Director - Head of Legal Operations & Innovation

Overview

A leading organization is seeking a Head of Legal Operations & Innovation to lead the design and implementation of AI-powered solutions within its Legal team. This role focuses on combining human judgment with AI capabilities to enhance the speed, scale, and efficiency of legal workflows. The position involves full ownership of strategy, solution design, deployment, governance, and capability transfer in collaboration with the Chief Legal Officer, Legal leadership, and IT.

Responsibilities

• Define and own the AI transformation strategy and multi-horizon roadmap for the Legal team, prioritizing opportunities and making build vs. buy decisions based on current legal tech and AI market trends.
• Assess legal workflows across intake, contracting, research, advice, and reporting to determine the appropriate automation or AI approach.
• Design and deploy AI-powered workflows with built-in error handling, audit trails, privilege-awareness, and human-in-the-loop checkpoints.
• Partner with IT to build and integrate designed solutions.
• Classify all automation by risk tier before production deployment, ensuring named process ownership, documented data flows, access controls, and privilege impact assessments.
• Maintain audit logging for systems handling privileged work product, attorney communications, or regulated data.
• Halt or redesign builds that introduce unacceptable privilege, regulatory, or data privacy risks, securing organizational acceptance before proceeding.
• Design and own the data layer to ensure legal data, contracts, matters, requests, and workflow events are structured, queryable, governed for privilege, and ready for analytics and AI use cases.
• Build AI fluency across the Legal team by training attorneys and staff on AI-assisted tools and workflows.
• Produce documentation, workflow templates, and runbooks for scalable maintenance without ongoing technical support.
• Keep standard operating procedures, playbooks, and precedent libraries current and AI-searchable where possible.
• Track and report quarterly on automation impact metrics such as turnaround time reduction, increased matters per attorney, and unlocked attorney capacity.

Requirements

• 8+ years in a technical, operations, or engineering-adjacent role with proven experience executing automation and AI solutions at scale.
• Hands-on experience designing and deploying AI-powered or automated workflows in production environments.
• Strong experience with API integration and middleware, including REST APIs, JSON, webhooks, authentication, error handling, and observability.
• Proficiency in scripting or automation languages such as Python or SQL for building integrations and backend services.
• Experience building with large language model (LLM) APIs, including tool-calling and multi-step agentic workflows.
• Expertise in designing agentic systems with human-in-the-loop review and safety constraints.
• Ability to translate ambiguous operational requirements into reliable, production-grade technical systems.
• Strong systems thinking regarding reliability, security, permissions, and data integrity.
• Solid understanding of data classification, personally identifiable information (PII) handling, and applicable privacy and data protection regulations.
• Experience implementing governance and risk frameworks for AI or automation systems, including risk tiering, human review gates, audit logging, and data classification.
• Excellent written and verbal communication skills, capable of explaining technical solutions to lawyers, senior leadership, and non-technical stakeholders.

Preferred Qualifications

• Experience working with legal teams or within a legal department, with knowledge of legal work product production, review processes, and attorney-client privilege as it applies to technology systems.
• Hands-on experience with legal technology platforms such as contract lifecycle management (CLM), matter management, spend management, or legal research tools.
• Background in legal operations including intake design, vendor management, knowledge management, or reporting.
• Experience using AI for document analysis, contract review, research summarization, or regulatory analysis.
• Prior experience establishing a legal technology, legal automation, or legal innovation function.

Compensation & Benefits

• Annual cash compensation range: $161,500 to $258,400 USD, including base salary, on-target commission (if applicable), and annual bonus targets.
• Eligibility for participation in an equity plan with restricted stock units (RSUs) for some roles.
• Some roles may be eligible for overtime pay.
• Individual compensation packages are tailored based on skills, experience, qualifications, and other job-related factors.
• Comprehensive benefits and perks designed to support employee growth and well-being.

Location & Additional Information

• The organization values flexibility and connection, offering remote and office-based work options.
• New hires in engineering roles are required to attend regional office onboarding in person.
• Candidates requiring accommodations during the hiring process or onboarding are encouraged to request assistance.
• Compliance with applicable employment laws, including those specific to Massachusetts, Germany, and India, is maintained.

Qualified candidates are encouraged to apply regardless of confidence level, as the organization values diverse talent and is committed to equitable hiring practices.