AI Penetration Tester (Contract)
DATAMTX LLC
WHO WE ARE
Datamtx ( / 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.
(Multipler 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.
$86.8k - $198k
Red Team Penetration TesterThe Opportunity: We’re mission accelerators... ...technology. As a penetration tester, you'll play a pivotal role in... ..., and experience, as well as contract-specific affordability and... ...and prevent fraud.Candidate AI Usage PolicyAI is a part of our...Contract workFull timePart timeWork at officeLocal areaRemote work$86.8k - $198k
Penetration TesterThe Opportunity:Conduct testing and analysis to identify... ...Artificial Intelligence (AI) systems and their ecosystemsBachelor... ...), HTB Certified Penetration Tester Specialist (CPTS),... ..., and experience, as well as contract-specific affordability and organizational...Contract workFull timePart timeWork at officeLocal areaRemote work$86.8k - $198k
Red Team Penetration TesterThe Opportunity: We’re mission accelerators... ...technology. As a penetration tester, you'll play a pivotal role in... ..., and experience, as well as contract-specific affordability and... ...and prevent fraud.Candidate AI Usage PolicyAI is a part of our...Contract workFull timePart timeWork at officeLocal areaRemote work$86.8k - $198k
Enterprise Cybersecurity Penetration TesterThe Opportunity: As a member of the Booz Allen internal... ...competencies, and experience, as well as contract-specific affordability and organizational... ...identity and prevent fraud.Candidate AI Usage PolicyAI is a part of our daily work...Contract workFull timePart timeLocal areaRemote work- ...position supporting a federal or government contract, candidates must be U.S. citizens and... ...: We’re looking for an experienced Penetration Tester to join our security team and lead... ...phishing and lateral movement activities, AI‑enabled testing, and PCI‑DSS engagements...Contract workRemote work
- ...Packetlabs is hiring a Penetration Tester for expert-level application security testing across... ...approach across Web, API, Mobile, and AI/LLM . Requirements Customer-first... ...posting does not constitute an employment contract or guarantee of continued employment....Contract workSecond jobRemote workFlexible hours
$60 - $100 per hour
...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,... ...for SaaS and cloud environments. Conduct penetration testing and adversarial threat modeling...Contract workHourly payRemote work$86.8k - $198k
...education, knowledge, skills, competencies, and experience, as well as contract-specific affordability and organizational requirements. The... ...picture to verify your identity and prevent fraud.Candidate AI Usage PolicyAI is a part of our daily work at Booz Allen, and we...Contract workFull timePart timeWork at officeLocal areaRemote work- ...clear understanding of the rapidly evolving AI-driven threat landscape—including AI-powered red teaming, automated penetration testing, and novel attack vectors. The analyst... ...level Mid-Senior level Employment type Contract Job function Information Technology Industries...Contract workWork from home
- Plan and execute penetration tests across web, mobile (iOS & Android), API, cloud-native/containerized, and AI/LLM-integrated applicationsAssess AI/ML and generative AI-powered features for risks such as prompt injection, insecure output handling, training data poisoning...Temporary workLocal area
- Vulnerability Management Analyst (AI Training) About the Role We're looking for experienced... .... Organization : Alignerr Type : Hourly Contract Location : Remote Commitment : 10-40... ...in threat intelligence, red teaming, or penetration testing Familiarity with cloud...Contract workHourly payOngoing contractFreelanceRemote workWorldwideFlexible hours
$104k - $166k
ResponsibilitiesPeraton is currently seeking to hire an experienced Penetration Tester for its Federal Strategic Cyber Group. Location: Chandler,... ..., as well as geographic location and business and contract considerations. Depending on the position, employees may be...Contract workCurrently hiringShift work- ...Contract Hudson Yards, NYC/Remote Key Responsibilities Vulnerability Analysis & Risk Assessment Review vulnerabilities identified through AI-based SAST, SCA, and related application security tools. Evaluate vulnerabilities beyond vendor-assigned severity...Contract workRemote work
$86k - $138k
ResponsibilitiesPeraton is seeking an experienced Cyber Penetration Tester to become part of Peratons’ Federal Strategic Cyber programs. Location... ..., as well as geographic location and business and contract considerations. Depending on the position, employees may be...Contract workFlexible hoursShift work$100 - $110 per hour
...: Vulnerability Management Analyst Location: Remote Duration: Contract Job ID: SYFJP00001328 Job Overview The Security Analyst III, specializing... ...for validating reports and analyzing trends. Familiarity with AI-enabled productivity or analysis tools, coding assistants, and...Contract workFull timeRemote work$120 - $160 per hour
...resilience and regulatory readiness. This is an opportunity for a penetration tester who enjoys tackling varied engagements, communicating... ...etc.). Benefits This position offers a flexible, remote contract opportunity for penetration testers looking to work on...Contract workHourly payRemote workFlexible hours- ...missions worldwide.Job DescriptionOverviewSOSi is seeking a Penetration Tester III to support proactive cyber defense activities in alignment... ...requested to work evenings and weekends to meet program and contract needs.Working at SOSiAll interested individuals will receive...Contract workWork at officeWorldwideMonday to FridayWeekend workAfternoon shift
- ...processes and decisions that people can rely on.Job: Penetration TesterRole description:As a Penetration Tester, you will be responsible for identifying,... ..., the salary for this position starts from 40,000.Contract Type: Permanent ContractThe actual compensation package...Contract workPermanent employmentFull timeSummer workWork at officeRemote work
- ...Florida / Miami area Work Model: Hybrid / Onsite Engagement: Contract with potential Contract-to-Direct Hire Duration: 6–12 months... ...Citizen and Green Cards candidates only. Help Secure How AI Connects Into the Enterprise We are looking for a Senior...Contract work
- ...agenda-setting, reporting, and action item tracking. Operationalizes AI governance standards (NIST AI RMF, ISO/IEC 42001), including AI... ...control requirements for SaaS, cloud, and AI providers; ensure contract provisions address security, privacy, SLAs, and right-to-audit....Contract workWork at office
$120.5k - $210k
...services.Verizon Cybersecurity (VCS) is looking for an Application Penetration Tester to join our Enterprise Pen Test team. You’ll be joining a... ...organization as needed.Helping to lead the definition of Pen Test (with AI) strategy and standards to further enhance the company’s...Full timeTemporary workPart timeWork experience placementRemote workWork from homeShift work- ...organization. Work you'll do This role is responsible for providing penetration testing services through a combination of technology and manual... ..., processes, and standards documentationLeveraging AI and LLM-based tools and prompt engineering, using both established...Visa sponsorship
$128.65k - $214.34k
...goals.Job Overview:As a member of the Cyber Security team, an AVP Penetration Tester of Offensive Security will be responsible for helping with the... ...with Security Architects during the SDLC processes for LLM / AI to make recommendations and offer our ability to identify...Full timeWork from home$110k - $160k
...Analytics is seeking a highly motivated Penetration Tester to join our cybersecurity team in... ...analytics, and Artificial Intelligence (AI) platform providing civilian and military... ...With a proven track record in federal contracting, we deliver tailored, high-impact solutions...Full timeWork at office- ...what you excel at—all from Day One.Job DescriptionThe Senior Penetration Tester will lead advanced offensive security assessments across mobile... ...applications, APIs, web platforms, cloud environments, and emerging AI-enabled technologies. This role is responsible for identifying...Full timeWork experience placementLocal area3 days per week
$85 - $105 per hour
...Job Description Senior GCP Architect - Contract \n \n Harnham is partnering with a leading consulting firm supporting a major gaming client on a large-scale cloud transformation and AI infrastructure programme. \n \n \n Role: Senior GCP Architect \n...Contract workLong term contractRemote work$110k - $150k
...an experienced professional to join our team! As a Red Team Penetration Tester, you will be responsible for conducting penetration testing... ...well as alignment with our corporate compensation plan and contract specific requirements. The projected annual compensation...Contract workTemporary workCasual workFlexible hours- ...requirements and hold a relevant forensics certification. This is a contract to hire opportunity. Applicants must be willing and able to work... ...advised that Eliassen Group utilizes artificial intelligence (AI) tools as part of its initial application screening and hiring...Contract workHourly payLocal areaTrial periodShift workDay shift
$95k - $105k
SS&C is a leading provider of mission-critical, AI-powered technology and services empowering financial services and healthcare organizations... ...policy and procedures supporting overall compliance including; contract, state/regulatory requirementsLeverage technology expertise to...Contract workOngoing contractFull timeRemote workWorldwide- ...while you advance your career. Join GDIT as an Ethical Hacker/Penetration Tester Sr Principal and build an impactful career in enterprise IT, collaborating... ...our people are at the center of everything we do. Growth: AI-powered career tool that identifies career steps and learning...Work experience placement
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to AI Penetration Tester (Contract). Be the first to apply!
- vulnerability management analyst United States
- vulnerability analyst United States
- ethical hacker United States
- penetration tester United States
- entry level penetration tester
- web penetration tester
- vulnerability management analyst
- web application penetration tester
- licensed penetration tester
- ethical hacker work from home






