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 n
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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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Good 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 n
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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 n
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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 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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Adaptable 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 (New South Wales)
🏢 Checkbox.ai
📍 New South Wales