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Lead Software Engineer, AI
Are you ready to shape the future of legal technology with AI? Do you thrive in ambiguous, fast-moving environments where you can build products from the ground up?
We're looking for a Lead Software Engineer to join the CoCounsel Drafting team. In this role, you'll be hands-on designing and building the systems that transform how attorneys draft, review, and refine legal documents. You'll architect LLM-powered drafting flows - orchestrating AI pipelines, prompt layers, and frontend experiences into a seamless product. You'll have the autonomy to focus on what matters: solving hard technical problems and shipping impactful products. If you're energized by ambiguity, take initiative without being asked, and love building new products - this role is for you.
Why this matters: Attorneys spend 60-70% of their time drafting documents. The tools we build are fundamentally transforming the practice of law - giving legal professionals back countless hours to focus on higher-value work for their clients. We're deeply committed to our customers' success, and we're looking for an engineer who shares that passion for making a real difference in how legal work gets done.
About the Role
In this opportunity as a Lead Software Engineer, AI, you will:
• Design and build AI-powered features for legal document drafting, working across the full stack from backend services to frontend experiences
• Architect LLM-integrated systems - designing prompt orchestration, AI pipelines, and the integration layers that connect AI capabilities to user-facing products
• Design for reliability and observability in AI systems, ensuring low-latency responses and high-quality outputs within the drafting engine
• Drive technical decisions by evaluating trade-offs, proposing architectures, and leading implementation of complex systems
• Thrive in ambiguity by proactively identifying problems, proposing solutions, and driving decisions without waiting for direction
• Collaborate cross-functionally with Product, Design, and Research to define requirements and deliver impactful features that solve real customer problems
• Mentor and elevate the team by sharing knowledge, reviewing code, and raising the bar for engineering excellence
• Embrace 0-to-1 thinking by building new capabilities from scratch - operating like a startup within a larger organization
• Own quality and delivery by writing well-tested, maintainable code and ensuring the team ships reliably
About You
You're a fit for the role of Lead Software Engineer, AI if you have the following required qualifications:
• 7+ years of software engineering experience with a track record of delivering complex, high-impact systems
• Experience building and deploying applications powered by LLMs - you understand the unique challenges of AI-integrated systems
• Proven 0-to-1 experience - you've built products from scratch, thrive in ambiguity, and know how to make decisions with incomplete information
• Strong technical foundation in our stack: C#, Python, Angular/React, and AWS
• Demonstrated proactivity - you identify what needs to be done and drive it forward without waiting to be asked
• Experience leading technical initiatives and influencing engineering direction without formal authority
• Customer-obsessed mindset - you care deeply about the impact your products have on real users
• Excellent communication skills with the ability to collaborate across engineering, product, and design
Additional preferred qualifications include:
• Experience with microfrontend (MFE) architectures
• Background in prompt engineering, vector databases, or fine-tuning language models
• Experience in legal technology, document automation, or enterprise SaaS products
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What’s in it For You?
Hybrid Work Model: We’ve adopted a flexible hybrid working environment (2-3 days a week in the office depending on the role) 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
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. For Ontario, Canada, the base compensation range for this role is $140,600 CAD - $190,600 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.
We also make reasonable accommodations for qualified individuals with disabilities and for sincerely held religious beliefs in accordance with applicable law. More information on requesting an accommodation here.
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More information about Thomson Reuters can be found on thomsonreuters.com
Who we are Thomson Reuters informs the way forward by delivering trusted content and technology that people and organizations need to make the... Read more