Principal Penetration Tester

Overview

Join Cloud Operations + Innovation (CO+I), the organization behind the technology and infrastructure that powers Microsoft’s cloud. Within CO+I, the Trusted Cyber Engineering (TCE) team is at the forefront of ensuring the security of our global operations.

We are seeking a highly skilled security engineer to join our team dedicated to driving cutting-edge security innovation. You will test physical and logical security systems that keep Microsoft’s global datacenter running, from cloud services and networks to hardware and operational technology for critical infrastructure such as power, cooling, and building management systems. As part of our team, you’ll provide guidance on team priorities, tactics, and methodologies.

You will educate, empower, and inspire fellow cyber defenders, peers, and strategic partners. Our focus is collaboration as we perform penetration testing and ensure a high rate of issue resolution working very closely with our partners. You will be a direct hands-on individual contributor and a technical lead for our penetration testing function with the ability to help shape the team and team’s strategy as we continue to mature our penetration testing team’s capability and growth.

While there is a preference for candidates who can work from our Redmond, WA office three days per week, we welcome qualified candidates who may not be able to meet this preference.

Microsoft’s mission is to empower every person and every organization on the planet to achieve more. As employees we come together with a growth mindset, innovate to empower others, and collaborate to realize our shared goals. Each day we build on our values of respect, integrity, and accountability to create a culture of inclusion where everyone can thrive at work and beyond.

Responsibilities

Leads and participates in comprehensive penetration testing efforts across all layers of services including applications, cloud, network, hardware and critical infrastructure operational technology (OT) systems. Identifies security vulnerabilities, performs end-to-end adversary emulation within approved rules of engagement for multiple areas of responsibility with an ability to come up to speed on new targets and unidentified patterns without direction.

Operates in uncertain, challenging, and novel environments and execute offensive and defensive security operations. Identifies unknown risk areas and leverages expertise to appropriately handle them.

Builds relationships to enable streamlined and efficient communication and collaboration, advocating for security change across the organization.

Provides strategic guidance to teams on priorities, tactics, evaluation strategies, and development of methodologies. Chains findings into attack paths that demonstrate operational and business impact.

Organizes and directs the team focused on engagement rules, scoping, executive risk communications and technical guidance for operations. Leads the rhythm of business across team to ensure remediation of findings is completed according to the defined SLA; reporting and all communications are delivered on time.

Creates high-quality executive level verbal and written presentations advocating for and outlining process of penetration testing, explaining technical information to non-technical audiences, as well as present data driven reporting tracking operations, explaining impact, risks, vulnerabilities, system information and remediation plans with potential impact.

Works as a technical operator on various types of penetration testing offerings with an ability to identify and exploit misconfigurations, improve detection capabilities, and enhance threat visibility.

Research emerging threats, vulnerabilities, and tools to stay updated with the latest attack techniques, and security trends

Mentors and guide team members and partners, fostering a culture of curiosity, collaboration, and technical excellence. Partners closely with detection, threat intelligence and incident response teams to turn findings into actionable detections.

Applies AI and automation to scale reconnaissance, discovery and testing.

Required Qualifications

• Master's Degree in Statistics, Mathematics, Computer Science, or related field AND 4+ years’ experience in security or related field
• OR Bachelor's Degree in Statistics, Mathematics, Computer Science, or related field AND 6+ years’ experience in security or related field
• OR equivalent experience.

Other Requirements

Ability to meet Microsoft, customer and/or government security screening requirements are required for this role. These requirements include, but are not limited to the following specialized security screenings:

Microsoft Cloud Background Check: This position will be required to pass the Microsoft Cloud background check upon hire/transfer and every two years thereafter.

Citizenship & Citizenship Verification: This position requires verification of citizenship due to citizenship-based legal restrictions. Specifically, this position supports United States federal, state, and/or local government agency customers and is subject to certain citizenship-based restrictions where required or permitted by applicable law. To meet this legal requirement, and as a condition of employment, the successful candidate’s citizenship will be verified with a valid passport.

While not required, we also look for the followingPreferred Qualifications:

6+ years of experience in identifying security vulnerabilities, software development lifecycle, large-scale computing, modeling, cyber security, and anomaly detection

6+ years of experience with coding or scripting in languages such as C#, Python, C++, Go, PowerShell, .NET, Rust, or other comparable programming languages

Familiarity with security standards and frameworks like OWASP, MITRE ATT&CK, and NIST.

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, GXPN, or similar; OT/ICS certifications (e.g., GICSP, GRID)

Experience utilizing open-source and open-weight Large Language Models (LLMs), and chunking, embeddings and RAG techniques.

Expertise developing KQL queries, data models, anomaly detection, correlation analytics, statistical analysis.

Deep understanding of Azure; AWS, or GCP experience.

Knowledge of operational technology (OT) and Industrial Control Systems (ICS) security.

Effective organizational and technical program management skills as well as demonstrated skills for conveying complex concepts to diverse audiences.

Proficiency with Power BI and Azure DevOps for reporting and tracking

#COICareers

Penetration Testing IC5 - The typical base pay range for this role across the U.S. is USD $142,800 - $274,800 per year. There is a different range applicable to specific work locations, within the San Francisco Bay area and New York City metropolitan area, and the base pay range for this role in those locations is USD $188,000 - $304,200 per year.

Certain roles may be eligible for benefits and other compensation. Find additional benefits and pay information here:

https://careers.microsoft.com/us/en/us-corporate-pay

This position will be open for a minimum of 5 days, with applications accepted on an ongoing basis until the position is filled.

Microsoft is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, citizenship, color, family or medical care leave, gender identity or expression, genetic information, immigration status, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran or military status, race, ethnicity, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable local laws, regulations and ordinances.

If you need assistance with religious accommodations and/or a reasonable accommodation due to a disability during the application process, read more about requesting accommodations.

Insights from previous hires

Top skills: Automation, Business, Active Directory, Documentation, Computer Science, Communication, Collaborative Environment, Cloud Computing, Assessment, Analytics

Common previous titles: Director Security Engineering, Principal Penetration Testing, Principal Penetration Tester, Penetration Testing Leader, Tech Support Engineer, Vice President Engineering, Senior Security Engineer, Senior Specialist, Senior Intelligence Analyst, Digital Specialist