Senior Network and Cloud Penetration Tester

Bank of Montreal•Virtual, TX

6d•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. High-impact, meaningful work Directly influence the security of Network\Cloud environments and AI solutions that support applications that matter to customers, regulators, and the business. Depth over volume Focus on deep, manual penetration testing (Network, Cloud, and AI with human in the loop)—not automated, scanner-driven assessments. Accelerated technical growth Work in complex, enterprise-scale environments that expose you to advanced architectures and evolving threats. End-to-end ownership Engage across the full lifecycle: scoping → testing → reporting → remediation, with visibility and influence throughout. Modern tools and techniques Use advanced testing tools to enhance testing depth and efficiency. More meaningful engagements Experience fewer, higher-quality engagements versus consulting-style, high-volume work. Ongoing training expensed Work remotely in USA 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

Responsible for execution of security testing projects according to a structured process, to include writing test reports.
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.
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).
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.
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.