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Added 9 mins ago
UO
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Thomson Reuters

Sr. Legal AI Prompter, Evaluator

Toronto, ON, Canada

Full-time

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Job details

Job type: Full-time
Apply by: Dec 9, 2026
Posting language: English
Posted: Nov 9, 2026

Original job description

Sr. Legal AI Prompter / Evaluator

Job Description

Sr. Legal AI Prompters / Evaluators are responsible for improving CoCounsel Legal by writing and refining prompts, skills, and agent configurations; experimenting with large language models (LLMs), including Thomson, our proprietary LLM; and evaluating the results. They partner closely with specialized legal subject matter experts (SMEs), software engineers, and data scientists to make sure our products deliver accurate, legally sound outputs that legal professionals can trust. As senior members of the team, they take a leading role in the hands-on development of LLM-driven solutions, design and run experiments to find out what works, and help raise the team’s capabilities. The ideal candidate is an experienced, practiced lawyer with a passion for technology and a strong understanding of emerging technologies in the legal profession, who can think critically about AI risks and opportunities and translate legal expertise into practical, high-quality AI outputs.

Key Responsibilities

Create, test, and refine prompts, skills, and agent configurations for CoCounsel Legal to ensure accurate, legally sound, and contextually appropriate responses
Experiment with Thomson and other LLMs on legal tasks, comparing results to inform which model best fits each use case
Build gold-standard datasets with SMEs, coordinate evaluations, and design evaluation schemes, including rubrics, metrics, success criteria, and LLM-as-judge prompts, to test model outputs and inform launch readiness decisions
Write and run scripts, experiments, and automated tests that ensure quality and consistency over large datasets and time periods
Monitor production performance, analyze failure modes and identify where in the pipeline they originate (prompting, tooling, retrieval, or content), and provide strategic feedback to software engineers and data scientists
Collaborate with software engineers, data scientists, and cross-functional teams as they integrate LLMs into multi-step systems, and evaluate the feasibility and potential impact of new product ideas
Engage with legal professionals, industry leaders, and internal stakeholders to gather insights and validate product concepts, and stay informed about developments in legal technology and LLMs
Mentor colleagues and draft guidance materials, reusable prompts, and best-practice documentation on getting the most out of LLMs

Required Qualifications

Juris Doctor degree or equivalent law degree and bar admission in a US or Canadian jurisdiction
5-7 years of combined experience, including at least 2-3 years of legal practice, with the remaining years in related work such as collaborating with software engineers, building or testing products, applying generative AI, or writing code
Proven expertise applying generative AI, including prompt engineering and evaluating model outputs, and an understanding of how LLMs work and where they fail
Proficiency working in a Python code base and using Git, including writing, modifying, and debugging Python scripts, calling LLMs through code (e.g., OpenAI, Anthropic, Gemini), and using coding agents to build and iterate on that work
Excellent communication and collaboration skills, with the ability to work effectively with legal SMEs and across functions

Preferred Qualifications

Have substantial experience working with and testing legal products and technology, including online legal research and practice tools
Have hands-on experience designing evaluations, such as rubrics, human grading frameworks, or LLM-as-judge prompts
Are familiar with agentic and RAG systems, including how retrieval, tool use, and prompting each affect output quality
Are a self-starter who is comfortable with ambiguity and learns new tools and models quickly

Replacement: This position is open due to an existing vacancy to support our evolving business needs.

What’s in it For You?

Hybrid Work Model: We’ve adopted a flexible hybrid working environment for our office-based roles while delivering a seamless experience that is digitally and physically connected.
Flexibility & Work-Life Balance: Flex My Way is a set of supportive workplace policies designed to help manage personal and professional responsibilities, whether caring for family, giving back to the community, or finding time to refresh and reset. This builds upon our flexible work arrangements, including work from anywhere for up to 8 weeks per year, empowering employees to achieve a better work-life balance.
Career Development and Growth: By fostering a culture of continuous learning and skill development, we prepare our talent to tackle tomorrow’s challenges and deliver real-world solutions. Our Grow My Way programming and skills-first approach ensures you have the tools and knowledge to grow, lead, and thrive in an AI-enabled future.
Industry Competitive Benefits: We offer comprehensive benefit plans to include flexible vacation, two company-wide Mental Health Days off, access to the Headspace app, retirement savings, tuition reimbursement, employee incentive programs, and resources for mental, physical, and financial wellbeing.
Culture: Globally recognized, award-winning reputation for inclusion and belonging, flexibility, work-life balance, and more. We live by our values: Obsess over our Customers, Compete to Win, Challenge (Y)our Thinking, Act Fast / Learn Fast, and Stronger Together.
Social Impact: Make an impact in your community with our Social Impact Institute. We offer employees two paid volunteer days off annually and opportunities to get involved with pro-bono consulting projects and Environmental, Social, and Governance (ESG) initiatives.
Making a Real-World Impact: We are one of the few companies globally that helps its customers pursue justice, truth, and transparency. Together, with the professionals and institutions we serve, we help uphold the rule of law, turn the wheels of commerce, catch bad actors, report the facts, and provide trusted, unbiased information to people all over the world.

Our use of AI within the recruitment process Thomson Reuters utilizes Artificial Intelligence (AI) to support parts of our global recruitment process. Unless you opt-out, our AI system will assess the information provided by you and compare it to the requirements listed for the role, and present the result to our recruitment personnel for further review. The AI system acts as a supporting tool, but there is always a human making the decision if you will be considered for the role.

In the United States, Thomson Reuters offers a comprehensive benefits package to our employees. Our benefit package includes market competitive health, dental, vision, disability, and life insurance programs, as well as a competitive 401k plan with company match. In addition, Thomson Reuters offers market leading work life benefits with competitive vacation, sick and safe paid time off, paid holidays (including two company mental health days off), parental leave, sabbatical leave. These benefits meet or exceeds the requirements of paid time off in accordance with any applicable state or municipal laws. Finally, Thomson Reuters offers the following additional benefits: optional hospital, accident and sickness insurance paid 100% by the employee; optional life and AD&D insurance paid 100% by the employee; Flexible Spending and Health Savings Accounts; fitness reimbursement; access to Employee Assistance Program; Group Legal Identity Theft Protection benefit paid 100% by employee; access to 529 Plan; commuter benefits; Adoption & Surrogacy Assistance; Tuition Reimbursement; and access to Employee Stock Purchase Plan.

Thomson Reuters complies with local laws that require upfront disclosure of the expected pay range for a position. The base compensation range varies across locations. Eligible office location(s) for this role include one or more of the following: New York City, San Francisco, Los Angeles, and/or Irvine, CA; McLean, VA; Washington, DC. The base compensation range for the role in any of those locations is $137,900 USD - $256,100 USD. For any eligible US locations, unless otherwise noted, the base compensation range for this role is $119,700 USD - $222,300 USD. For Ontario, Canada, the base compensation range for this role is $126,000 CAD - $176,000 CAD. Base pay is positioned within the range based on several factors including an individual’s knowledge, skills and experience with consideration given to internal equity. Base pay is one part of a comprehensive Total Reward program which also includes flexible and supportive benefits and other wellbeing programs. This role may also be eligible for an Annual Bonus based on a combination of enterprise and individual performance.

About Us

Thomson Reuters informs the way forward by bringing together the trusted content and technology that people and organizations need to make the right decisions. We serve professionals across legal, tax, accounting, compliance, government, and media. Our products combine highly specialized software and insights to empower professionals with the data, intelligence, and solutions needed to make informed decisions, and to help institutions in their pursuit of justice, truth, and transparency. Reuters, part of Thomson Reuters, is a world leading provider of trusted journalism and news.

We are powered by the talents of 26,000 employees across more than 70 countries, where everyone has a chance to contribute and grow professionally in flexible work environments. At a time when objectivity, accuracy, fairness, and transparency are under attack, we consider it our duty to pursue them. Sound exciting? Join us and help shape the industries that move society forward.

As a global business, we rely on the unique backgrounds, perspectives, and experiences of all employees to deliver on our business goals. To ensure we can do that, we seek talented, qualified employees in all our operations around the world regardless of race, color, sex/gender, including pregnancy, gender identity and expression, national origin, religion, sexual orientation, disability, age, marital status, citizen status, veteran status, or any other protected classification under applicable law. Thomson Reuters is proud to be an Equal Employment Opportunity Employer providing a drug-free workplace.

Thomson Reuters makes reasonable accommodations for applicants with disabilities, including veterans with disabilities, and for sincerely held religious beliefs in accordance with applicable law. If you reside in the United States and require an accommodation in the recruiting process, you may contact our Human Resources Department at HR.Leave-Expert@thomsonreuters.com. Disability accommodations in the recruiting process may include things like a sign language interpreter, making interview rooms accessible, providing assistive technology, or other relevant accommodations. Please note this email is not intended for general recruitment questions and we will promptly respond to inquiries regarding accommodations. More information on requesting an accommodation here.

Learn more on how to protect yourself from fraudulent job postings here.

More information about Thomson Reuters can be found on thomsonreuters.com

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More about this job

Responsibilities

Develop and refine prompts, skills, and agent configurations for CoCounsel Legal, and experiment with LLMs to evaluate accuracy and suitability for legal tasks. Build evaluation datasets and frameworks, monitor production quality, collaborate with technical and legal teams, and mentor colleagues through guidance and best-practice documentation.

Requirements

Requires a Juris Doctor or equivalent law degree, bar admission in the United States or Canada, and 5–7 years of combined experience, including at least 2–3 years in legal practice. Candidates must have hands-on generative AI and prompt-engineering experience, understand LLM capabilities and limitations, and be proficient with Python codebases and Git.

Skills

Prompt Engineering
Generative AI
Large Language Models
Python
Git
Model Evaluation
Legal Expertise
Experiment Design
Dataset Development
Automated Testing
Failure Analysis
Agentic Systems
Retrieval-Augmented Generation
Cross-Functional Collaboration
Technical Communication
Mentoring

Benefits

Flexible Vacation
Mental Health Days
Health Insurance
Dental Insurance
Vision Insurance
Disability Insurance
Life Insurance
Retirement Savings Plan
Tuition Reimbursement
Employee Incentive Programs
Headspace App Access
Work-Life Benefits
Parental Leave
Sabbatical Leave
Fitness Reimbursement
Employee Assistance Program
Flexible Spending Account
Health Savings Account
Employee Stock Purchase Plan
Adoption and Surrogacy Assistance
Commuter Benefits
Paid Volunteer Days

Visa sponsorship

Not detected in the job text

Keywords

CoCounsel Legal
Thomson
Large Language Models
Generative AI
Prompt Engineering
Python
Git
OpenAI
Anthropic
Gemini
Coding Agents
Legal Technology
Legal Research
Agent Configurations
Agentic Systems
Retrieval-Augmented Generation
Evaluation Rubrics
Human Grading
LLM-as-Judge
Gold-Standard Datasets
Automated Testing
Model Performance Monitoring
Failure Mode Analysis
Software Engineering
Data Science
Legal Subject Matter Experts
Experiment Design
Prompting
Retrieval
Tool Use

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