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Role Overview: We are seeking an experienced and technically proficient Senior Cybersecurity Specialist to support and enhance our organization’s offensive security capabilities. In this role, you will conduct and coordinate penetration tests, red team activities, and targeted security assessments across enterprise systems, web applications, and cloud environments. You will work closely with infrastructure, engineering, and DevSecOps teams to identify vulnerabilities, reduce the attack surface, and strengthen overall security resilience.

Sobeys is full of exciting opportunities, and we are always looking for bright new talent to join our team! We currently have a full-time opportunity for a Senior Cyber Security Specialist. This role can be based out of one our main offices including: Mississauga, ON. Calgary, AB; Burnaby, BC; Stellarton, NS.

Key Responsibilities: 

• Plan, coordinate, and execute in-depth penetration test across internal systems, External systems, web applications, APIs, and cloud environments.
• Perform comprehensive Static and Dynamic Application Security Testing (SAST/DAST) across enterprise, SaaS, and internally developed applications.
• Conduct secure code review and identify vulnerabilities, design weaknesses, and potential exploitation paths.
• Assess, validate, and prioritize vulnerabilities, providing practical remediation recommendations aligned with business and compliance requirements.
• Collaborate with infrastructure, platform, and DevOps teams to integrate effective security controls into CI/CD and MLOps workflows.
• Evaluate web and mobile applications for security flaws such as insecure APIs, injection vulnerabilities, and misconfigurations.
• Contribute to red team initiatives and advanced adversarial assessments, ensuring realistic threat modeling and high-quality deliverables.
• Manage the end-to-end scoping, execution, and reporting of security engagements while maintaining accuracy, reproducibility, and actionable risk context.
• Develop and maintain security documentation, standards, and reporting templates to ensure consistency and compliance.

#LI-Hybrid     #LI-VJ1

Required Skills & Experience :

• Minimum 5+ years of hands-on experience in offensive security, penetration testing, or red teaming.
• Strong understanding of application security principles and manual testing methodologies (OWASP, ASVS, WSTG, NIST 800).
• Proficiency with penetration testing tools, including Nmap, Nessus, Metasploit, Burp Suite etc..
• Experience performing SAST, DAST, and code-level exploit development in languages such as C, C++, Java, or C#.
• Administrator-level familiarity with Unix and Windows environments.
• Proven ability to analyze false positives, validate findings, and articulate technical risk effectively.
• Strong grasp of OWASP frameworks across Web, API, Mobile, and AI/LLM surfaces.

Preferred Qualifications :

• Offensive security certifications (e.g., OSCP, OSEP, OSCE, GPEN, GWAPT)
• Experience with cloud security and scripting for automation in offensive security contexts.
• Familiarity with secure SDLC practices and working alongside software engineering teams.

Who We Are Looking For : 

• A curious and detail-oriented thinker who digs deep into issues until the full impact is understood.
• A strong communicator who can translate technical findings into business-relevant insights.
• Self-driven and continuously learning, with a passion for staying ahead in the ever-evolving cybersecurity landscape.
• Dependable and team-oriented, capable of collaborating across technical and leadership level.