Offensive Security Engineer

Stripe

8d•$170,400 - $255,700•Remote

About The Position

Stripe is seeking an Offensive Security Engineer to join their Proactive Threat team. This role involves identifying vulnerabilities and security weaknesses across Stripe's systems, applications, networks, and cloud infrastructure before adversaries can exploit them. The team operates as a hybrid offensive function, conducting penetration testing, emulating threat actors through red team operations, and collaborating with defensive security teams to enhance Stripe's security posture. A key aspect of this role is developing custom tooling, automation frameworks, and internal platforms to scale offensive capabilities and ensure repeatable, high-fidelity assessments. The ideal candidate is a blend of hacker and engineer, with the team being distributed across the United States and collaborating with global stakeholders.

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

Nice To Haves

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

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