Penetration Tester

About the role

Cliffside Cybersecurity is seeking a Penetration Tester to act as a modern offensive security consultant. You will evaluate how web applications, APIs, cloud services and AI‑enabled platforms behave under realistic attack scenarios, moving beyond checklist‑driven testing.

Key responsibilities

• Conduct comprehensive penetration tests on web applications, APIs, cloud environments and identity platforms.
• Design and execute attack scenarios that include AI‑driven workflows, chat‑bots, copilots and autonomous agents.
• Identify technical vulnerabilities, behavioural flaws, abuse paths and unintended outcomes in AI systems.
• Simulate real‑world attackers by chaining vulnerabilities across services and validating defensive controls such as WAFs, rate limiting and bot protection.
• Document findings with clear business risk articulation and contribute to the evolution of testing methodologies and tooling.

Required profile

• Proven experience in web, API, infrastructure and cloud penetration testing.
• Ability to scope, execute and deliver end‑to‑end engagements independently.
• Background in adversary simulation or red‑team operations.
• Comfort operating in ambiguous environments and adapting methodologies on the fly.
• Strong interest in AI‑enabled applications and modern attack surfaces.

Required skills

• Penetration testing
• Web application security
• API security testing
• Cloud security assessment
• Infrastructure security testing
• AI/ML system testing (prompt injection, policy bypass, data leakage)
• Red teaming / adversary simulation
• WAF, rate limiting and bot protection validation