Offensive Security Engineer

Stripe is a financial infrastructure platform for businesses. The company is seeking an Offensive Security Engineer to identify vulnerabilities across its systems, applications, networks, and cloud infrastructure through penetration testing and red team operations. The role also involves building offensive security tooling, validating detection capabilities, supporting investigations, and leading security initiatives.

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 of contact for stakeholder teams engaged in offensive security programs and Stripe-wide security initiatives
• Lead offensive security projects end-to-end, mentor junior team members, and foster a culture of continuous learning and knowledge sharing
• Stay current with emerging threats, vulnerabilities, and attack techniques; share research internally and contribute to the broader security community

Requirements:

• 5+ years of experience in offensive security, penetration testing, red teaming, or a related field
• Strong programming skills in Python, Go, or similar languages, with demonstrated experience building tools, automation, or custom exploits
• Deep knowledge of web application security, including OWASP Top 10, ASVS, and common vulnerability classes (injection, auth flaws, business logic, etc.)
• Hands-on experience with cloud platforms (AWS, Azure, or GCP), including cloud-native attack techniques and misconfigurations
• Proficiency with offensive tooling such as Burp Suite, Cobalt Strike, Mythic, Sliver, BloodHound, or similar frameworks
• Familiarity with adversary tradecraft and frameworks such as MITRE ATT&CK, including TTPs for initial access, privilege escalation, lateral movement, and exfiltration
• Excellent written and verbal communication skills, with the ability to translate complex technical findings into clear, risk-based recommendations
• Ability to think like an adversary — creative, persistent, and able to holistically assess risk in complex environments
• This role is remote within the United States
• Experience conducting offensive security in fintech, financial services, or other highly regulated environments
• Background in vulnerability research, exploit development, or CVE discovery
• Experience collaborating with threat intelligence, detection engineering, or incident response teams (purple team operations)
• Familiarity with big data and log analysis tools (Splunk, Databricks, PySpark, osquery, etc.) for threat hunting or investigative support
• Proficiency with AI/LLM-assisted development tools (e.g., Claude Code, Cursor, GitHub Copilot) and experience applying them to offensive security workflows
• Interest or experience in agentic automation — using LLMs or autonomous agents to augment reconnaissance, vulnerability discovery, or exploitation workflows
• Experience testing AI/ML systems or LLM-based applications for security weaknesses (prompt injection, training data extraction, model manipulation, etc.)
• Contributions to open-source security tools, published research, blog posts, or conference presentations
• Relevant certifications such as OSCP, OSWE, OSEP, OSED, CRTO, CPTS, PNPT, GXPN, or cloud security certifications