Who we are At Twilio, we're shaping the future of communications, all from the comfort of our homes. We deliver innovative solutions to hundreds of thousands of businesses and empower millions of developers worldwide to craft personalized customer experiences. As we continue to revolutionize how the world interacts, we're acquiring new skills and experiences that make work feel truly rewarding. Your career at Twilio is in your hands. We use Artificial Intelligence (AI) to help make our hiring process efficient. That said, every hiring decision is made by real Twilions! Join the team as Twilio's next Senior Offensive Security Engineer About the job This position is needed to The Senior OffSec Engineer will be responsible for the day-to-day execution of penetration tests and contributing to larger Red Team campaigns. You move beyond simple scanning to manual exploitation and are beginning to automate your workflows. Responsibilities In this role, you'll: 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. Required: Experience: 3–5 years in offensive security, penetration testing, or a high-volume bug bounty background and track record of finding high/critical vulnerabilities in complex environments. 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 Burp Suite professional, Nmap, Metasploit, Wireshark etc... and AI security tools such as LangChain, TensorFlow for adversarial testing, 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 Python, C++, and scripting for creating custom offensive tooling that avoids signature-based detection. Certifications: Possession of advanced industry certifications such as OSCP, OSEP, OSWE, GXPN or similar Telecom expertise is preferred
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\nRole: Actively devise and execute sophisticated, multi-stage attack campaigns that emulate the tactics, techniques, and procedures (TTPs) of relevant threat actors. Identify and exploit vulnerabilities across the organisation's digital and physical landscapes, including networks, applications, facilities, and personnel. Conduct covert red team operations, including network penetration testing, application security assessments, social engineering, and physical security breach simulations. Lead and participate in purple team exercises, working collaboratively with the blue team to analyse attack paths, test detection capabilities, and improve incident response playbooks in real-time. Assess the effectiveness of remediation efforts by re-testing identified vulnerabilities and attack paths after fixes have been implemented. Develop custom tooling and scripts to automate and enhance attack simulations. Create detailed post-engagement reports that clearly document findings, articulate business risk, and provide actionable recommendations for improving security posture. Act as the resident subject matter expert on offensive security and threat actor methodologies.
\nRequirements: 3+ years of experience in an offensive security role (e.g., Red Teaming, Penetration Testing). Proven experience in planning and executing covert red team operations from reconnaissance to objective completion. A deep understanding of attacker TTPs and frameworks like MITRE ATT&CK. Proficient in at least one scripting language, such as Python, for tooling and automation. Hands-on experience with common offensive security tools (e.g., Cobalt Strike, Metasploit, Burp Suite, custom implants). Strong analytical and problem-solving skills with a creative and unconventional mindset. Ability to work both independently and collaboratively in a team environment. Excellent written and oral communication skills, with the ability to articulate complex technical risks to both technical and non-technical audiences.
\nBonus: Any relevant certifications such as OSCP, OSCE, or OSEP. Experience with physical security assessments or social engineering campaigns. Previous experience building and running a red team program.
\nWhat we offer: All our positions offer a compensation package that includes equity and robust benefits. Base pay is just one component of Astranis’s total rewards package. Your compensation also includes a significant equity package via incentive stock options, high-quality company-subsidized healthcare, disability and life insurance, 401(k) retirement planning, flexible PTO, and free on-site catered meals.
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\nYou will plan and execute red team operations, penetration tests, and attack simulations across our cloud infrastructure, web and mobile applications, AI/ML pipeline, and corporate environment,finding real vulnerabilities before adversaries do and working directly with engineering teams to drive remediation.
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