Job Opportunity Posted today Updated 28 Sep 2026

AI Penetration Tester (Contract)

Job Description

WHO WE ARE

Datamtx (www.datamtx.com / formerly Datamatics) established in 1993 is globally HQ‘d in Atlanta with a stellar history supporting both Tier 1 and 2 ERP / MES projects including: S/4HANA, JDE, Oracle Cloud ERP, Peoplesoft, Deltek, Infor (M3 / S3 / Syteline / LN / Factory Track / MacPac XE / LX, XA, CPQ), IFS, Deltek, Blackbaud, Ellucian Banner, D365, SysPro, Epicor, Plex, BlackLine, etc..

Our ERP / MES projects cover the gamut of typical implementation but we also support bespoke projects and specialty staffing needs covering: data cleanse, customizations, lift & shift, cloud & data migrations, M&A consolidations, Hypercare and Day 1 support. We are also globally partnered with some of some of the Top Accounting, Advisory and Audit firms.


(Multiple Remote Engagements)

Flexible Hours / Part-time Acceptable


AI Penetration Tester (Contract)

DataMTX is seeking AI Penetration Testers to support multiple client engagements through a our partnerships with global audit and tax firms. This role involves assessing the security of AI-powered applications, LLM chatbots, AI agents, Copilot implementations, and multi-agent systems. The ideal candidate has experience with both traditional application/API penetration testing and emerging AI security testing techniques.


Required Skills

  • Experience conducting penetration testing engagements
  • Knowledge of OWASP LLM Top 10 (required)
  • Experience testing one or more of:
  • LLM Chatbots
  • AI Agents
  • Copilot Implementations
  • Multi-Agent Systems
  • Familiarity with AI attack techniques such as prompt injection, jailbreak testing, sensitive data leakage, system prompt extraction, and agent/tool abuse

Preferred Frameworks

  • OWASP GenAI Security Project
  • MITRE ATLAS
  • NIST AI RMF
  • AI Red Teaming Methodologies

Tool Experience Hands-on experience with at least two of the following:

  • Burp Suite
  • Caido
  • Garak
  • PyRIT
  • Microsoft Counterfit
  • Inspect AI
  • Promptfoo
  • OpenAI Evals
  • Giskard
  • Custom attack tooling

Engagement Type

  • Contract / Consulting
  • Remote
  • Multiple AI and application security assessment projects available


Nice to Have: OSCP, GPEN, GWAPT, OSWE, AI Security or Red Teaming certifications.

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