AI Red Team Engineer

7 days ago


Ottawa, Ontario, Canada LILT Full time US$100,000 - US$120,000 per year
About LILT

AI is changing how the world communicates — and LILT is leading that transformation.

We're on a mission to make the world's information accessible to everyone, regardless of the language they speak. We use cutting-edge AI, machine translation, and human-in-the-loop expertise to translate content faster, more accurately, and more cost-effectively without compromising on brand, voice, or quality.

At LILT, we empower our teammates with leading tools, global collaboration, and growth opportunities to do their best work. Our company virtues—Work together, win together; Find a way or make one; Quicker than they expect; Quality is Job 1—guide everything we do. We are trusted by Intel Corporation, Canva, the United States Department of Defense, the United States Air Force, ASICS, and hundreds of global Enterprises. Backed by Sequoia, Intel Capital, and Redpoint, we're building a category-defining company in a $50B+ global translation market being redefined by AI.

Role Overview

LILT is seeking freelance AI Red Team experts to collaborate on projects focused on adversarial testing of AI systems — LLMs, multimodal models, inference services, RAG/embeddings, and product integrations. Your work will involve crafting prompts and scenarios to test model guardrails, exploring creative ways to bypass restrictions, and systematically documenting outcomes. You'll think like an adversary to uncover weaknesses, while collaborating with engineers and safety researchers to share findings and improve system defenses.

Key Criteria
  1. Deep Understanding of Generative AI and main models, including their underlying architectures, training processes, and potential failure modes. This includes knowledge of concepts like prompt engineering, fine-tuning, and reinforcement learning with human feedback (RLHF)

  2. Cybersecurity & Threat Modeling: Experience in cybersecurity principles, including threat modeling, vulnerability assessment, and penetration testing. Ability to identify attack vectors, simulate real-world threats, and understand the potential impact of an attack.

  3. Data Analysis & NLP: Strong analytical skills to dissect model outputs, identify subtle biases or factual errors, and recognize patterns in how the model responds to different inputs. A background in Natural Language Processing (NLP) would be highly beneficial.

  4. Ethical Hacking Mindset: A commitment to using her/his skills for defensive and security-focused purposes, adhering to a strict ethical code, and understanding the importance of responsible disclosure.

Core Requirements
  • You hold a Bachelor's or Master's Degree in Computer Science, Software Engineering, Cybersecurity, Digital Forensics or other related fields.

  • Your level of English is advanced (C1) or above

  • Adversarial thinking

  • Knowledge of vulnerabilities, common model vulnerabilities (prompt injection, prompt-history leakage, data exfiltration via RAG).

  • Experience in AI/ML security, evaluation, and red teaming, particularly with LLMs, AI agents, and RAG pipelines.

  • You are ready to learn new methods, able to switch between tasks and topics quickly and sometimes work with challenging, complex guidelines.

  • Proficient in scripting and automation using Python, Bash, or PowerShell.

  • Familiar with AI red-teaming frameworks such as garak or PyRIT.

Preferred Requirements
  • Physical-world adversarial testing

  • Experienced with containerization and CI/CD security tools, especially Docker.

  • Proficient in offensive exploitation and exploit development.

  • Skilled in reverse engineering using tools like Ghidra or equivalents.

  • Expertise in network and application security, including web application security.

  • Knowledge of operating system security concepts such as Linux privilege escalation and Windows internals.

  • Familiar with secure coding practices for full-stack development.

Benefits

Why this freelance opportunity might be a great fit for you?

  • Get paid for your expertise, with rates that can go up to $55/hour depending on your skills, experience, and project needs.

  • Take part in a part-time, remote, freelance project that fits around your primary professional or academic commitments.

  • Work on advanced AI projects and gain valuable experience that enhances your portfolio.

  • Influence how future AI models understand and communicate in your field of expertise.

Our Story

Our founders, Spence and John met at Google working on Google Translate. As researchers at Stanford and Berkeley, they both worked on language technology to make information accessible to everyone. While together at Google, they were amazed to learn that Google Translate wasn't used for enterprise products and services inside the company.The quality just wasn't there. So they set out to build something better. LILT was born.

LILT has been a machine learning company since its founding in 2015. At the time, machine translation didn't meet the quality standard for enterprise translations, so LILT assembled a cutting-edge research team tasked with closing that gap. While meeting customer demand for translation services, LILT has prioritized investments in Large Language Models, human-in-the-loop systems, and now agentic AI.

With AI innovation accelerating and enterprise demand growing, the next phase of LILT's journey is just beginning.

Our Tech

What sets our platform apart:

  • Brand-aware AI that learns your voice, tone, and terminology to ensure every translation is accurate and consistent

  • Agentic AI workflows that automate the entire translation process from content ingestion to quality review to publishing

  • 100+ native integrations with systems like Adobe Experience Manager, Webflow, Salesforce, GitHub, and Google Drive to simplify content translation

  • Human-in-the-loop reviews via our global network of professional linguists, for high-impact content that requires expert review


LILT in the News
  • Featured in The Software Report's Top 100 Software Companies

  • LILT makes it onto the Inc. 5000 List.

  • LILT's continues to be an intellectual powerhouse, holding numerous patents that help power the most efficient and sophisticated AI and language models in the industry.

  • Check out all our news on our website.

Information collected and processed as part of your application process, including any job applications you choose to submit, is subject to LILT's Privacy Policy at .

At LILT, we are committed to a fair, inclusive, and transparent hiring process. As part of our recruitment efforts, we may use artificial intelligence (AI) and automated tools to assist in the evaluation of applications, including résumé screening, assessment scoring, and interview analysis. These tools are designed to support human decision-making and help us identify qualified candidates efficiently and objectively. All final hiring decisions are made by people. If you have any concerns, require accommodations, or would like to opt-out of the use of AI in our hiring process, please let us know at

LILT is an equal opportunity employer. We extend equal opportunity to all individuals without regard to an individual's race, religion, color, national origin, ancestry, sex, sexual orientation, gender identity, age, physical or mental disability, medical condition, genetic characteristics, veteran or marital status, pregnancy, or any other classification protected by applicable local, state or federal laws. We are committed to the principles of fair employment and the elimination of all discriminatory practices.



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