Legal Engineer

The Position

At Checkbox, we set a high bar for customer experience. It’s what we are known for, what we celebrate internally, and a core driver of our success. Our customers choose us not only for category-defining technology, but for a team that delivers measurable outcomes and sustained impact across their legal function. That standard shapes how we hire, how we operate, and how we partner.

As a Legal Engineer, you will be a legal domain expert embedded within our Customer Success team. This role combines deep legal expertise with technical solution design to help enterprise legal teams successfully adopt and scale Checkbox. You will translate how legal teams actually work - their judgment, risk tolerance, workflows and constraints - into scalable product behavior, helping customers get AI working quickly and effectively.

You will partner closely with Customer Success Managers, Product and Engineering teams to remove adoption barriers, design practical solutions and ensure Checkbox delivers impact in real-world legal environments. If you are a lawyer who enjoys fixing problems, building systems, shaping tools, and turning messy legal reality into something scalable, this role is for you.

In This Position, You Will

Serve as the technical and legal architect in strategic customer engagements, especially where nuance and ambiguity require structured solutions

Guide customers in expanding from initial use cases to broader functional or departmental adoption across enterprise legal teams

Identify workflow gaps or friction points and implement structured improvements that increase usage and reliability

Help reduce time-to-value for legal teams adopting our platform

Translate recurring customer requirements into reusable templates and standardized solution patterns

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

Help ensure our AI features are interpretable, defensible, and trusted by legal users

Model legal workflows such as intake, triage, approvals, risk assessment and outcomes

Define legal defaults, guardrails, and exception paths

Help design legal abstractions that work across customers and jurisdictions

About You

Experience Legal Operations professional or Paralegal

3+ years working in-house, ideally across legal teams of varying sizes

Passionate about technology, systems and operational efficiency

Background in legal operations, legal tech or process improvement

Experience implementing legal tech or workflows

First-hand use of AI tools as part of daily legal workflow

Interest & exposure to AI-enabled products & automation

Ability to think in term of systems, workflows, abstractions & patterns

Comfortable working in ambiguous, fast-paced environments