Principal Penetration Tester

Microsoft•Redmond, WA

6d•$142,800 - $304,200•Hybrid

About The Position

Join Microsoft’s Cloud Operations + Innovation (CO+I), the organization behind the technology and infrastructure that powers Microsoft’s cloud. The Trusted Cyber Engineering (TCE) team helps secure global operations by testing the physical and logical security systems that support Microsoft’s global datacenters, including cloud services, networks, hardware, and operational technology for critical infrastructure such as power, cooling, and building management systems. This is a hands-on individual-contributor role and technical lead for the penetration testing function. The successful candidate will help shape team priorities, tactics, methodologies, strategy, and growth while collaborating closely with partners to perform penetration testing and drive issue resolution. The role also involves educating and mentoring cyber defenders, peers, and strategic partners. There is a preference for working from Microsoft’s Redmond, Washington office three days per week, but qualified candidates unable to meet this preference are welcome. The role requires a relevant master’s degree and four or more years of security or related experience, a relevant bachelor’s degree and six or more years of such experience, or equivalent experience. The successful candidate must pass Microsoft’s Cloud Background Check upon hire or transfer and every two years thereafter. Citizenship verification is also required because the position supports U.S. government agency customers and is subject to citizenship-based legal restrictions; citizenship will be verified with a valid passport.

Requirements

Master’s degree in Statistics, Mathematics, Computer Science, or a related field and at least 4 years of experience in security or a related field; or a bachelor’s degree in one of these fields and at least 6 years of relevant experience; or equivalent experience.
Ability to meet Microsoft, customer, and/or government security screening requirements, including passing the Microsoft Cloud Background Check upon hire or transfer and every two years thereafter.
Citizenship verification with a valid passport, required due to citizenship-based legal restrictions associated with supporting U.S. federal, state, and/or local government agency customers.

Nice To Haves

At least 6 years of experience identifying security vulnerabilities and working with software development lifecycles, large-scale computing, modeling, cybersecurity, and anomaly detection.
At least 6 years of coding or scripting experience with languages such as C#, Python, C++, Go, PowerShell, .NET, or Rust, or comparable languages.
Familiarity with security standards and frameworks such as OWASP, MITRE ATT&CK, and NIST.
At least 3 years of experience leading a penetration-testing team, including hiring, mentoring, and managing full-time and vendor engineers.
Relevant offensive security certifications such as OffSec OSCP, OSEP/OSCE³, GPEN, or GXPN; OT/ICS certifications such as GICSP or GRID.
Experience using open-source and open-weight large language models (LLMs), as well as chunking, embeddings, and retrieval-augmented generation (RAG) techniques.
Expertise developing KQL queries and data models, anomaly detection, correlation analytics, and statistical analysis.
Deep understanding of Azure and experience with AWS or GCP.
Knowledge of operational technology (OT) and Industrial Control Systems (ICS) security.
Effective organizational and technical program management skills and demonstrated ability to convey complex concepts to diverse audiences.
Proficiency with Power BI and Azure DevOps for reporting and tracking.

Responsibilities

Lead and participate in comprehensive penetration tests across applications, cloud, networks, hardware, and critical-infrastructure operational technology systems.
Identify vulnerabilities and perform end-to-end adversary emulation within approved rules of engagement across multiple areas of responsibility.
Operate in uncertain, challenging, and novel environments; conduct offensive and defensive security operations and identify previously unknown areas of risk.
Build relationships and advocate for security changes to enable efficient organizational communication and collaboration.
Provide strategic guidance on team priorities, tactics, evaluation strategies, and methodologies; chain findings into attack paths that demonstrate operational and business impact.
Organize and direct team work on engagement rules, scoping, executive risk communications, and technical guidance for operations.
Lead the team’s operating rhythm and ensure findings are remediated according to defined SLAs and that reporting and communications are delivered on time.
Create executive-level written and verbal presentations that explain penetration testing and technical information to non-technical audiences; present data-driven reporting on operations, impact, risks, vulnerabilities, system information, and remediation plans.
Work as a technical operator across penetration-testing offerings, identify and exploit misconfigurations, improve detection capabilities, and enhance threat visibility.
Research emerging threats, vulnerabilities, tools, attack techniques, and security trends.
Mentor and guide team members and partners, fostering curiosity, collaboration, and technical excellence.
Partner with detection, threat intelligence, and incident response teams to turn findings into actionable detections.
Apply AI and automation to scale reconnaissance, discovery, and testing.