AI Application Penetration Tester

Contract Length: 12 Months (40 hours/week)
Work Environment: Hybrid (3 days onsite, 2 days remote)
Locations: 1. Charlotte, NC 2. Minneapolis, MN 3. Irving, TX
Employment Type: W2 Contract
We're supporting an enterprise security organization that is rapidly expanding its Security for AI initiative. With hundreds of new GenAI use cases emerging across the business, this team is scaling its penetration testing capabilities to assess AI-powered applications, LLMs, agentic workflows, and machine-learning pipelines.
This role focuses on offensive security testing for modern AI ecosystems, including prompt-driven attack surfaces, model manipulation vulnerabilities, and AI-specific adversarial behaviors. If you're an experienced offensive security engineer with deep AppSec fundamentals and strong Python development skills - this is an opportunity to work on cutting-edge adversarial AI testing at enterprise scale.

Key Responsibilities

AI/GenAI Penetration Testing

• Perform manual and automated penetration tests on:
  • GenAI applications
  • Large Language Model (LLM) integrations
  • Agentic AI workflows
  • ML pipelines and AI-augmented APIs
• Evaluate emergent AI attack types such as:
  • Prompt injection & indirect prompt exploits
  • Model evasion & inference manipulation
  • Abusing vector databases
  • Bypassing guardrails, safety layers, and filtering
  • Adversarial input generation

Offensive Security Operations

• Conduct testing using:
  • BurpSuite
  • Custom Python tooling
  • Adversarial AI tools & frameworks
• Test against OWASP Top 10 and OWASP LLM Top 10 risks.
• Execute manual exploitation to validate automated scanner findings.

Application Security Collaboration

• Partner with engineering teams to define test scope and gather system details.
• Identify application-layer vulnerabilities and provide practical remediation guidance.
• Communicate attack paths and risks clearly to both technical and business partners.

Documentation & Reporting

• Produce detailed POCs, exploit walkthroughs, and technical root-cause analysis.
• Document vulnerabilities, exploitation processes, and remediation recommendations.
• Deliver high-quality written penetration test reports on time.

Contribution to Enterprise AI Security

• Support threat models, red team simulations, governance reviews, and assessments across hundreds of GenAI use cases annually.
• Help reduce a significant backlog of AI-related testing needs and mature the organization's AI security posture.

Required Skills & Qualifications

GenAI / AI Security

• Hands-on experience testing GenAI applications, LLM integrations, ML pipelines, or agentic systems.
• Ability to evaluate emerging AI-specific attack surfaces and adversarial behaviors.

Offensive Security (6-8+ years)

• Strong background in:
  • Application penetration testing
  • Manual exploitation
  • Automated scanning configuration
  • Security tool usage and validation methods

Application Security Expertise

• Deep understanding of application-layer vulnerabilities.
• Experience reviewing modern distributed architectures, API flows, and security controls.

Python Development (4-5 years)

• Build automation and exploit scripts for:
  • Payload generation
  • Attack orchestration
  • API-based testing
  • LLM/AI bypass attempts
• Ability to analyze model outputs programmatically.

Communication & Reporting

• Experience working with stakeholders to define scope and testing requirements.
• Ability to clearly communicate vulnerabilities, risks, and remediation paths.
• Strong written communication skills for final report delivery.

Nice-to-Have Skills

• Experience with Garak or similar adversarial AI tools.
• Relevant certifications such as:
  • OSWE
  • OSWA
  • BSCP
  • GWAPT

Employee Value Proposition

This is a rare opportunity to perform cutting-edge adversarial testing on AI systems used across a large enterprise. You'll gain exposure to emerging GenAI technologies, influence security standards, and help shape the future of AI safety within a complex environment.
As the organization rapidly deploys AI solutions, this role offers substantial impact, visibility, and long-term growth potential in the AI security domain.

Why the Position Is Open

The organization is expanding its AI security program to keep pace with the rapid adoption of GenAI across the business. With hundreds of annual assessments required, new engineers are being added to support penetration tests, threat models, and governance reviews for AI-powered applications.

External-Facing Summary

We're seeking an experienced AI Application Penetration Tester to perform advanced offensive security testing on Generative AI and LLM-powered applications. This role focuses on identifying vulnerabilities unique to modern AI systems, performing adversarial testing, and providing clear, actionable remediation guidance to engineering teams.
Job Type & Location
This is a Contract position based out of Irving, TX.
Pay and Benefits
The pay range for this position is $80.00 - $85.00/hr.
Eligibility requirements apply to some benefits and may depend on your job classification and length of employment. Benefits are subject to change and may be subject to specific elections, plan, or program terms. If eligible, the benefits available for this temporary role may include the following: Medical, dental & vision Critical Illness, Accident, and Hospital 401(k) Retirement Plan - Pre-tax and Roth post-tax contributions available Life Insurance (Voluntary Life & AD&D for the employee and dependents) Short and long-term disability Health Spending Account (HSA) Transportation benefits Employee Assistance Program Time Off/Leave (PTO, Vacation or Sick Leave)
Workplace Type
This is a hybrid position in Irving,TX.
Application Deadline
This position is anticipated to close on Feb 9, 2026.
>About TEKsystems:
We're partners in transformation. We help clients activate ideas and solutions to take advantage of a new world of opportunity. We are a team of 80,000 strong, working with over 6,000 clients, including 80% of the Fortune 500, across North America, Europe and Asia. As an industry leader in Full-Stack Technology Services, Talent Services, and real-world application, we work with progressive leaders to drive change. That's the power of true partnership. TEKsystems is an Allegis Group company.

The company is an equal opportunity employer and will consider all applications without regards to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.

About TEKsystems and TEKsystems Global Services

We're a leading provider of business and technology services. We accelerate business transformation for our customers. Our expertise in strategy, design, execution and operations unlocks business value through a range of solutions. We're a team of 80,000 strong, working with over 6,000 customers, including 80% of the Fortune 500 across North America, Europe and Asia, who partner with us for our scale, full-stack capabilities and speed. We're strategic thinkers, hands-on collaborators, helping customers capitalize on change and master the momentum of technology. We're building tomorrow by delivering business outcomes and making positive impacts in our global communities. TEKsystems and TEKsystems Global Services are Allegis Group companies. Learn more at TEKsystems.com.

The company is an equal opportunity employer and will consider all applications without regard to race, sex, age, color, religion, national origin, veteran status, disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.