Senior Software Engineer, AI

Full-time | Hybrid, Sydney

Checkbox is a Series A, Sequoia-backed technology company on a mission to enable meaningful work for all.

We help in-house legal teams capture, triage, manage and resolve work through no-code automation, matter management and AI-powered legal intake.

We’re now building toward an AI-native Legal Service Hub: a new way for legal teams to manage work with systems that can understand context, reason through next steps, orchestrate workflows and keep humans in control.

We’re looking for a Senior Software Engineer, AI Experiences to help build the next generation of AI-powered product experiences across Checkbox.

You’ll work primarily with TypeScript, React and Node.js, building user-facing AI experiences, backend services and workflow capabilities that help legal teams raise, route, manage and resolve work more effectively.

This is not an AI research role. We’re looking for a strong product-minded engineer who can ship production-grade software and help turn AI concepts into reliable, useful customer experiences.

• Build AI-powered product experiences using TypeScript, React and Node.js.

• Develop frontend interfaces that make AI interactions intuitive, transparent and trustworthy.

• Build backend services and APIs that support AI workflows, orchestration, retrieval, review and escalation.

• Partner with Product and Design to turn ambiguous AI ideas into clear, shippable product experiences.

• Integrate AI capabilities into real customer workflows across legal intake, triage, matter management and automation.

• Contribute to architecture decisions across scalability, reliability, security and maintainability.

• Write high-quality, tested and observable production code.

• Mentor other engineers and contribute to strong engineering standards.

• Strong software engineering experience in SaaS, enterprise software, workflow automation or complex web applications.

• Strong TypeScript experience across frontend and backend development.

• Strong React experience and a good eye for clean, usable product experiences.

• Strong Node.js experience, including APIs, services and backend application design.

• Experience shipping production software in fast-moving product environments.

• Strong understanding of architecture, testing, observability, security and maintainability.

• Product-minded engineering judgement and clear communication.

• A pragmatic, curious and ownership-oriented mindset.

• Experience building AI-powered products, copilots, assistants or agentic workflows.

• Experience with RAG products, including retrieval, embeddings, context management, grounding or source attribution.

• Understanding of prompting strategies such as zero-shot, one-shot, few-shot and structured prompting.

• Experience integrating with LLM APIs or AI orchestration frameworks.

• Experience with legal tech, enterprise SaaS, workflow platforms or document-heavy products.

You’ll join early enough to shape the technical foundations, but with real customers, real usage and real enterprise problems to solve.

You’ll help build AI experiences that need to work in high-trust environments where reliability, context and user control genuinely matter.

• Competitive salary and equity.

• Hybrid working from our Sydney office.

• High ownership and direct impact on a strategic AI product area.

• A collaborative, ambitious team building category-defining software for legal teams.

• Yearly global events (Bali, New York, Korea)