Senior Customer Solutions Specialist

The Company

Checkbox is a Sequoia-backed legal technology company on a mission to enable meaningful work for all. We build AI-powered software that helps in-house legal teams manage, automate, and scale their operations, from intake and triage to workflow automation, matter management, and reporting.

Our belief is simple: meaningful work happens when teams are empowered to focus on impact, not admin. With Checkbox, legal teams streamline how work is captured, routed, managed, and resolved, freeing lawyers to do more of what matters most.

Today, Checkbox is trusted by leading global organizations including SAP, BMW, Allianz, Coca-Cola, and Hitachi. Our customers use Checkbox to power everything from contract review and compliance workflows to matter tracking and reporting, all within a single, AI-powered platform.

While most technology in the legal space has focused narrowly on contract lifecycle management (CLM), Checkbox takes a broader view offering an intelligent modular platform that scales alongside business growth. Our platform acts as the central front door and operating system for all legal work, enabling legal teams to start small, expand over time, and continuously unlock new efficiencies. We believe this flexible, scalable approach will become indispensable for managing all legal work – and Checkbox will lead that category.

We’re a tight-knit global team of 50+ people across the United States, Australia, and Asia, including Forbes 30 Under 30 founders and a group of ambitious, high-performing individuals driven by impact, ownership, and excellence. Our culture is one of our superpowers. It’s what people talk about when they join us, work with us, and even after they leave.

Read about what makes us “Checkmates” here: https://www.checkbox.ai/core-values

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Role Overview

The Senior Customer Solutions Specialist is a key member of the Customer team, responsible for guiding clients through the implementation and adoption of Checkbox solutions. This role combines solution design, customer success, and technical consulting to ensure clients extract maximum value from our platform.

You will lead solution delivery projects end-to-end, mentor, and coach solution consultants, and act as the strategic advisor to clients on Checkbox solutions.
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Key Responsibilities

Customer Success & Engagement

+ Own end-to-end client solution delivery for Enterprise and Strategic accounts.

+ Act as a strategic advisor - guiding clients on automation opportunities and best practices.

+ Build strong, trusted relationships with client stakeholders (Legal, Ops, Business teams).

+ Drive product adoption and measurable business outcomes for clients.
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Solution Design & Delivery

+ Lead the discovery, scoping, and implementation of Workflow, Intake, and Matter Management solutions using Checkbox.

+ Create JavaScript custom functions and integrations as required.

+ Translate client requirements into scalable and user-friendly solutions.

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Leadership & Enablement

+ Coach and mentor Solution Consultants, supporting their technical and client-facing development.

+ Establish and maintain best practices, templates, and playbooks for consistent solution delivery.

+ Collaborate cross-functionally with Product and Customer success to influence product roadmap and customer success processes.

+ Develop resources (knowledge base content, implementation guides, training materials) to scale client enablement.

+ Identify opportunities to improve delivery efficiency and expand reusable assets.

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‍About you

Skills & Experience

+ Experience in computer software, software engineering or related field.

+ Strong analytical and problem-solving mindset, with the ability to translate business requirements into digital solutions.

+ Excellent client engagement skills, with the ability to consult and influence at senior stakeholder levels.

+ Experience mentoring delivery teams or junior consultants is preferred.

+ Prior work experience in a Seed, Series A, or Series B startup.

Personal Attributes

+ Strategic thinker with strong ownership and accountability.

+ Exceptional communication skills - both written and verbal.

+ Adaptable, resourceful, and comfortable in a fast-paced startup environment.

+ Able to work effectively with team members located in Australia and the United States.

+ Passionate about technology, innovation, and helping customers succeed.

‍Why Join Us?

+ Opportunity to shape how global organizations transform their operations through no-code automation.

+ Be part of a fast-growing, innovative legaltech/enterprise SaaS company.

+ Work alongside a driven, collaborative, and supportive team.

+ Hybrid flexible working model with Sydney HQ.

+ Competitive salary, equity options, and professional development opportunities.