Senior Network and Cloud Penetration Tester

BMO•VIRTUAL59 - REMOTE/TELETRAVAIL - ON - BMO, ON

8d•CA$103,200 - CA$192,000•Remote

About The Position

Join a team where your work goes beyond checklists protecting critical Network and Cloud environments with real business and regulatory impact. This role offers high-impact, meaningful work where you will directly influence the security of Network/Cloud environments and AI solutions that support applications that matter to customers, regulators, and the business. The focus is on deep, manual penetration testing (Network, Cloud, and AI with human in the loop)—not automated, scanner-driven assessments. You will experience accelerated technical growth by working in complex, enterprise-scale environments that expose you to advanced architectures and evolving threats. You will have end-to-end ownership, engaging across the full lifecycle: scoping → testing → reporting → remediation, with visibility and influence throughout. You will use modern tools and techniques to enhance testing depth and efficiency, experiencing fewer, higher-quality engagements versus consulting-style, high-volume work. Ongoing training is expensed. This is a remote position within Canada, within EST or CST time zones.

Requirements

Minimum of 5+ years experience with Manual Penetration Testing of Networks, and Cloud Environments.
Strong proficiency with Active Directory Environments and associated vulnerabilities and exploitation techniques.
Deep experience with Cloud Environments and associated vulnerabilities in commonly used features utilized in large multi-tenant and hybrid enterprise environments.
Strong proficiency with security testing tools and penetration testing Linux distributions such as Kali.
Deep practical knowledge of applying the Mitre Attack framework.
Strong experience Network and Cloud architecture understanding.
Proficiency in at least one scripting language.
Ability in documenting reproducible steps for technical accurate findings.
Ability to identify and exploit vulnerabilities in Active Directory environments and Cloud workflows as well as multi-step attack paths.
5-8 years of experience in the areas of information systems, software development, and/or information security experience desired.
Strong written and verbal skills with the ability to present complex technical observations to a non-technical audience.
Good time management skills; the ability to commit and adhere to time-sensitive deliverables.
Ability to work remotely, with or without others, take direction, and be a self-starter that takes initiative.
Ability to lead conference calls, be the main point of contact, lead report generation activities, and be the main interface with internal teams on engagements.
Bachelor’s degree in Information Security, Information Technology, Information Systems Management, Computer Science, Engineering or related field(s) or equivalent demonstrated work experience.

Nice To Haves

Experience with security testing of agentic AI solution is a plus.
Experience with security testing of CI/CD pipelines is a plus.
Preference for candidates who have at least one certification in a related field, with strong preference for Information security certifications from a well-recognized institution (e.g. OSCP, OSEP, HackTheBox Cloud security testing certificates, etc).

Responsibilities

Penetration Testing - Responsible for execution of security testing projects according to a structured process, to include writing test reports. This may include oversight and/or execution of the configuration and deployment of security testing software and application of results to security analysis.
Assists with the execution of highly technical/analytical security assessments of Active Directory environments, network infrastructure, cloud environments, and AI technologies, including manual, custom and industry known attack methods using a risk-based intelligence-led methodology.
Identifies potential misuse scenarios.
Advises on secure development practices.
Subject Matter Expertise - Provides technical leadership to business areas as a Security Testing subject matter expert.
Assists with efforts on the execution of security testing operations to include pre-engagement (scoping), engagement (testing) and post-engagement activities (reporting).
Team Leadership - Assists security testing activities aimed at exploiting vulnerabilities in order to enhance the security of BMO network, cloud, and AI technologies.
Works with management and peers to foster the development of less experienced Security Testing Consultants.
Information Security Risk Management - Works with leadership to mature security testing team capabilities including reporting and remediation guidance in alignment with local and global regulatory requirements.
Identifies security gaps and deficiencies by conducting risk assessments; able to recommend corrective action of identified vulnerabilities and weaknesses.
Assists with the execution of planning, testing, tracking, and advises on necessary risk acceptance for identified security risks.
Performs hands-on penetration testing for BMO overall and businesses/groups.
Liaises with stakeholders to understand problems and opportunities and enables BMO to meet its goals by understanding business vision, objectives and KPIs.
Provides technical consultation to business areas as a Security Testing subject matter expert.
Assists with efforts on the execution of security testing operations to include pre-engagement (scoping), engagement (testing) and post-engagement activities (reporting).
Understands and can explain to others the core processes, risks and mitigation techniques for identified security gaps.
Develops and champions information security best practices, including staying abreast of industry information security and business trends through participation in professional associations.
Facilitates discussions and follows a disciplined approach to plan, elicit, analyze, document, communicate and manage initiatives and issues with stakeholders by applying a variety of elicitation techniques to probe, challenge and understand associated risks.