Senior Technical Product Manager, AI Products

Full-time | Hybrid | Sydney

The Company

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.

The Role

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.

What You’ll Own

• 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

About You

• 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

Nice to Have

• 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

What We Offer

• 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