CareerPlan

Director, Offensive Security

Canada - RemoteRemoteFull-timeCA$138k–CA$181k2026-10-24 → 2026-11-10
Hybrid

Core

Lead and evolve the offensive security program across applications, cloud environments, enterprise systems, and AI-enabled products to identify, prioritize, and reduce security risk at scale.

Role type

Director, Offensive Security (Hands-on IC with strategic leadership)

Builds

Offensive security strategy, red team operations, AI security validation programs, and vulnerability management frameworks

Domain

Cybersecurity (Offensive Security, Cloud Security, AI Security)

Required skills

Offensive security strategy, penetration testing, red teaming, AI security testing, vulnerability management, attack surface management, cloud security, application security, stakeholder influence, roadmap definition

Preferred skills

OSCP, OSWE, GXPN, GPEN, CISSP, CCSP, cloud security certifications

Technologies

Web applications, APIs, mobile, cloud environments, containers, AI/LLM technologies, agentic workflows

Responsibilities

Define and execute offensive security strategy and roadmap; Lead internal and external teams across penetration testing, red teaming, and AI security testing; Oversee web, API, mobile, cloud, and AI-enabled security testing; Drive vulnerability triage, prioritization, and remediation; Partner with engineering and product teams to integrate security into the AI development lifecycle; Communicate security risks and recommendations to senior leadership

Seniority

Director, strategic leadership with hands-on technical execution