Penetration Tester Team Lead

Description

Terra Security provides agentic AI-powered continuous penetration testing aligned to code changes and evolving attack surfaces, combining a swarm of trained AI agents with human supervision for safety and control. Fortune 500 organizations trust Terra to ensure every attack surface is covered across the web, AI, internal apps, APIs, mobile, networks, and the cloud.

Terra is on track to become the next breakout cybersecurity company with $38 million raised 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.

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.

Please note that this position is for candidates based in Poland and is offered as an Independent Contractor (B2B) engagement.