Senior Security Researcher - Red Team (Contract)

As a Senior Security Researcher (Red Team), you will help Pindrop proactively identify and exploit weaknesses across product, cloud, and AI-powered systems so we can strengthen defenses before adversaries do. This role blends hands-on offensive security, GenAI attack simulation, security engineering, and operational partnership with blue-team, product, and AI/ML stakeholders.

Responsibilities:

• Design and execute red team operations against Pindrop’s GenAI systems, LLM pipelines, RAG architectures, autonomous agents, APIs, SaaS products, and cloud environments, simulating real-world attacks across both traditional and AI-specific attack surfaces.
• Conduct adversarial testing focused on prompt injection, indirect prompt attacks, jailbreaking, model extraction, training-data poisoning, data leakage, inference abuse, and unauthorized output manipulation.
• Use deepfake generation, voice synthesis, and related spoofing techniques to test and attempt to defeat Pindrop’s voice authentication and deepfake detection capabilities, helping identify model robustness and detection gaps.
• Develop novel attack chains that combine GenAI vulnerabilities with infrastructure, application, identity, and API weaknesses to create realistic end-to-end threat scenarios.
• Plan and execute full-scope penetration tests and support bug bounty efforts across Pindrop’s web applications, APIs, SaaS products, and AWS/GCP environments using commercial and open-source offensive tooling.
• Perform architecture reviews, security code reviews, and threat modeling with emphasis on vulnerabilities introduced by AI/ML components, model integrations, and LLM-facing services.
• Build automation for offensive security workflows, testing, compliance checks, alerting, and reporting using Python or similar scripting languages, including AI-native attack tooling where useful.
• Partner closely with SecOps and security engineering to improve detections, tune response workflows, and translate red team findings into practical remediation and defensive improvements.
• Stay current on GenAI security research, adversarial ML techniques, evolving threat intelligence, and relevant regulatory developments, then apply those insights to Pindrop’s security program.

Requirements:

• 3+ years of hands-on penetration testing and red team experience across SaaS applications, cloud infrastructure, APIs, and web applications.
• Demonstrable experience attacking GenAI or LLM-based systems, including prompt injection, jailbreaking, indirect prompt attacks, model extraction, or adversarial input generation.
• Hands-on experience with deepfake tools, voice synthesis, or audio/visual spoofing technologies in an offensive or research context.
• Strong proficiency with offensive security tooling such as Burp Suite, OWASP ZAP, Nmap, Metasploit, Cobalt Strike, or equivalent frameworks.
• Experience configuring and operating SAST and DAST tools and integrating them into CI/CD pipelines.
• Proficiency in at least one scripting or programming language, with Python strongly preferred, for custom attack tooling and workflow automation.
• Familiarity with AI-specialized security tools or frameworks such as Garak, PyRIT, Claude Security, or similar adversarial ML tooling.
• Strong understanding of cloud security architecture, container security, API security, and common security standards including ISO 27001/27002, NIST, CIS, PCI DSS, OWASP, and SOC 2.

Benefits:

• Competitive compensation, including equity for all employees
• Unlimited Paid Time Off (PTO)
• Remote-first culture