Legal Engineer

Checkbox AI•New York, NY

About The Position

The Legal Engineer is a legal domain expert embedded within Checkbox’s Customer Success team. The role combines legal expertise with technical solution design to help enterprise legal teams adopt and scale Checkbox. The Legal Engineer translates how legal teams work—including their judgment, risk tolerance, workflows, and constraints—into scalable product behavior, helping customers put AI to work quickly and effectively. Working closely with Customer Success Managers and Product and Engineering teams, the Legal Engineer removes adoption barriers, designs practical solutions, and helps ensure Checkbox delivers impact in real-world legal environments. The role also helps make AI features interpretable, defensible, and trusted by legal users.

Requirements

Experience as a Legal Operations professional or Paralegal.
At least 3 years working in-house, ideally across legal teams of varying sizes.
Passion for technology, systems, and operational efficiency.
Background in legal operations, legal tech, or process improvement.
Experience implementing legal technology or workflows.
First-hand use of AI tools as part of a daily legal workflow.
Ability to think in terms of systems, workflows, abstractions, and patterns.
Comfort working in ambiguous, fast-paced environments.

Nice To Haves

Interest in and exposure to AI-enabled products and automation.

Responsibilities

Serve as the technical and legal architect in strategic customer engagements, particularly 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 the platform.
Translate recurring customer requirements into reusable templates and standardized solution patterns.
Bring field insights and deployment complexity to Product and Engineering to inform roadmap priorities.
Help ensure 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.

Benefits

20 days of PTO per year, with rollover of unused leave; unused leave is paid out upon leaving the company.
11 paid Federal holidays per year.
Paid parental leave for primary and secondary parents.
Health insurance, including dental and vision coverage.
401(k) retirement savings match.
Fully paid annual company offsite trips.

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