Director Software Development Jobs in Toronto, ON

Manager, Software Engineering

Content Tools CoCounsel Legal Integrations

Overview of the Role

CoCounsel Legal Integrations is seeking a Manager, Software Engineering to lead the engineering team responsible for building, operating, and evolving Thomson Reuters' Content Tools platform. Content Tools are the purpose-built APIs and capabilities that give AI agents precise, reliable access to TR's most valuable legal content - including case law, statutes, regulations, citations, and Practical Law materials. These tools are mission-critical infrastructure: the bridge between TR's authoritative content assets and the AI-powered products - such as CoCounsel Legal - that depend on them.

The Manager owns the full engineering lifecycle for Content Tools: design, implementation, testing, deployment, and ongoing operations. Equally important, this leader will navigate a distributed development model in which tools are built and contributed by multiple teams across the organization. The Manager is responsible for establishing governance, design standards, and contribution workflows that keep the ecosystem coherent as it grows - while serving as the primary engineering accountability point for tool quality, reliability, and developer experience.

This is a people leadership role managing a team of approximately 10 engineers. The successful candidate brings strong platform thinking, a collaborative leadership style, and deep credibility in building API-first systems - ideally in domains where information quality and retrieval precision carry high stakes.

About the Role

In this position, you will provide:

Tool Engineering & Technical Leadership

• Own the end-to-end engineering roadmap for Content Tools - spanning tool design and implementation, CLI and SDK exposure, CI/CD pipelines, evaluation infrastructure, and cloud operations - balancing new capability delivery with rigorous quality and reliability standards

• Drive an API-first, contract-driven approach to tool development: every tool ships with a versioned CLI contract, schema, and clear ownership metadata that makes it discoverable and usable by consuming teams without direct engineering involvement

• Establish and enforce the patterns, templates, and contribution standards that allow distributed teams to build and contribute tools consistently - including review workflows, quality gates, namespace governance, and guidance on when to create new tools versus extend existing ones

• Lead the build-out of the information retrieval (IR) evaluation framework, ensuring every tool is validated against representative datasets before release and that performance regressions are caught automatically in CI/CD

• Champion full-stack operational ownership: the team defines, builds, tests, deploys, and operates what it ships - including on-call rotations, SLO definitions, incident response, and health monitoring for production tool services

• Partner closely with TR Labs and CoCounsel Engineering teams to ensure content tools meet the interface requirements of agentic workflows - covering tool invocation patterns, result provenance,

• Oversee platform infrastructure, including cloud services (AWS), observability tooling, rate limiting, caching strategies, and multi-tenant access controls that protect licensed content

Distributed Development Governance

• Serve as the engineering accountability point for the Content Tools ecosystem as a whole - not just the tools your team builds directly, but the standards and guardrails that govern contributions from partner teams across the organization

• Define and maintain contribution workflows, architectural review criteria, and consistency checks that prevent capability duplication and ensure interoperability across a growing tool catalog

• Manage tool lifecycle policies, including deprecation, migration support, versioning strategies, and breaking-change processes - communicating proactively with consuming teams to minimize disruption

• Build and maintain a centralized tool registry with machine-readable descriptions, usage guidance, and performance characteristics - making the tool ecosystem discoverable and self-service for agent developers

• Establish shared development infrastructure - common libraries, boilerplate generators, mock services, and local development environments - that makes it easy for any team to build tools correctly

Team Management

• Build and lead a team of approximately 10 software engineers (including Senior and Staff levels), managing hiring, onboarding, performance, and professional development with a focus on deep technical ownership

• Develop engineers who combine strong software fundamentals with domain fluency in information retrieval, content APIs, and agentic system design - engineers who are proud to own their work from first commit to production dashboard

• Foster a culture of empowered ownership where engineers have the autonomy to define problems, the authority to make sound technical calls, and the accountability to carry work through to reliable production operations

• Translate complex content technology concepts for non-technical stakeholders - making the value and trade-offs of Content Tools investments legible to product managers, business leaders, and partner teams

• Model and reinforce AI-assisted development as a team norm: more than 50% of code written with AI assistance is the target, not a stretch goal

Strategic Delivery

• Define and maintain engineering processes for a team that both builds shared tool infrastructure and delivers production content capabilities - ensuring rigorous testing, code review, and continuous evaluation of tool quality through offline IR grading pipelines and online signals

• Establish platform health and developer experience benchmarks - including tool reliability SLOs, client onboarding time-to-value, IR evaluation pass rates, and tool invocation accuracy - and use them to drive continuous improvement

• Evaluate and integrate emerging tool protocols (including MCP support) and retrieval patterns, with a clear-eyed view of production-readiness and operational implications

• Cultivate strong working relationships with Labs, Product, and CoCounsel Engineering - engaging early in agentic workflow design to ensure content tools are shaped to the access patterns agents actually need

• Collaborate across the organization to align the Content Tools roadmap with business priorities in CoCounsel Legal Next, Westlaw, and the broader TR product portfolio

About You

You're an ideal fit if you have:

Required Experience

• Bachelor's or Master's degree in Computer Science, Engineering, or a related field

• 6+ years of software engineering experience, with at least 2 years in a technical leadership or engineering management role

• Demonstrated experience designing and operating API-first systems consumed by multiple teams, with a product mindset toward developer experience and internal customer satisfaction

• Proficiency in Python and strong software engineering fundamentals, API design, testing strategy (unit, integration, and IR/evaluation), and CI/CD practices

• Experience building and governing shared platform infrastructure in a distributed development model - including contribution standards, versioning policies, and cross-team coordination

• Familiarity with information retrieval concepts - including precision/recall trade-offs, hybrid search, citation networks, and document retrieval patterns - sufficient to make sound architectural decisions and partner effectively with scientists

• Proven ability to lead teams that own their production systems end-to-end, including on-call responsibilities, SLO management, and incident response

• Strong leadership skills: experience in agile methodologies, excellent communication, and the ability to build alignment across engineering, product, and science teams

• Awareness of AI ethics, content licensing considerations, and responsible deployment of retrieval systems

Preferred Experience

• Experience building tools or APIs for agentic AI systems, including familiarity with tool protocols such as MCP (Model Context Protocol) or similar

• Background in legal technology, knowledge management, or other high-stakes information retrieval domains where provenance, accuracy, and entitlement enforcement are critical

• Hands-on experience with search and retrieval infrastructure (e.g., Elasticsearch, Vespa, OpenSearch) and the trade-offs between semantic and structured search

• Experience with evaluation frameworks for retrieval systems, including dataset design, IR metrics (Precision, Recall, NDCG, etc.), and CI/CD integration of quality gates

• Familiarity with content access control, policy-based entitlements, and licensing enforcement in multi-tenant environments

• Experience operationalizing tooling for LLM-powered workflows, including prompt engineering, tool description design, and agent invocation patterns

#LI-SM2

This posting is for proactive recruitment purposes and may be used to fill current openings or future vacancies within our organization.

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.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. For any eligible US locations, unless otherwise noted, the base compensation range for this role is $118,400 USD - $219,800 USD. 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 speci...