Director - Head of Legal Operations & Innovation

HubSpot

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About The Position

HubSpot’s Legal team is a proactive, business-enabling partner that helps teams move fast, smart, and responsibly. As HubSpot transforms into an AI-native company, Legal is leading the way by building an AI-first legal team that scales judgment, not just headcount, and delivers clarity and speed. This role is for someone who builds production systems, not slide decks, and can assess a workflow, design an AI approach, and measure impact efficiently. The Head of Legal Operations & Innovation will serve as the primary architect and builder of AI-powered solutions within HubSpot’s Legal team, combining human judgment with AI capability to operate at unprecedented speed and scale. This is a full-stack ownership role spanning strategy, opportunity identification, solution design, deployment, governance, and capability transfer, in partnership with the CLO, Legal leadership, and IT.

Requirements

• 8+ years in a technical, operations, or engineering-adjacent role with demonstrated execution of automation and AI solutions at scale.
• Hands-on experience designing and deploying AI-powered or automated workflows in a production environment used by others.
• Strong hands-on experience with API integration and middleware, including REST APIs, JSON, webhooks, auth, error handling, and observability.
• Comfort with scripting or automation, for example Python or SQL, for building integrations, automations, and backend services.
• Hands-on experience building with LLM APIs, including tool-calling and multi-step agentic workflows.
• Experience designing agentic systems with human-in-the-loop review and safety constraints.
• Demonstrated ability to translate ambiguous operational requirements into reliable, production-grade technical systems.
• Strong systems thinking around reliability, security, permissions, and data integrity.
• Solid understanding of data classification, PII handling, and applicable privacy and data protection obligations.
• Experience implementing governance and risk frameworks for AI or automation systems, including risk tiering, human review gates, audit logging, and data classification.
• Strong written and verbal communication skills, able to translate technical solutions for lawyers, senior leadership, and non-technical stakeholders.

Nice To Haves

• Experience working with lawyers or within a legal department, understanding how legal work product is produced and reviewed, and how attorney-client privilege applies to technology systems.
• Hands-on experience with legal technology platforms: CLM systems, 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 standing up a legal technology, legal automation, or legal innovation function.

Responsibilities

• Own the strategy and roadmap for Legal’s AI transformation, defining priorities and making build vs. buy decisions.
• Assess legal workflows (intake, contracting, research, advice, reporting) and apply appropriate solutions like workflow automation, AI agents, or process redesign.
• Design and deploy AI-powered workflows with error handling, audit trails, privilege-awareness, and human-in-the-loop checkpoints, partnering with IT for integration.
• Risk-tier all automation builds before work begins, ensuring process owners, data flows, access controls, and privilege impact are documented and confirmed.
• Govern deployed systems with audit logging for privileged work product, attorney communications, or regulated data, and halt or redesign builds that introduce unacceptable risk.
• Own the data layer, designing data flows for legal data, contracts, matters, and workflow events to be structured, queryable, governed for privilege, and ready for analytics and AI use cases.
• Train attorneys and legal staff on AI-assisted tools and workflows to build AI fluency and confidence.
• Produce documentation, workflow templates, and runbooks for team member maintenance and support.
• Keep Legal’s SOPs, playbooks, and precedent libraries current, findable, and AI-searchable.
• Track and report quarterly on automation impact, including turnaround time reduction, increased matters per attorney, and unlocked attorney capacity.

Benefits

• Cash compensation including base salary, on-target commission (for eligible roles), and annual bonus targets.
• Potential eligibility for HubSpot’s equity plan to receive restricted stock units (RSUs).
• Potential eligibility for overtime pay.
• Explore the benefits and perks HubSpot offers to help employees grow better.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed