Customer Solutions Architect

Checkbox is a Sequoia-backed company building AI-powered Service Management for in-house legal teams. Sales has Salesforce, IT has ServiceNow, and Support has Zendesk. Legal is the last major function without its own platform, and that’s what we’re building. Today, legal departments at companies like SAP, Hitachi and Pepsi use Checkbox to manage how legal work comes in, gets routed, and gets resolved.

We’re a team of 100+ across the United States, Australia and Asia, and our culture is one of our superpowers. Read about what makes a “Checkmate” here: https://www.checkbox.ai/core-values.

The Position

Customer experience is what Checkbox is known for. As a Customer Solutions Architect, you’ll be the technical lead for our enterprise customers. You’ll design, build and configure the workflows, integrations and custom functions that get large legal teams live quickly and keep them scaling.

You don’t need a legal background, because our Legal Engineers bring the legal domain depth. What you bring is the technical architecture, the confidence in front of enterprise customers, and the instinct to build things yourself.

In This Position, You Will

• Own technical solution architecture and design for enterprise customers

• Build and configure complex Checkbox solutions and custom functions

• Design and lead integrations across APIs, SSO, SCIM, and enterprise systems

• Serve as the technical lead across implementations, workshops, demos, and proofs of concept

• Turn recurring customer requirements into reusable technical patterns, templates, and best practices that scale delivery

• Deliver Checkbox configuration as part of professional services engagements

• Reduce time-to-value and guide customers from their first use case to broader departmental adoption

• Bring field insights and deployment complexity back to Product and Engineering to inform roadmap priorities

About You

• 4+ years in a customer-facing technical role, such as Solutions Architect, Solutions or Sales Engineer, Implementation Consultant, or Technical Account Manager, at a B2B SaaS company

• A track record of delivering for large enterprise customers

• Hands-on experience with APIs, webhooks, and identity integrations (SSO/SAML, SCIM)

• A builder: you configure, prototype, and ship solutions yourself rather than handing off specs. Experience with low-code or no-code workflow platforms or scripting is a plus

• Confident leading workshops and demos with senior stakeholders

• Able to think in terms of systems, workflows, abstractions, and patterns

• Comfortable working in ambiguous, fast-paced environments

• Exposure to legal or legal tech is a plus, not a requirement

Benefits

• 20 days PTO per year, with rollover of unused leave (paid out upon leaving the company)

• 11 days paid Federal holidays per year

• Paid parental leave (primary and secondary)

• Health insurance, including dental and vision coverage

• 401K retirement savings match

• Fully paid annual trips to company offsites (past destinations include Australia, Bali, South Korea)