GPEN, CISSP, CCSP, or cloud security credentials.

Culture & Benefits

• Comprehensive medical, dental, and vision coverage.
• Generous PTO, public holidays, and dedicated volunteer days.
• Ignite Days for continuous learning and professional skill development.
• Retirement plans and tuition assistance for continuing education.
• Flexible work environment with remote and hybrid options.