This is a remote position.
Requirements
Scoping & Sizing: Conduct T-shirt sizing (Small, Medium, Large) and scoping for onboarded applications based on dynamic web pages and user roles.
Penetration Testing Execution: Execute manual and tool-assisted grey-box penetration tests across approximately 123 Web/API applications (30 Large, 51 Medium, 42 Small), completing testing within 5–10 days per application.
Engagement Lifecycles: Manage the end-to-end testing lifecycle for each application from kickoff meeting to final sign-off within 20–25 days.
In-Depth Vulnerability Assessment: Conduct expert manual assessments covering authentication, session management, MFA bypass, horizontal/vertical privilege escalation, IDOR/BOLA, API vulnerabilities, and business logic workflow abuses.
Attack-Path Validation: Chain vulnerabilities into realistic attack paths and perform controlled, non-destructive validation within live healthcare environments without disrupting operational or clinical systems.
Platform Management: Deploy and operate a browser-based, RBAC/MFA-enabled pen test platform supporting 6–12 month forward scheduling, metric dashboards, report retention, automated notifications, and GRC tool integration.
Tooling & Environment Setup: Install, configure, and maintain all necessary licensed testing tools inside the client-provided penetration testing machines accessed via the Privileged Access Management (PAM) platform.
Reporting & Debriefs: Author comprehensive reports with testing methodologies, scorecards, reproducible steps, root-cause analyses, and prioritized remediation guidance, followed by stakeholder presentations.
Remediation Tracking & Retesting: Follow up with application owners on vulnerability mitigations and perform targeted retests on resolved findings.
Required Qualifications & Experience
Certifications: Active penetration testing certification such as OSCP (Offensive Security Certified Professional), CEH (Certified Ethical Hacker), or an equivalent credential.
Seniority Threshold (Expert Level):
Relevant Degree + minimum 6 years of consulting experience.
Relevant Diploma + minimum 7 years of consulting experience.
Relevant Certificate + minimum 8 years of consulting experience.
Minimum 10 years of directly related consulting experience.
Healthcare & Production Experience: Demonstrated experience performing penetration testing safely in Canadian healthcare or sensitive enterprise environments with zero clinical/operational impact.
Employment Status: Must be a permanent employee of the service provider (subcontracting is prohibited).
Framework Alignment: Practical working knowledge of OWASP, NIST SP 800-53A, PCI DSS 11.3, and IDART standards
Skills Required
- Active penetration testing certification such as OSCP, CEH, or equivalent
- Relevant degree and at least 6 years of consulting experience
- Relevant diploma and at least 7 years of consulting experience
- Relevant certificate and at least 8 years of consulting experience
- At least 10 years of directly related consulting experience
- Experience performing penetration testing safely in Canadian healthcare or sensitive enterprise environments without clinical or operational impact
- Must be a permanent employee of the service provider; subcontracting is prohibited
- Practical working knowledge of OWASP, NIST SP 800-53A, PCI DSS 11.3, and IDART standards
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What We Do
Workiy is a global company with more than 20 years of experience that provides end-to-end digital solutions, consulting and implementation services to its clients, including digital solutions and staffing services.
