Security Engineer - Offensive Security

Who we are About Stripe Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world's largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career. About the team The Proactive Threat team is responsible for identifying vulnerabilities and security weaknesses across Stripe's systems, applications, networks, and cloud infrastructure — before adversaries do. We operate as a hybrid offensive function: conducting penetration testing, emulating real-world threat actors through red team operations, and partnering closely with our defensive security teams to validate detection capabilities and improve Stripe's overall security posture. We are builders first. Our team develops custom tooling, automation frameworks, and internal platforms that scale our offensive capabilities and enable repeatable, high-fidelity assessments. We believe the best offensive security engineers are equal parts hacker and engineer. The team is distributed across the United States, primarily operating in Eastern and Pacific time zones, and collaborates regularly with security, engineering, and product stakeholders across Stripe — including teams in Europe and Asia. What you'll do As an Offensive Security Engineer on the Proactive Threat team, you will simulate the tactics, techniques, and procedures (TTPs) of real-world adversaries to uncover security risks across Stripe's products and infrastructure. You'll conduct hands-on penetration testing, lead red team engagements, and collaborate with blue team counterparts to validate and improve detection and response capabilities. Your work will directly influence how Stripe builds, ships, and secures financial infrastructure used by millions of businesses worldwide. Beyond assessments, you'll design and build offensive tooling and automation that amplifies the team's impact. You'll leverage threat intelligence to prioritize testing efforts, contribute to incident investigations when needed, and act as a subject-matter expert for security initiatives across the company. Responsibilities Conduct comprehensive penetration tests across web applications, APIs, cloud environments (AWS/GCP/Azure), mobile applications, and internal infrastructure Plan and execute red team engagements that emulate the TTPs of cyber and criminal threat actors targeting financial services, including initial access, lateral movement, persistence, and data exfiltration scenarios Perform assumed-breach and objective-based assessments to test detection and response capabilities in coordination with defensive teams Partner with detection engineering, threat intelligence, and incident response teams to validate security controls, identify coverage gaps, and improve detection fidelity Contribute adversary tradecraft insights to inform detection rule development, threat hunting hypotheses, and incident response playbooks Support incident investigations by providing offensive expertise, log analysis, and root cause analysis when required Design, develop, and maintain custom offensive tools, scripts, and automation frameworks to enhance assessment efficiency and coverage Build internal platforms and workflows that enable scalable, repeatable offensive operations Contribute to internal security tooling repositories and champion engineering best practices within the team Automate repetitive testing tasks, payload generation, and reporting workflows using modern development practices Produce clear, actionable reports that communicate technical findings, business risk, and remediation guidance to both technical and non-technical stakeholders Act as a subject-matter expert and primary point