Legal Engineer — AI-Driven Legal Ops Architect

Checkbox AI; New York (NY); On-site; USD 120,000 - 180,000; Full time

Benefits offered by this job

20 days PTO per year, with rollover of

11 days paid Federal holidays per year

Paid parental leave (primary and…

Health insurance, including dental and

401K retirement savings match

Fully paid annual trips to company off

Job summary

Checkbox AI is seeking a Legal Engineer to be embedded within the Customer Success team. You will blend legal expertise with product-minded design to help enterprise legal teams adopt and scale Checkbox AI-powered service management.

You will translate how legal teams work—their judgment, workflows, and risk tolerance—into scalable product behavior that delivers quick, real-world impact. You will partner with Customer Success Managers, Product and Engineering to remove adoption barriers, design

Qualifications

• 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 terms of systems, workflows, abstractions & patterns.
• Comfortable working in ambiguous, fast-paced environments.

Responsibilities

• 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

Skills

Legal Operations

Paralegal background

In-house experience

AI tools exposure

Job description

Checkbox AI is seeking a Legal Engineer to be embedded within the Customer Success team. You will blend legal expertise with product-minded design to help enterprise legal teams adopt and scale Checkbox AI-powered service management.

You will translate how legal teams work—their judgment, workflows, and risk tolerance—into scalable product behavior that delivers quick, real-world impact. You will partner with Customer Success Managers, Product and Engineering to remove adoption barriers, design