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About the Role

Partner with enterprise legal teams to ensure they realize meaningful business outcomes with Checkbox. Guide customers from initial adoption through long-term growth, helping them embed Checkbox into their legal workflows and achieve measurable operational impact. Own the health, retention, and expansion of a portfolio of enterprise customers.

Responsibilities

• Take ownership of enterprise customers as they transition from onboarding toward go-live, ensuring a smooth handoff and continuity in the customer journey.
• Ensure customers successfully embed Checkbox into their legal workflows after go-live, helping legal teams transition from initial deployment to meaningful operational impact across their organisation.
• Build trusted relationships with stakeholders across legal, operations, and business teams, positioning Checkbox as a strategic platform within their legal operations ecosystem.
• Identify and drive opportunities to expand Checkbox usage by introducing new workflows, departments, and use cases that increase the platform’s value across the organisation.
• Own the retention and renewal of your portfolio of enterprise customers by ensuring continued alignment between customer goals and the outcomes delivered through Checkbox.
• Lead strategic conversations with customers through regular check-ins, business reviews, roadmap discussions, and workflow optimisation sessions.
• Capture structured feedback and usage insights from customers and partner with Product and Engineering to inform roadmap priorities and improve the platform.
• Drive advocacy initiatives including customer success stories, reviews, and testimonials that showcase the impact of Checkbox across customer organisations.
• Leverage data and customer insights to monitor account health, identify risks and growth opportunities, and guide proactive engagement strategies.
• Lead the resolution of complex customer challenges by coordinating with internal teams and ensuring timely, effective outcomes for customers.

Requirements

• 5+ years of experience in customer success or account management, with a proven track record of managing large, complex enterprise accounts and delivering results.
• Experience working in legal technology or supporting legal and legal operations teams is strongly preferred.
• Understand the workflows, stakeholders, and operational challenges faced by in-house legal departments.
• Ability to think strategically and see the big picture, while also being detail-oriented and hands-on in execution.
• Connect customer goals with product capabilities to guide customers toward meaningful outcomes.
• Strong understanding of SaaS products and experience working closely with technical teams to deliver tailored solutions for customers.
• Experience with legal tech, workflow automation, or no-code platforms is a plus.
• Relentless focus on customer success, with the ability to build and sustain trusted, long-term relationships with stakeholders across customer organisations.
• Strong commercial mindset to customer engagement.
• Comfortable identifying expansion opportunities, leading upsell conversations, and managing renewals to drive long-term account growth.
• Excellent interpersonal and communication skills, with the ability to confidently lead complex discussions, workshops, and executive-level conversations with both technical and non-technical stakeholders.
• Comfortable working in a fast-paced, high-growth environment, managing multiple priorities and navigating ambiguity with confidence.
• Results-driven mindset with a strong track record of improving customer outcomes and driving key success metrics such as adoption, retention, expansion, NPS, and overall account health.

Skills

• Legal tech
• Workflow automation
• No-code platforms
• SaaS products
• Customer success
• Account management
• Relationship building
• Commercial mindset
• Strategic thinking
• Data analysis

Location

• Sydney

Work Type

• Full-time
• Hybrid

Experience Level

• Senior

Benefits

• Competitive salary and equity
• Hybrid working from our Sydney office
• Personal learning and development budget
• Flexible leave policy
• Paid parental leave, including primary and secondary carer leave
• Expense policy and salary sacrifice options
• CBD start-up hub with snacks, drinks, premium coffee and team socials
• Fully paid annual trips to company offsites, with past destinations including Australia, Bali and South Korea
• Transparent and open culture where questions and feedback are welcomed

About 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.