[Hiring] Director - Head of Legal Operations & Innovation @HubSpot

Role Description

We’re hiring a Head of Legal Operations & Innovation to serve as the primary architect and builder of AI-powered solutions within HubSpot’s Legal team. The goal: combine human judgment with AI capability so Legal can operate at a speed and scale it couldn’t reach alone. 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.

This role is for someone who builds production systems, not slide decks: someone who can assess a workflow in the morning, design the right AI approach by afternoon, and be measuring impact by end of month.

What You’ll Do

• Transform How We Work
  • Own the strategy and roadmap.
  • Define Legal’s AI transformation strategy and multi-horizon roadmap in partnership with the CLO and Legal leadership.
  • Stay current with the legal tech and AI market to make informed build vs. buy decisions.
  • Own the roadmap and drive it.
  • Assess how legal work flows across intake, contracting, research, advice, and reporting.
  • Apply the right approach: workflow automation, AI agents, or process redesign.
  • Design and deploy AI-powered workflows across priority use cases.
  • Partner with IT to build and integrate what you design.
• Manage Governance and Risk
  • Classify all automation by risk tier before work begins.
  • No build goes to production without a named process owner and documented data flows.
  • Maintain audit logging for all systems touching privileged work product.
  • Design data flows so legal data is structured, queryable, and ready for analytics.
  • Own data quality, lineage, and auditability across systems.
• Upskill the Team
  • Train attorneys and legal staff on AI-assisted tools and workflows.
  • Produce documentation, workflow templates, and runbooks for team members.
  • Track and report quarterly on automation impact.

What Success Looks Like

• Legal workflows are faster, more scalable, and more resilient.
• AI-powered systems are deployed responsibly, with clear guardrails and measurable impact.
• Legal data is structured, usable, governed for privilege, and trusted across systems.
• The legal tech stack has a clear, extensible architecture that supports rapid iteration.

Qualifications

• 8+ years in a technical, operations, or engineering-adjacent role.
• Hands-on experience designing and deploying AI-powered or automated workflows.
• Strong hands-on experience with API integration and middleware.
• Comfort with scripting or automation (e.g., Python or SQL).
• Hands-on experience building with LLM APIs.
• Experience designing agentic systems with human-in-the-loop review.
• Demonstrated ability to translate ambiguous operational requirements.
• Strong systems thinking around reliability, security, permissions, and data integrity.
• Solid understanding of data classification and applicable privacy obligations.
• Experience implementing governance and risk frameworks for AI or automation systems.
• Strong written and verbal communication skills.

Nice to Haves

• Experience working with lawyers or within a legal department.
• Hands-on experience with legal technology platforms.
• Background in legal operations including intake design or vendor management.
• Experience using AI for document analysis or contract review.
• Prior experience standing up a legal technology or legal innovation function.

Benefits

• Annual Cash Compensation Range: $161,500 — $258,400 USD.
• Equity plan eligibility for restricted stock units (RSUs).
• Flexible work arrangements to build strong connections with your team.