Senior Director Software Engineering Jobs in Toronto, ON

Senior Director, Software Engineering - Customer Content Platform

CoCounsel Agent Context

Do you want to build the infrastructure that makes enterprise AI feel effortless to legal professionals? Can you lead engineering teams tackling the hard problems of file management, ingestion at scale, compliance, and data migration? This is the kind of work that is invisible when done well yet critical to every user interaction, and it puts you at the foundation ofCoCounsel.

As Senior Director of Software Engineering, Customer Content Platform, you will own the engineering vision and execution for howCoCounselstores, organizes, secures, and delivers the documents and data that legal professionals work with every day, and how that content is made available to AI agents. You will lead teams that own their systems end to end, from design and build through production operations: the file and workspace platform, a high-throughput ingestion and orchestration pipeline built to scale toward millions of files per workspace, a connectors platform that reaches customers' existing document systems, compliance capabilities including BYOK, and the migration of existing customers to the next generation ofCoCounsel.

About the Role

In this opportunity as Senior Director, Customer Content Platform, you will:

• Set the customer content platform engineering strategy:define the technical direction for file management, workspace organization, sharing controls, ingestion, and compliance infrastructure, in alignment withCoCounsel'sproduct roadmap and Thomson Reuters' data-security standards.

• Lead and develop engineering managers and their teams:build a high-performance, inclusive culture across a globally distributed organization. Own workforce planning, hiring, talent assessment, performance differentiation, coaching, succession planning, and career development at all levels.

• Instill end-to-end ownership:ensure your teams own their services across the full lifecycle, from design and build through deployment and day-to-day production operations, including on-call, incident response, operational metrics, and continuous reliability improvement (a "you build it, you run it" culture).

• Own the file and workspace platform:including sharing models, workspace roles and permissions, permission inheritance from external systems, workspace lifecycle management, and compliance features such as BYOK and data residency, ensuring enterprise-grade security for legal data.

• Deliver ingestion and file processing at scale:own a reliable, event-driven ingestion and orchestration pipeline engineered toward our goal of supporting millions of files per workspace, with broad file-type and large-file support and asynchronous background processing. Design for multi-tenant isolation, resource quotas, noisy-neighbor fairness,throughputand latency SLOs, and resilient failure handling (graduated retries with backoff, poison-message classification, and dead-letter quarantine with safe replay).

• Build andoperatethe connectors platform:enableCoCounselto connect to third-party document management systems such asiManage, NetDocuments, SharePoint, HighQ, Box, Dropbox, and Google Drive, including agent-native access to customer content, while faithfully preserving source-system permissions and structure.

• Make content agent-ready:ensure ingested and connected content is parsed, indexed, and exposed to agent workflows, retrieval, and semantic search, partnering on the interfaces (including MCP-style access) that letagentsreason over customer documents reliably and securely.

• Drive the migration to the next generation ofCoCounsel:own the engineering work that safely and reliably migrates existing customer workspaces, file archives, and storage backends to the next-generation platform, with zero data loss, data-integrity guarantees, and minimal customer disruption.

• Partner across theCoCounselengineering pillar:work closely with the Agent Core/Intelligence, Application Experience, AI Platform, Document Understanding, and Enterprise Search Platform teams to ensure file and data infrastructure meets the needs of agent workflows and user experiences.

• Champion engineering quality, reliability, and compliance:establishsecurity-by-design, reliability, observability, and data-handling standards appropriate for a regulated legalenvironment, andcontribute to Thomson Reuters' broader infrastructure and compliance goals.

About You

You'rea fit for this role if your background includes:

• 12+ years of software engineering experience, including 5+ years in senior engineering leadership managing engineering managers and globally distributed teams.

• A proventrack recordbuilding file management, storage, or data-infrastructure platforms at enterprise scale, ideally distributedstorageand high-throughput, event-driven processing systems.

• A strong backend anddistributed-systemsengineering foundation: distributed storage, APIs, asynchronous and queue-based processing, multi-tenancy, security, and platform reliability and observability.

• Experienceoperatingmulti-tenant systems at scale, including resource isolation, quotas, workload prioritization, and noisy-neighbor mitigation.

• A track recordof leading teams thatoperatewhat they build, with full-lifecycle ownership including production on-call, SLOs, and incident response.

• A deep understanding of enterprise data-compliance requirements: data residency, BYOK, access controls, permission models, audit logging, and regulatory frameworks.

• Experience designing and executing large-scale data migrations between enterprise systems, with strong attention to data integrity and customer continuity.

• Demonstrated ability to lead complex, cross-functional engineering programs involving multiple teams and stakeholders, and to set direction under ambiguity.

• A clear, confident communicator with both technical teams and senior business stakeholders.

Additional Preferred Qualifications

• Background in legal technology or enterprise document management systems (e.g.,iManage, NetDocuments, SharePoint), including matter-centric security and ethical walls.

• Experience building enterprise file-connector and integrationplatforms, andintegrating with third-party DMS APIs at scale.

• Experience delivering data and content infrastructure that powers AI or LLM agent workflows, such as retrieval and semantic search, indexing pipelines, or agent-native access patterns (e.g., MCP).

• Familiarity with legal and public-sector compliance requirements such as BYOK, FedRAMP, or CJIS.

• Experience buildingdata-migrationpipelines for large-scale SaaS enterprise environments.