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About the Role
We are looking for a hands-on Principal Engineer to act as the senior technical authority across Checkbox’s product engineering streams. This role is accountable for making, recording, and governing key technical decisions that shape our future-state product architecture, ensuring it remains sound, coherent, and safe as we scale. You will influence through judgment, clarity, and working code, not people management.
Responsibilities
- Own key architecture decisions across Checkbox’s product engineering streams, including high-consequence one-way-door decisions
- Define, document, and govern the future-state product architecture
- Ensure architecture remains coherent across product streams, Platform, Data Engineering, QA, Enterprise IT, and other technology teams
- Identify, design, and help build force-multiplier initiatives that help engineering teams move faster and ship higher-quality software
- Contribute directly to production releases and set the technical bar through working code
- Drive engineering decisions through data, feedback loops, and measurable quality signals rather than opinion alone
- Embed fitness functions, architecture measures, and technical feedback loops into how product engineering works
- Partner closely with the Data Engineering function on the data and AI reference architecture
- Ensure tenancy, security, and compliance are designed into systems from the start
- Work closely with Product, Customer Success, and Sales so architecture decisions reflect real customer and commercial needs
- Support teams in making pragmatic technical trade-offs between speed, scale, quality, security, and maintainability
Requirements
- Significant experience as a Principal Engineer, Staff Engineer, Architect, or senior technical leader in a modern SaaS environment
- Deep systems expertise across product engineering, platform architecture, distributed systems, and modern cloud-native software
- Strong track record of making and governing high-impact architecture decisions across multiple teams or product areas
- Proven ability to design and ship force-multiplier technical initiatives that improve engineering velocity, quality, or reliability
- Comfortable contributing to production systems while also setting broader technical direction
- Strong understanding of tenancy, security, compliance, and data isolation in enterprise SaaS environments
- Experience working closely with platform, data, QA, infrastructure, or enterprise IT teams
- Strong product and customer judgment, with the ability to connect technical decisions to commercial and customer outcomes
- Ability to influence through credibility, clarity, and working code rather than formal authority
- Excellent communication skills, with the ability to bring technical and non-technical stakeholders along
- Pragmatic, hands-on, and comfortable operating in a fast-moving scale-up environment
Skills
- AI-native products
- Agentic systems
- Workflow automation
- Enterprise legal technology
- Architecture across multiple product streams
- Multi-product SaaS ecosystem
- Systems relying on context, retrieval, eventing, integrations, or AI-enabled workflows
- AI or data reference architecture
- Engineering fitness functions
- Architectural decision records
- Technical standards
- Quality measures
Location
- Sydney
Work Type
- Permanent
- Hybrid
Experience Level
- Principal Engineer
- Staff Engineer
- Architect
- Senior technical leader
Benefits
- Competitive salary
- Hybrid working with team days in our Sydney CBD office
- High ownership over architecture decisions that shape Checkbox’s product and engineering future
- Direct impact across product engineering, platform, data and AI systems
- Opportunity to help scale an AI-first SaaS platform used by leading enterprise legal teams
- Personal learning and development budget
- Flexible leave policy
- Expense policy and salary sacrifice options
- CBD start-up hub with snacks, drinks, premium coffee and team socials
- Company-wide social events and annual off-sites
About the Company
- Checkbox is a Series A, Sequoia-backed technology start-up with a mission to enable meaningful work for all.
- We are building an AI-first platform that is transforming how in-house legal teams operate, from how work enters legal through to how it is understood, routed, managed and resolved.
- Our customers include leading in-house legal teams at companies such as SAP, Coca-Cola, Allianz, BMW, Elastic and Stryker.
- We are now expanding beyond workflow automation into AI-powered intake, matter management, triage and work orchestration.
- Our vision is to become the Legal Service Hub for modern organisations, responsible for how legal work is raised, allocated, managed and resolved.
- As we scale our product, engineering organisation and AI capabilities, we need our architecture to stay coherent, secure and built for the future.
Equal Opportunity
- Transparent, flat culture where questions and feedback are welcomed