Full-time | Hybrid | Sydney
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.
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.
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.
We are looking for a Senior Technical Product Manager, AI Products to shape how AI is used across Checkbox’s product suite.
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.
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.
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.
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.
Own AI product strategy and execution across legal intake, triage, matter management and workflow orchestration
Identify high-value AI opportunities through customer discovery, internal expertise and product usage data
Translate ambiguous AI ideas into clear product problems, user journeys, requirements and success metrics
Define how AI capabilities should behave across context, reasoning, actions, review, escalation and handoff
Shape agentic workflows, including skills, subagents, tool use, task boundaries and human-in-the-loop moments
Partner with Design and Engineering to create AI experiences that are intuitive, transparent, technically feasible and production-ready
Work with Data and AI Evaluation teams to understand AI performance in production and improve quality over time
Define evaluation criteria for AI-powered workflows, including accuracy, usefulness, grounding, latency, cost, safety and user trust
Help shape how Product, Design and Engineering use AI throughout the product development lifecycle
Support GTM teams with clear positioning, enablement and customer understanding of new AI capabilities
Senior product management experience in B2B SaaS, enterprise software, workflow automation, AI products or complex productivity tools
Strong technical fluency and confidence working closely with Engineering, Data and AI Evaluation teams
Practical understanding of AI product patterns such as assistants, copilots, RAG, agents, context, tool use, skills and human-in-the-loop workflows
Comfortable reasoning about model strengths, model weaknesses, failure modes, evals, prompt behaviour, retrieval quality and AI product reliability
Experience working in an AI-native SDLC, using AI tools to amplify product discovery, specification writing, analysis, prototyping, collaboration and delivery
Strong product sense and the ability to turn messy customer problems into simple, valuable product experiences
Strong customer discovery skills and the ability to separate real customer problems from shiny AI ideas
Good judgement around trust, risk, permissions, explainability, auditability and user control in AI-powered workflows
Clear communication skills and the ability to align technical and non-technical stakeholders
Pragmatic, curious and ownership-oriented, with the ability to operate in ambiguity and drive work forward
Experience building AI-powered products, AI agents, copilots, agentic workflows or automation-heavy products
Experience designing or managing products that use subagents, AI skills, tool calling, retrieval systems or orchestration layers
Experience working with AI evaluation frameworks, AI observability tooling or human review workflows
Experience using AI tools such as ChatGPT, Claude, Cursor, Copilot or similar to improve product workflows, technical collaboration, research, documentation, testing or iteration
Experience in legal tech, enterprise SaaS, no-code/low-code, workflow platforms or document-heavy products
Experience with products involving approvals, permissions, auditability, compliance or high-trust decisions
Competitive salary and equity
Hybrid working from our Sydney office
High ownership and direct impact on a core strategic product area
Opportunity to shape how AI and agentic workflows are built into a category-defining SaaS platform
Personal learning and development budget
Flexible leave policy
Expense policy and salary sacrifice options
CBD start-up hub with snacks, drinks, premium coffee and team socials
Company-wide social events and annual off-sites
Transparent, flat culture where questions and feedback are welcomed
