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)
Skills Required
- 4+ years of experience in a customer-facing technical role, such as Solutions Architect, Solutions Engineer, Sales Engineer, Implementation Consultant, or Technical Account Manager, at a B2B SaaS company
- Track record of delivering solutions for large enterprise customers
- Hands-on experience with APIs, webhooks, and identity integrations, including SSO/SAML and SCIM
- Ability to configure, prototype, and ship solutions independently
- Experience leading workshops and demos with senior stakeholders
- Ability to think in terms of systems, workflows, abstractions, and reusable patterns
- Comfort working in ambiguous, fast-paced environments
- Experience with low-code or no-code workflow platforms or scripting
- Exposure to legal or legal technology
What We Do
Checkbox is the legal intake and workflow automation platform used to capture requests from the business, gain visibility and control over all matters, and automate manual work.
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