Job Description

Senior Technical Product Manager, AI Products n

Full-time | Hybrid | Sydney

The Company n

Checkbox is a Series A B2B legal technology company building foundational tools for enterprise legal teams to better own, manage and resolve legal work at scale.

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Our platform combines modern SaaS workflow tooling with agentic AI-native product experiences, helping legal teams capture, triage, route, manage and complete work with greater visibility, speed and control.

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We are building toward a new category of Legal Service Hub: the system that helps in-house legal teams understand demand, orchestrate workflows and deliver better outcomes across the business.

The Role n

We are looking for a Senior Technical Product Manager, AI Products to shape how AI is used across Checkbox’s product suite.

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This role is about turning complex legal workflows into simple, trusted and useful AI-powered product experiences. You will own high-impact AI product areas across intake, triage, matter management, workflow orchestration and agentic automation.

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You will work closely with Product, Design, Engineering, Data, AI Evaluation and customer-facing teams to identify high-value AI use cases, define product behaviour and ship experiences that help legal teams work faster, with more confidence and less manual effort.

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

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You should also be highly comfortable working in an AI-native product development environment, using AI tools to improve discovery, specification, analysis, prototyping, delivery and iteration.

What You’ll Own n

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- Own AI product strategy and execution across legal intake, triage, matter management and workflow orchestration
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- Identify high-value AI opportunities through customer discovery, internal expertise and product usage data
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- Translate ambiguous AI ideas into clear product problems, user journeys,



requirements and success metrics
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- Define how AI capabilities should behave across context, reasoning, actions, review, escalation and handoff
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- Shape agentic workflows, including skills, subagents, tool use, task boundaries and human-in-the-loop moments
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- Partner with Design and Engineering to create AI experiences that are intuitive, transparent, technically feasible and production-ready
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- Work with Data and AI Evaluation teams to understand AI performance in production and improve quality over time
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- Define evaluation criteria for AI-powered workflows, including accuracy, usefulness, grounding, latency, cost, safety and user trust
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- Help shape how Product, Design and Engineering use AI throughout the product development lifecycle
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- Support GTM teams with clear positioning, enablement and customer understanding of new AI capabilities
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About You nn
- Senior product management experience in B2B SaaS, enterprise software, workflow automation, AI products or complex productivity tools
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- Strong technical fluency and confidence working closely with Engineering, Data and AI Evaluation teams
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- Practical understanding of AI product patterns such as assistants, copilots, RAG, agents, context, tool use, skills and human-in-the-loop workflows
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- Comfortable reasoning about model strengths, model weaknesses, failure modes, evals, prompt behaviour, retrieval quality and AI product reliability
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- Experience working in an AI-native SDLC, using AI tools to amplify product discovery, specification writing, analysis, prototyping, collaboration and delivery
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- Strong product sense and the ability to turn messy customer problems into simple, valuable product experiences
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- Strong customer discovery skills and the ability to separate real customer problems from shiny AI ideas
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- Valuable judgement around trust, risk, permissions, explainability, auditability 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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- Pragmatic, curious and ownership-oriented, with the ability to operate in ambiguity and drive work forward
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Nice to Have nn
- Experience building AI-powered products, AI agents, copilots, agentic workflows or automation-heavy products
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- Experience designing or managing products that use subagents, AI skills, tool calling, retrieval systems or orchestration layers
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- Experience working with AI evaluation frameworks, AI observability tooling or human review workflows
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- Experience using AI tools such as ChatGPT, Claude, Cursor, Copilot or similar to improve product workflows, technical collaboration, research, documentation, testing or iteration
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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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What We Offer nn
- 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 core strategic product area
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- Opportunity to shape how AI and agentic workflows are built into a category-defining SaaS platform
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- Personal learning and development budget
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- Flexible leave policy
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- Expense policy and salary sacrifice options
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- CBD start-up hub with snacks, drinks, premium coffee and team socials
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- Company-wide social events and annual off-sites
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- Transparent, flat culture where questions and feedback are welcomed
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📌 Senior Technical Product Manager, AI Products Product · Sydney · Full time · Hybrid
🏢 Checkbox
📍 Sydney