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 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
Who you are
We're looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirements, you are encouraged to apply. The preferred qualifications are a bonus, not a requirement.
Minimum 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
Preferred qualifications
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
Location
This role is remote within the United States. While you are welcome to visit Stripe offices for team meetings, on-sites, and events, our expectation is that you would regularly work from home. The team primarily coordinates across Eastern and Pacific time zones, with regular collaboration with stakeholders in Europe and Asia.
Compensation & Benefits
The annual US base salary range for this role is $170,400 – $255,700. This range may span multiple career levels and will be refined during the interview process based on experience, qualifications, and location.
Additional benefits include
Equity participation in Stripe's growth
401(k) plan with matching contributions from day one
Comprehensive medical, dental, and vision coverage
Wellness stipends
Annual budget for training, certifications, and conference attendance
