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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