Legal Engineer

Checkbox is a Sequoia-backed software company building the AI Legal Front Door for in-house legal teams. General Counsels and Legal Operations use Checkbox to redefine how legal work enters, flows through, and gets resolved inside enterprise companies. Our customers today are the in-house legal departments from companies like SAP, Hitachi, and Pepsi.

Support teams had Zendesk. Sales had Salesforce. IT had ServiceNow. Each became the defining system of record and engagement for their function, enabling new levels of scale, visibility, and impact. But more than that, each system fundamentally redefined how the function operated. Each of these business functions had its moment of transformation. And legal is next.

Until now, legal has been the last major business function without its own purpose-built platform to orchestrate workflows, manage service delivery, and demonstrate value to the business. This is what we’re building at Checkbox – AI-powered Service Management for in-house legal teams.

As a company, we are a passionate and ambitious team of 70+ people across the United States, Australia, and Asia, made up of high performers and Co-Founders in the Forbes 30 Under 30 list. Our culture is one of our superpowers. It's what people talk about when they join us, work with us, and leave us.

Read about what makes all of us a "Checkmate" here: https://www.checkbox.ai/core-values.

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
  

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)