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 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

See yourself at Twilio

Join the team as Staff Engineer, Offensive Security

About the job

The Staff Engineer acts as a Technical Lead. You don't just find bugs; you design complex attack chains that demonstrate systemic risk. You spend as much time writing custom code and researching new bypasses as you do executing tests.

Responsibilities

In this role, you will:

• Full-Stack Penetration Testing: Perform manual and automated testing of web applications, APIs, and mobile apps (iOS/Android).
• Internal/External Network Audits: Conduct network and cloud level assessments with various tooling
• Vulnerability Validation: Triage and validate reports from automated scanners or bug bounty hunters to eliminate false positives and escalate true positives
• AI/LLM Probing: Perform initial prompt injection and jailbreak tests on AI prototypes, services, and applications using established checklists (OWASP Top 10 for LLMs).
• Technical Reporting: Draft high-quality reports that detail the "path to compromise" with clear, reproducible steps for developers.
• Tool Maintenance: Manage and update the team's testing infrastructure (e.g., Burp Suite, and basic C2 listeners).
• Remediation Support: Provide direct technical guidance to engineering teams on how to patch vulnerabilities like XSS, SQLi, and IDOR.
• Adversary Emulation: Design and lead multi-week Red Team operations that mimic specific threat actors (APTs) to test the SIRT detection capabilities.
• Custom Exploit Development: Build custom payloads, droppers, and obfuscated scripts to bypass EDR/AV and maintain stealth.
• AI Red Teaming Architecture: Build automated testing frameworks for AI systems (e.g., using PyRIT, Promptfoo, or Garak) to test for models related to sensitive data leakage.
• Cloud & Infrastructure Attacks: Execute sophisticated attacks against AWS/Azure/K8s, focusing on IAM misconfigurations and container escapes.
• Purple Teaming: Collaborate with SIRT and Detection Engineering to tune SIEM alerts based on the techniques used during an engagement.
• Strategic Bug Bounty Management: Oversee the organization's bug bounty program, identifying trends in submissions to suggest broad architectural security changes.

Qualifications

Twilio values diverse experiences from all kinds of industries, and we encourage everyone who meets the required qualifications to apply. If your career is just starting or hasn't followed a traditional path, don't let that stop you from considering Twilio. We are always looking for people who will bring something new to the table!

Required:

• Experience: 7-10 years in offensive security, penetration testing, a high-volume bug bounty background, AppSec, or vulnerability exploitation, and track record of finding high/critical vulnerabilities in complex environments using pentesting commercial or custom tools.
• Concepts: Expert Knowledge and  solid understanding of the MITRE ATT&CK matrix and the OWASP Top 10 for web applications and top 10 for LLMs, post exploitation (lateral movement, persistence, data exfiltration) and Adversarial ML.
• Tooling: Proficient in OffSec popular tools like Burp Suite professional, Nmap, Metasploit, Wireshark etc... and AI security tools such as LangChain, TensorFlow for adversarial testing or, as well as use of C2 frameworks (Cobalt Strike, Sliver, Havoc) or similar tools
• Scripting and Coding: Ability to write functional scripts in Python or Bash to automate repetitive testing tasks and proficiency in coding and scripting like Python, C++, and scripting for creating custom offensive exploits that avoids signature-based detection.
• Certifications: Possession of advanced industry certifications such as OSCP, OSEP, OSWE, GXPN or similar training in OffSec tracks is highly desirable

Desired:

• Telecom expertise is preferred
• Excellent written and verbal communication skills.
• Ability to influence and build effective working relationships with all levels of the organization.
• Proficiency in multiple languages applicable to the region.

Location

This role will be Remote, and based in Ireland

Travel 

We prioritize connection and opportunities to build relationships with our customers and each other. For this role, approximately 15% travel is anticipated to help you connect in-person in a meaningful way.

What We Offer

Working at Twilio offers many benefits, including competitive pay, generous time off, ample parental and wellness leave, healthcare, a retirement savings program, and much more. Offerings vary by location.

Account Executive

Software builders face immense pressure to deliver exceptional user experiences while navigating compressed release cycles and fierce competition in today's software-centric world. The consequences of even a minor mistake can be severe, affecting a company's reputation and future prospects. At SmartBear, we're committed to providing the tools and discipline needed to maintain quality throughout the software development lifecycle. As our company grows and succeeds in the market, we're actively seeking individuals to join us in addressing these unique challenges. We're currently hiring an Account Executive to drive our New Business efforts and support our global expansion. We offer a competitive compensation package, including uncapped earnings, accelerators, and sales incentives, within a collaborative and supportive environment led by experienced executives. Join us as an Account Executive and make strategic sales contributions that will shape our company's future and open doors to leadership opportunities.

About the role

As an Account Executive you will: 

• Develop net new business relationships through inbound leads and individual outreach
• Increase penetration across divisions within existing clients, and build long-term business relationships in a mix of transactional and enterprise deals
• Receive ongoing professional development and training to help you elevate performance, grow your career, and establish a foundation for long-term sales success.
• Consult with clients on enhancing their applications and recommend SmartBear software to best meet their objectives and high priority digital transformation efforts
• Institutionalize SmartBear’s software solutions as part of customers’ software development processes

We are looking for you if you have : 

• 3+ years experience in software sales with a preference for selling into technical organizations
• Experience meeting KPI’s and have carried a quota
• Outstanding communication and presentation skills
• You are a self-starter and accountable
• Experience with LinkedIn Sales Navigator, ZoomInfo, Salesforce, and Outreach a plus
• Bachelor’s Degree or equivalent experience

Why you should join the SmartBear crew:

• You can grow your career at every level.
• We invest in your success as well as the spaces where our teams come together to work, collaborate, and have fun.
• We love celebrating our SmartBears; we even encourage our crew to take their birthdays off.
• We are guided by a People and Culture organization - an important distinction for us. We think about our team holistically – the whole person.
• We celebrate our differences in experiences, viewpoints, and identities because we know it leads to better outcomes.

Did you know?

• Our main goal at SmartBear is to make our technology-driven world a better place.
• SmartBear is committed to ethical corporate practices and social responsibility, promoting good in all the communities we serve.
• SmartBear is headquartered in Somerville, MA with offices across the world including Galway Ireland, Bath, UK, Wroclaw, Poland and Bangalore, India.
• We’ve won major industry(product and company) awards including B2B Innovators Award, Content Marketing Association, IntellyX Digital Innovator and BuiltIn Best Places to Work.

SmartBear is committed to creating an inclusive workplace for employees where all individuals are treated with respect and dignity. We are an equal opportunity employer and make employment decisions based on merit, qualifications, and business needs. We do not discriminate on the basis of race, color, religion, sex, national origin, age, gender, disability, veteran status, sexual orientation, or any other protected status under applicable laws. We are dedicated to fostering a workplace that reflects a diversity of thought and experience as well as our values of being smart, open, driven, accountable, and curious.