InfoSec Penetration Tester for AI Training

SaidGig; New York (NY); Remote; USD 83,000 - 138,000; Part time

Job summary

SaidGig is seeking a remote contract cybersecurity expert to help train next-generation AI systems by delivering high-quality security input for enterprise SaaS projects. You will design red-team workflows, conduct penetration testing across Microsoft 365, Google Workspace, Slack, GitHub, and Snowflake, and provide clear written and verbal feedback to improve defenses in real-world SaaS environments.

You will conduct penetration testing and adversarial threat modeling across Microsoft 365,

Qualifications

• Hands-on red teaming, pen testing, app security, cloud security, or security engineering.
• Enterprise SaaS security expertise including identity, RBAC, and data governance.
• Experience evaluating security for Microsoft 365, Google Workspace, Slack, GitHub, and Snowflake.
• Ability to assess adversarial ways AI and SaaS platforms could be exploited or compromised.
• Strong written and verbal communication; proven real-world impact on security projects.
• Experience in AI or LLM security is a bonus.

Responsibilities

• Design red-team workflows and adversarial scenarios for SaaS and cloud environments.
• Conduct penetration testing and adversarial threat modeling across Microsoft 365, Google Workspace, Slack, GitHub, and Snowflake.
• Serve as a senior reviewer, assessing the quality and depth of red-team exercises and deliverables.
• Identify and document AI-agent misuse and manipulation risks, including prompt injection, privilege escalation, data exfiltration, and destructive actions.
• Provide practical input on security controls, policies, and detection strategies for real-world SaaS environments.
• Collaborate with cybersecurity professionals and provide detailed written and verbal feedback on findings and improvements.
• Create adversarial scenarios for benchmarking that reflect current threats and attack methods.

Skills

Red Teaming

Penetration Testing

Application Security

Cloud Security

Security Engineering

AI / LLM Security

Job description

Role Overview

Apply hands‑on cybersecurity expertise to help train next-generation AI systems through high‑quality, real‑world security input. This remote contract role supports an enterprise SaaS project, with no prior AI experience required.

Key Responsibilities

• Design comprehensive red‑team workflows and adversarial scenarios for SaaS and cloud environments.
• Conduct penetration testing and adversarial threat modeling across Microsoft 365, Google Workspace, Slack, GitHub, and Snowflake.
• Serve as a senior reviewer, assessing the quality and depth of red‑team exercises and deliverables.
• Identify and document AI‑agent misuse and manipulation risks, including prompt injection, privilege escalation, data exfiltration, and destructive actions.
• Provide practical input on security controls, policies, and detection strategies for real‑world SaaS environments.
• Collaborate with cybersecurity professionals and provide detailed written and verbal feedback on findings and improvements.
• Create adversarial scenarios for benchmarking that reflect current threats and attack methods.

Qualifications

• Extensive hands‑on experience in red teaming, penetration testing, application security, cloud security, or security engineering.
• Deep understanding of enterprise SaaS security, including identity, RBAC and permissions, and data governance.
• Security evaluation experience with Microsoft 365, Google Workspace, Slack, GitHub, and Snowflake.
• Ability to assess adversarial ways AI and SaaS platforms could be exploited or compromised.
• Strong written and verbal communication skills for explaining complex security issues and recommended remediations.
• A demonstrated record of practical, real‑world impact on security projects.
• Experience in AI or LLM security, or adversarial testing of agent‑based systems, is a bonus.

Work Terms

Remote contract engagement.

Compensation

$60 to $100 per hour.