Job Description

Senior Software Engineer, AI

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Full-time | Hybrid, Sydney

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The Company

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

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

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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.

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The Role

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

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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.

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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.

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What You'll Do

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- Build AI-powered product experiences using TypeScript, React and Node.js.
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- Develop frontend interfaces that make AI interactions intuitive, transparent and trustworthy.
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- Build backend services and APIs that support AI workflows, orchestration, retrieval, review and escalation.
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- Partner with Product and Design to turn ambiguous AI ideas into clear, shippable product experiences.
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- Integrate AI capabilities into real customer workflows across legal intake, triage, matter management and automation.
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- Contribute to architecture decisions across scalability, reliability, security and maintainability.
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- Write high-quality, tested and observable production code.
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- Mentor other engineers and contribute to strong engineering standards.
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What We're Looking For

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- Strong software engineering experience in SaaS, enterprise software, workflow automation or complex web applications.
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- Strong TypeScript experience across frontend and backend development.
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- Strong React experience and a good eye for clean, usable product experiences.
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- Robust Node.js experience, including APIs, services and backend application design.
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- Experience shipping production software in fast-moving product environments.
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- Strong understanding of architecture, testing, observability, security and maintainability.
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- Product-minded engineering judgement and clear communication.
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- A pragmatic, curious and ownership-oriented mindset.
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Nice to Have

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- Experience building AI-powered products, copilots, assistants or agentic workflows.
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- Experience with RAG products, including retrieval, embeddings, context management, grounding or source attribution.
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- Understanding of prompting strategies such as zero-shot, one-shot, few-shot and structured prompting.
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- Experience integrating with LLM APIs or AI orchestration frameworks.
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- Experience with legal tech, enterprise SaaS, workflow platforms or document-heavy products.
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Why Join Us

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

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

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Benefits

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- Competitive salary and equity.
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- Hybrid working from our Sydney office.
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- High ownership and direct impact on a strategic AI product area.
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- A collaborative, ambitious team building category-defining software for legal teams.
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- Yearly global events (Bali, New York, Korea)
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📌 Senior Software Engineer, AI (New South Wales)
🏢 Checkbox
📍 New South Wales