Principal Data Engineer
HybridSydney, New South Wales, Australia
Job Summary
Own the data and AI reference architecture across Checkbox's product ecosystem, defining base data sources, intelligence services, and retrieval layers that power agentic workflows. Architect secure, tenant-isolated access patterns for customer, matter, and workflow data while establishing principles for storage, retrieval, and compliance. Lead the tier-one Data team, mentoring engineers on pragmatic systems design and building shared data capabilities that reduce duplication across product streams. Partner closely with Product, Engineering, and Platform teams to ensure new features generate reliable, governed data for analytics and AI agents.
Required Qualifications
- Significant experience as a senior data engineer, principal data engineer, data architect, staff engineer or similar technical leadership role
- Proven experience building data and context foundations that power AI products in production
- Strong experience designing data architectures across transactional, operational, analytical and AI-ready systems
- Deep understanding of modern data platform patterns, including data contracts, event-driven architecture, ingestion, transformation, observability, lineage and governance
- Strong understanding of AI data patterns such as retrieval systems, embeddings, semantic modelling, vector search, knowledge graphs, context engineering or agentic workflows
- Experience working with multi-tenant SaaS systems where data segregation, tenancy and access control matter
- Ability to make pragmatic architecture decisions and select the right tool or pattern for each problem
- Strong judgement around buy-vs-build decisions across data infrastructure, retrieval, orchestration and AI platform layers
- Comfortable leading technical direction while still building, reviewing and shipping
- Experience mentoring engineers or leading small technical teams
- Strong communication skills and ability to work closely with product engineering streams, platform teams and senior engineering leadership
- Comfortable operating in a fast-moving environment where systems are being built, scaled and refined at the same time
Desired Qualifications
- Experience working on AI agents, agentic workflows, GenAI platforms or AI-native SaaS products
- Experience designing MCP or API surfaces for data and context access
- Experience with legal tech, workflow automation, enterprise SaaS or document-heavy products
- Experience with AWS-based data and platform infrastructure
- Experience with event-driven systems, queues, Pub/Sub patterns or streaming architectures
- Experience with data security, compliance, auditability and enterprise customer requirements
- Experience growing a small data function from early foundations into a scalable team
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