Penetration Tester Team Lead

Terra Security is on track to become the next breakout cybersecurity company. As the winner of the 2025 AWS + CrowdStrike + NVIDIA Cybersecurity Startup Accelerator, Terra has earned recognition from some of the most influential names in modern security. The company has raised $38 million to date, including a $30 million Series A led by Felicis Ventures with participation from Dell Technologies Capital, Silicon Valley CISO Investments (SVCI), SYN Ventures, LAMA Partners, Underscore VC, and Capital One Ventures.

Terra’s platform is powered by a swarm of fine-tuned AI agents with human-in-the-loop oversight, delivering unmatched efficiency, accuracy, and continuous attack surface coverage. It runs thousands of best-in-class tests and crafts tailored, exploit-driven assessments based on each organization's unique business logic and risk profile.

Summary 

As a Penetration Tester Team Lead, you will play a pivotal role in our global expansion by building and leading a new penetration testing team in Europe. You will blend deep technical expertise with leadership to bridge the gap between automated AI efficiency and high-level human ingenuity. This is a unique opportunity to shape a high-performance team within a company that is fundamentally changing how security assessments are performed.

What You’ll Do

• Help recruit, mentor, and manage a world-class team of penetration testers across Europe, fostering a culture of technical excellence and continuous learning.
• Lead complex web application and API penetration tests, providing "human-in-the-loop" oversight to our AI-driven assessments.
• Work closely with our engineering team to integrate AI tools into daily automation workflows, enhancing the "swarm" with real-world exploit logic.
• Review and finalize high-quality security reports, ensuring technical findings are accurate and remediation guidance is actionable for diverse stakeholders.
• Partner with customers to communicate the business impact of security findings and guide them through complex remediation strategies.
• Stay ahead of the threat landscape by developing and refining internal testing methodologies and custom exploitation techniques.

Requirements

• 5+ years of hands-on experience in Web Application and API Penetration Testing.
• Proven experience managing, mentoring, or leading technical security teams.
• Deep knowledge of the OWASP Top 10, common attack methodologies, and exploitation techniques.
• Proficiency with TCP, HTTP, and various client-side/server-side languages.
• Expert-level experience with Burp Suite, Caido, and other industry-standard security testing utilities.
• High-level English proficiency (fluent written and verbal) with a knack for writing clear, high-quality technical reports.

Advantage

• Strong coding skills (Python, Go, or Bash) for scripting, automation, or secure software development.
• Practical experience using AI tools to enhance security workflows and automation.
• Experience engaging directly with clients to translate technical risk into business logic.
• Professional certifications such as CREST, OSWA/OSWE, or GPEN.