Product Manager, AI Experiences

Full-time | Hybrid, Sydney

The Company

Checkbox is a Series A, Sequoia-backed technology company on a mission to enable meaningful work for all.

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.

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.

The Role

We’re looking for a Product Manager to shape how users interact with AI across Checkbox. 

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.

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.

What You’ll Do

• Own AI-powered product experiences across legal intake, triage, matter management and workflow orchestration.

• Work with customers and internal teams to understand legal workflows, pain points and high-value AI opportunities.

• Translate ambiguous AI ideas into clear product problems, user journeys, requirements and success metrics.

• Partner with Design to create AI experiences that feel intuitive, transparent and trustworthy.

• Partner with Engineering to define how AI capabilities should behave across context, workflows, actions, review and escalation.

• Prioritise opportunities based on customer value, technical feasibility, strategic importance and speed to market.

• Work with Data and AI Evaluation teams to understand how AI experiences perform in production and where they need to improve.

• Support GTM teams with clear positioning, enablement and customer understanding of new AI capabilities.

What We’re Looking For

• Product management experience in B2B SaaS, enterprise software, workflow automation, AI products or complex productivity tools.

• Strong product sense and the ability to turn messy customer problems into simple, valuable product experiences.

• A practical understanding of modern AI product patterns such as assistants, copilots, RAG, agents, context, tool use and human-in-the-loop workflows.

• Experience working closely with engineers and designers from discovery through delivery.

• Strong customer discovery skills and the ability to separate real problems from shiny AI ideas.

• Good judgement around trust, risk, permissions, explainability and user control in AI-powered workflows.

• Clear communication skills and the ability to align technical and non-technical stakeholders.

• A pragmatic, curious and ownership-oriented mindset.

Nice to Have

• Experience building AI-powered products, copilots, agentic workflows or automation tools.

• 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.

• Experience working with data scientists, AI evaluation teams or AI observability tooling.

Why Join Us

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.

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 modern organisations.

Benefits

• Competitive salary and equity.

• Hybrid working from our Sydney office.

• High ownership and direct impact on a strategic product area.

• A collaborative, ambitious team building category-defining software for legal teams.