Principal Software Engineer

About Checkbox

Checkbox is a Series A technology start-up backed by Sequoia, focused on enabling meaningful work across in-house legal teams. The company is developing an AI-first platform that transforms legal operations, including intake, matter management, triage, and workflow orchestration. Its clientele includes prominent legal teams from SAP, Coca-Cola, Allianz, BMW, Elastic, and Stryker. Checkbox aspires to become the Legal Service Hub for modern organizations, overseeing legal work initiation, allocation, management, and resolution.

Role Overview

The Principal Software Engineer will serve as the senior technical authority guiding Checkbox's product engineering streams. This role involves owning and governing pivotal architecture choices, particularly irreversible "one-way-door" decisions critical to product evolution. Acting as a technical leader, the position demands maintaining architectural coherence and security throughout company growth, ensuring key decisions are documented and adhered to rather than relying on tribal knowledge.

Responsibilities

• Oversee major architectural decisions affecting the product engineering across multiple streams, including high-stakes irreversible choices.
• Define, document, and enforce the envisioned future-state architecture of Checkbox’s products.
• Maintain consistent and secure architecture across product teams, platform, data engineering, QA, and enterprise IT divisions.
• Conceive and contribute to engineering initiatives that accelerate development and enhance software quality.
• Contribute actively to production releases and uphold high technical standards through exemplary code.
• Use data-driven approaches, feedback loops, and measurable quality indicators to guide engineering decisions.
• Integrate fitness functions, architecture metrics, and technical feedback mechanisms into development processes.
• Collaborate closely with Data Engineering on AI and data reference architectures.
• Embed tenancy, security, and compliance considerations into system design from the outset.
• Partner with Product, Customer Success, and Sales teams to align architectural decisions with customer and business needs.
• Support teams in balancing trade-offs between speed, scalability, quality, security, and maintainability.

Candidate Profile

• Extensive background as a Principal Engineer, Staff Engineer, Architect, or comparable senior technical leader in SaaS environments.
• Profound expertise in product engineering, platform architecture, distributed systems, and cloud-native technologies.
• Demonstrated history of making and managing impactful architectural decisions spanning multiple teams or product areas.
• Success in designing and implementing technical initiatives that enhance engineering speed, quality, or reliability.
• Comfortable contributing hands-on to production while defining overarching technical directions.
• Strong awareness of tenancy models, security protocols, compliance standards, and data isolation in enterprise SaaS.
• Experience collaborating with platform, data, QA, infrastructure, and enterprise IT groups.
• Good product sense and understanding of customer needs, connecting technical decisions with commercial outcomes.
• Ability to influence through technical credibility, clarity, and delivery rather than formal authority.
• Excellent communication skills to align diverse technical and non-technical stakeholders.
• Pragmatic, hands-on approach suitable for a dynamic and fast-growing scale-up environment.

Additional Qualifications (Bonus)

• Experience with AI-native products, agentic systems, workflow automation, or enterprise legal technology.
• History of defining architecture across multiple product lines or multi-product SaaS ecosystems.
• Expertise designing systems involving context, retrieval, eventing, integrations, or AI-enabled workflows.
• Collaborative experience with data engineering on AI or data reference architectures.
• Introduction of engineering fitness functions, architectural decision records, technical standards, or quality controls.
• Exposure to high-growth stage companies such as Series A or Series B funded startups.

Benefits

• Competitive salary package
• Hybrid working arrangement with mandatory team days in Sydney CBD office
• Significant influence over architectural decisions shaping the future of Checkbox’s platform
• Direct impact on engineering, platform, data, and AI system development
• Opportunity to contribute to scaling an AI-first SaaS platform serving top-tier enterprise legal teams
• Personal development and learning budget
• Flexible leave policies
• Expense reimbursement and salary sacrifice options
• Startup hub location in Sydney CBD with snacks, beverages, premium coffee, and regular team events
• Company-wide social occasions and annual off-sites
• Open and transparent culture encouraging feedback and questions