Senior Penetration Testing Engineer

Microsoft • Washington, DC

4d • $119,800 - $261,000

About The Position

The Business Security Assurance Pentest Team tests Microsoft products and services used in regulated industries, including commerce, healthcare, finance, HR and legal. As a Senior Penetration Testing Engineer, you will identify vulnerabilities in traditional systems and AI systems, and help scale the team’s testing capabilities. The role covers Microsoft services, cloud infrastructure, identity, APIs and applications, as well as generative AI, AI agents and Model Context Protocol (MCP) integrations.

You will collaborate across groups to communicate security priorities and issues, support remediation, and help advance security practices across the Microsoft Security community. The role also involves using AI agents to accelerate reconnaissance, triage and regression testing with clear guardrails and human sign-off, and translating emerging attack research into guidance, training and awareness.

Requirements

• Master's degree in Statistics, Mathematics, Computer Science or a related field and 3+ years of experience in security or a related field; or bachelor's degree in one of these fields or a related field and 4+ years of experience in security or a related field; or equivalent experience.
• Must be able 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.

Nice To Haves

• 5+ years of hands-on penetration testing or red teaming across cloud (Azure, AWS, GCP), web and API, identity, and network.
• Hands-on experience assessing LLM applications or AI agents in production or pre-production, using the OWASP LLM Top 10, OWASP Agentic AI guidance and MITRE ATLAS.
• Understanding of modern AI architectures, including RAG, agent orchestration frameworks, function and tool calling, MCP, and cloud AI platforms such as Azure AI Foundry, Azure OpenAI, Amazon Bedrock or Vertex AI.
• Strong Python coding skills plus one or more of C#, Go, PowerShell, JavaScript/TypeScript or Rust, and ability to turn research into tools for engagements.
• Experience with tools such as Burp Suite Pro, Metasploit, Cobalt Strike or Sliver, and AI tooling.
• Familiarity with governance and regulatory frameworks relevant to regulated industries, such as NIST AI RMF, EU AI Act, ISO 27K, HIPAA, PCI-DSS and SOC2.
• Experience with APT emulation, purple teaming, threat intelligence, or bypassing operating systems and security control mitigations, including AI guardrails and content filters.
• Certifications such as OSCP, OSEP, GPEN, GWAPT or GXPN, and AI-security credentials.
• Strong teamwork, comfort with ambiguity, and ability to mentor peers and learn new attack techniques quickly.

Responsibilities

• Plan, research and conduct manual penetration tests simulating real-world attackers against Microsoft services, cloud infrastructure, identity, APIs and applications in regulated industries.
• Assess LLM-powered and agent-based applications for prompt injection, jailbreaks, system-prompt and sensitive-data leakage, insecure output handling, misuse of tool and function calls, excessive agent permissions, and abuse of agent memory and context.
• Assess the security of agents and MCP servers, including tool permissions, authentication and authorization between agents and tools, trust boundaries, and the potential impact of a compromised agent.
• Assess AI supply chains and data pipelines, including RAG data sources, vector stores, model and plugin provenance, and risks from poisoned training or fine-tuning data.
• Chain findings across application, cloud, identity and network layers into realistic attack paths that demonstrate business and customer impact.
• Clarify priorities and dependencies across groups, explain key security issues to upper management, and work with partners to implement fixes.
• Use AI agents to speed up reconnaissance, triage and regression testing, with clear guardrails and human sign-off.
• Follow new attack research and turn it into team guidance, training and awareness across the Microsoft Security community.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior