Job Description

Product Manager, AI Experiences

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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. Our customers include leading global organisations such as SAP, Disney, Coca-Cola, BMW, Allianz and Stryker.

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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 Product Manager to shape how users interact with AI across Checkbox.

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This role is about turning complex legal workflows into simple, trusted and useful AI-powered product experiences. You'll work across Product, Design, Engineering, Data and customer-facing teams to identify high-value AI use cases, define clear requirements and ship experiences that help legal teams work faster and with more confidence.

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This is not about adding AI sparkle to existing screens. It's about helping define how AI should meaningfully change the way legal work is raised, routed, managed and resolved.

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What You'll Do

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- Own AI-powered product experiences across legal intake, triage, matter management and workflow orchestration.
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- Work with customers and internal teams to understand legal workflows, pain points and high-value AI opportunities.
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- Translate ambiguous AI ideas into clear product problems, user journeys, requirements and success metrics.
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- Partner with Design to create AI experiences that feel intuitive, transparent and trustworthy.
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- Partner with Engineering to define how AI capabilities should behave across context, workflows, actions, review and escalation.
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- Prioritise opportunities based on customer value, technical feasibility, strategic importance and speed to market.
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- Work with Data and AI Evaluation teams to understand how AI experiences perform in production and where they need to improve.
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- Support GTM teams with clear positioning, enablement and customer understanding of new AI capabilities.
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What We're Looking For

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- Product management experience in B2B SaaS, enterprise software, workflow automation, AI products or complex productivity tools.
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- Strong product sense and the ability to turn messy customer problems into simple, valuable product experiences.
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- A practical understanding of modern AI product patterns such as assistants, copilots, RAG, agents, context, tool use and human-in-the-loop workflows.
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- Experience working closely with engineers and designers from discovery through delivery.
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- Strong customer discovery skills and the ability to separate real problems from shiny AI ideas.
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- Good judgement around trust, risk, permissions, explainability and user control in AI-powered workflows.
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- Clear communication skills and the ability to align technical and non-technical stakeholders.
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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, agentic workflows or automation tools.
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- Experience in legal tech, enterprise SaaS, no-code/low-code, workflow platforms or document-heavy products.
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- Experience with products involving approvals, permissions, auditability, compliance or high-trust decisions.
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- Experience working with data scientists, AI evaluation teams or AI observability tooling.
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Why Join Us

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You'll join at a rare moment: early enough to shape the direction, but with real customers, real usage and real enterprise problems to solve.

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You'll help define how legal teams interact with AI in their day-to-day work, and play a key role in Checkbox's next chapter as we build toward the Legal Service Hub for contemporary organisations.

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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 product area.
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- A collaborative, ambitious team building category-defining software for legal teams.
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📌 Product Manager, Agentic AI (New South Wales)
🏢 Checkbox Technology
📍 New South Wales