Penetration Tester - Infrastructure & Red Team

Location: Fully remote within Canada

Company

hirify.global provides tailored infrastructure penetration testing, cloud security assessments, red team operations, and offensive security consulting services.

What you will do

• Plan and execute infrastructure penetration testing across on-premises, hybrid, cloud, wireless, and enterprise network environments.
• Assess Windows, Linux, Active Directory, Microsoft Entra ID, virtualization platforms, cloud services, containers, Kubernetes, CI/CD pipelines, and cloud-native technologies.
• Conduct red team, adversary simulation, threat emulation, and purple team engagements across the attack lifecycle.
• Identify, validate, and exploit vulnerabilities, privilege escalation opportunities, identity risks, configuration weaknesses, and realistic attack paths.
• Prepare technical reports and present vulnerabilities, business impact, risk ratings, attack paths, and remediation recommendations to technical and executive stakeholders.
• Contribute to methodology development, tooling, automation, technical research, internal training, and knowledge sharing.

Requirements

• Bachelor's degree in Cybersecurity, Computer Science, Information Technology, or a related discipline; equivalent practical experience is considered.
• At least 3 years of professional experience in infrastructure penetration testing, red teaming, adversary simulation, or offensive security consulting.
• Experience conducting penetration testing across enterprise infrastructure, including Windows, Linux, Active Directory, Microsoft Entra ID, cloud platforms, and enterprise networking.
• Experience with internal and external network penetration testing, privilege escalation, Active Directory security assessments, and lateral movement testing.
• Experience assessing AWS, Microsoft Azure, or Google Cloud Platform environments.
• Strong understanding of enterprise networking, authentication technologies, identity management, cloud security, and offensive security methodologies.
• Experience using industry-standard offensive security frameworks, tools, and tradecraft.
• Excellent technical writing, presentation, and communication skills, including communication with technical and executive stakeholders.
• Customer-first mindset, dependable delivery, self-motivation, adaptability, continuous learning, and willingness to investigate findings until their impact is proven.

Nice to have

• OSCP, OSEP, CRTO, CRTE, CARTP, CARTA, CREST CRT, CREST CCT, PNPT, GPEN, GXPN, or equivalent certifications; OSCP or equivalent demonstrated technical capability is strongly preferred.
• Experience participating in or leading Red Team, Purple Team, adversary simulation, or threat emulation engagements.

Culture & Benefits

• Fully remote work within Canada with a flexible work environment.
• Immediate and ongoing offensive security training, mentorship, and professional development.
• Opportunity to contribute to the growth, direction, and methodology of the offensive security practice.
• Collaboration with experienced security professionals focused on technical excellence and disciplined execution.
• Competitive compensation and growth opportunities.
• GRRSP with corporate matching and participation in corporate benefit plans within Canada.