Senior Manager of Offensive Security

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.

Our dedication to remote-first work, and strong culture of connection and global inclusion means that no matter your location, you’re part of a vibrant team with diverse experiences making a global impact each day. 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!

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Join the team as Twilio’s next Senior Manager of Offensive Security.

As the Senior Manager of Offensive Security and Red Teaming, you will lead an elite team of ethical hackers and security penetration testers dedicated to proactively uncovering and mitigating vulnerabilities across the enterprise and our products. You are a technical expert and a strategic leader. You will design and oversee sophisticated adversary emulation exercises that challenge our defenses, ensuring that our security team and overall security posture are prepared for real-world threats.

In this role, you’ll:

• →Strategic Leadership: Develop and execute a multi-year roadmap for offensive security, including red teaming, penetration testing, bug bounty, and vulnerability research.
• →Adversary Emulation: Design and lead full-scope red team engagements that simulate Advanced Persistent Threats (APTs) to test detection and response capabilities.
• →Program Management: Oversee the end-to-end lifecycle of offensive engagements, from initial scoping and Rules of Engagement (RoE) to final reporting.
• →Purple Teaming: Facilitate collaborative "Purple Team" exercises with Detection and Response (TDR) to improve detection logic and incident response playbooks.
• →Executive Communication: Translate complex technical findings into actionable business risk assessments for C-suite executives and Board members.
• →Team Mentorship: Recruit, retain, and develop a high-performing team of offensive security engineers, providing technical guidance and career coaching.
• →Vulnerability Management Integration: Partner with vulnerability management, product, and engineering  to ensure that findings from offensive tests are prioritized and remediated effectively.
• →Tooling & Automation: Oversee the development of custom scripts, payloads, and C2 (Command and Control) frameworks to enhance the team’s stealth and efficiency.
• →Adversarial AI Testing: Conduct specialized threat modeling for AI-native applications, focusing on the OWASP Top 10 for LLMs and MITRE ATLAS (Adversarial Threat Landscape for AI Systems).
• →AI attacks and mitigations: Design and execute manual and automated Prompt Injection & Jailbreaking to bypass model guardrails, system prompts, and safety filters.
• →Regulatory Compliance: Ensure all offensive activities align with legal, ethical, and regulatory standards (e.g., GDPR, SOC2, PCI-DSS).
• →Threat Intelligence Integration: Incorporate current Cyber Threat Intelligence (CTI) into attack scenarios to ensure they reflect the latest real-world TTPs (Tactics, Techniques, and Procedures).
• →Third-Party Oversight: Manage relationships and quality control for external security consultancy firms performing third-party penetration tests.
• →Research & Development: Encourage and lead research into emerging technologies to identify future attack vectors.
• →Cross-Functional Collaboration: Work closely with Product and Engineering teams to bake security into the Software Development Life Cycle (SDLC) through testing and assessments

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!

• Experience: Minimum of 10+ years in cybersecurity, with at least 5 years specifically in offensive security roles and 2+ years in a leadership or management capacity.
• Technical Expertise: Deep knowledge of security frameworks like the MITRE ATT&CK framework, Cyber Kill Chain, and advanced exploitation techniques (e.g., AD, cloud, and applications attacks).
• Certifications: Possession of advanced industry certifications such as OSCP, OSEP, OSWE, GXPN or similar
• Infrastructure Knowledge: Proficient in attacking and defending diverse environments including AWS/Azure/GCP, Kubernetes, and hybrid-cloud architectures.
• Hands-on AI Testing: Proven experience in automating red teaming for GenAI and proficiency in using AI offensive tools like PyRIT, Prompfoo, Xbow or Counterfit to build and stage AI powered attacks
• Tooling Proficiency: Advanced experience with red team and penetration testing tools such as Cobalt Strike, Burp Suite Pro, Metasploit, BloodHound, and Sliver.
• Programming Skills: Strong ability to code or script in Python, PowerShell, Go, or C++ for exploit development and task automation.
• Analytical Thinking: Proven ability to connect individual vulnerabilities into complex attack chains that demonstrate significant business impact.
• Ethical Integrity: A flawless record of ethical conduct and the ability to handle extremely sensitive access and information with total discretion.

• Telecom expertise is preferred

This role will be remote, but is not eligible to be hired in CA, CT, NJ, NY, PA, WA.

We prioritize connection and opportunities to build relationships with our customers and each other. For this role, you may be required to travel occasionally to participate in project or team in-person meetings.

We like to solve problems, take initiative, pitch in when needed, and are always up for trying new things. That's why we seek out colleagues who embody our values — something we call Twilio Magic. Additionally, we empower employees to build positive change in their communities by supporting their volunteering and donation efforts.

So, if you're ready to unleash your full potential, do your best work, and be the best version of yourself, apply now! If this role isn't what you're looking for, please consider other open positions.

Twilio is proud to be an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, consistent with applicable federal, state and local law. Qualified applicants with arrest or conviction records will be considered for employment in accordance with the Los Angeles County Fair Chance Ordinance for Employers and the California Fair Chance Act. Additionally, Twilio participates in the E-Verify program in certain locations, as required by law.