Director, Engineering, AI Are you passionate about transforming how legal professionals find trusted answers with AI? Join our Global Westlaw Engineering organization and help shape the future of AI-driven legal research.Westlaw helps legal professionals around the world research, analyze, and act with confidence. We are building the next generation of fiduciary-level, AI-powered legal research and workflow capabilities, and we are changing how we build software.As Director, you will lead a global organization of engineering managers, senior engineers, and vendor partners.

You will own the multi-year AI engineering strategy and its alignment with the product delivery roadmap. You will also drive the shift to AI-assisted, agent-driven development and use engineering data to guide decisions and show results.We want a technical leader with a track record of leading AI transformation, who leads by example, stays hands-on, keeps up with AI and engineering best practices, uses data to find what needs to change, and empowers teams to innovate across the organization.Set clear expectations, coach managers and engineers, and lead by example, using AI tools and engineering data in your own work.Stay close to the technical work. Work directly with senior engineers on architecture, technical direction, and hard problems to raise the technical bar across the organization.Own Engineering strategy implementation and its alignment with the product delivery roadmap.

Run it as a living plan with transparent milestones and owners, adapt quickly as priorities evolve, and recommend measures that keep engineering objectives aligned to business strategy.Lead the transformation to a mission-based operating model. Replace project-by-project handoffs with long-lived teams that own a product area, service, or customer outcome from design through production support. Define measures such as reliability, quality, delivery speed, adoption, and cost.

Help the vendor keep pace with business needs. Hold them to the same standards as internal teams for architecture, quality, security, and delivery, and measure their performance with the same data. Decide what to do in-house, with partners, or through vendors.

Balance cost, speed, capability, risk, and long-term knowledge retention.Deliver strategic projects with urgency. Partner with Product Management, UX Design, and other Technology teams. Drive the end-to-end AI lifecycle.

Hold AI and non-AI services to high standards for reliability, security, performance, and cost. Champion a DevOps-first model supported by automation, CI/CD, and infrastructure as code on AWS.Manage the project portfolio.

Operate: Run a Data-Driven, AI-Enabled Organization Provide guardrails and empower teams to use AI. Equip managers, engineers, and teams to apply AI in daily engineering work, including coding assistants, agents, code review, test automation, and quality evaluation. Provide clear guardrails for responsible use, covering security, data handling, and human review of AI-generated code and outputs.

Within those guardrails, encourage teams to experiment and adopt AI, and remove the barriers that slow them down.Make decisions with data.

Analyze

GitHub data, such as pull request cycle time, review latency, build and deployment frequency, and AI tool usage, to find bottlenecks and show where change is working.Measure the impact of AI. Track its effect on delivery speed, code quality, defect rates, and reliability. Own the economics of AI usage.

Set AI budgets, and track and optimize token consumption, inference cost, and tooling spend. Guide model selection and cost-versus-quality trade-offs, balancing them against productivity, quality, and speed.Stay on top of the AI landscape. Judge what is production-ready, bring it into your teams' practices, and grow adoption of AI/ML engineering practices and frameworks across the enterprise.Take informed risks.

A bachelor's degree in computer science, information technology, or a related field, or equivalent practical experience.10+ years in software development, including 3+ years leading AI solution development,



and 10+ years managing managers and building high-performing engineering teams in an agile environment.Experience leading managers, individual contributors, and vendor-managed teams, including scope, performance, cost, and quality. Shipping AI in production. A track record of shipping LLM-based applications, RAG, or agent workflows in production-grade software.

Cloud, DevOps, and reliability. Strong depth in cloud-native architecture on AWS, CI/CD, and infrastructure as code, and experience running mission-critical, high-availability systems.Hands-on AI tool use. Daily use of AI coding tools (e.You lead by example and have empowered managers and teams to adopt AI-assisted development, with strong practices for review, quality, and security.Data-driven leadership and AI economics.

Experience defining and analyzing metrics such as DORA, cycle time, quality, and adoption to find problems and show results. Working knowledge of token usage, inference and tooling costs, and how to measure the return on AI investment.Experience shifting team mindsets, introducing new tools and ways of working, and moving teams to mission-based, outcome-owned models with clear ownership, decision rights, and accountability.You can explain complex technical and financial trade-offs to executives and customers and align stakeholders.Experience leading globally distributed teams and restructuring an engineering organization around products, services, or customer outcomes.Agentic systems and responsible AI.

Experience shipping agentic systems in production, including evaluation, benchmarking, and monitoring, and knowledge of AI guardrails and governance.OpenAI, Anthropic) at scale, information retrieval or search systems, and standards such as Model Context Protocol (MCP).Experience with vendor selection, contract negotiation, and transitions between vendor and in-house teams.

Experience managing cloud and AI cost through FinOps or inference cost optimization.Experience building career paths for both management and technical (IC) tracks, and retaining senior technical talent.Technical background.

Strong

Python and RESTful API design skills. AWS certifications, such as Solutions Architect or DevOps Engineer, are a plus.Background in legal or other regulated, content-rich skilled domains.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.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.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.

Obsess over our Customers, Compete to Win, Challenge (Y)our Thinking, Act Rapid / 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. posting is for proactive recruitment purposes and may be used to fill current openings or future vacancies within our organization.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.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; access to Employee Assistance Program; Group Legal Identity Theft Protection benefit paid 100% by employee; Thomson Reuters complies with local laws that require upfront disclosure of the expected pay range for a position. 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.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.

Join us and help shape the industries that move society forward.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 makes reasonable accommodations for applicants with disabilities, including veterans with disabilities, and for sincerely held religious beliefs in accordance with applicable law. 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.

📌 Director, Engineering, Ai (Winnipeg)
🏢 Thomson Reuters
📍 Winnipeg