Senior Penetration Testing Engineer

Microsoft • Redmond, WA

3d • $119,800 - $234,700

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. The Senior Penetration Testing Engineer identifies vulnerabilities in traditional systems and AI systems, including generative AI, AI agents, and Model Context Protocol (MCP) integrations, and helps scale testing practices. The role involves collaborating across teams to improve security standards and support Microsoft’s mission and values.

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 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, or 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 retrieval-augmented generation (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 coding skills in Python and 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, 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 the 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.
• Test 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 agent compromise.
• Assess AI supply chains and data pipelines, including retrieval 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 accelerate reconnaissance, triage, and regression testing, with clear guardrails and human sign-off.
• Keep up with 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