Director - Head of Legal Operations & Innovation

THE LEGAL TEAM

Who We Are

HubSpot’s Legal team is a proactive, business-enabling partner, not a back-office function. We help our teams move fast, smart, and responsibly. As HubSpot transforms into an AI-native company, Legal isn’t just keeping pace. It’s leading the way. We’re building an AI-first legal team that scales judgment, not just headcount, and delivers clarity and speed at every level of the business.

How We Work

At HubSpot, Legal is a growth engine. We value clarity over complexity, ownership over bureaucracy, and systems thinking over one-off heroics. If you believe the best legal teams aren’t just staffed well, they’re engineered well. Let’s talk.

THE ROLE

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

1. 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: which opportunities to prioritize, in what order, and why. Stay current with the legal tech and AI market to make informed build vs. buy decisions, knowing when commercial tools, custom builds, or AI-augmented solutions best serve Legal’s needs. Own the roadmap. Drive it.
• Know what to build and how. Assess how legal work flows across intake, contracting, research, advice, and reporting. Apply the right approach: workflow automation for deterministic, rules-based processes; an AI agent when the work requires multi-step reasoning and judgment; a redesign of the process itself when the real problem is how the work flows, not how fast it runs.
• Build for production. Design and deploy AI-powered workflows across priority use cases with error handling, audit trails, privilege-awareness, and human-in-the-loop checkpoints built in from the start. Partner with IT to build and integrate what you design.

1. Manage Governance and Risk

• Risk-tier every build. Classify all automation by risk tier before work begins. No build goes to production without a named process owner, documented data flows, access controls confirmed, and privilege impact assessed.
• Govern what you deploy. Maintain audit logging for all systems touching privileged work product, attorney communications, or regulated data. Halt or redesign builds that introduce unacceptable privilege, regulatory, or data privacy risk, own that decision, and secure organizational acceptance before proceeding.
• Own the data layer. Design data flows so legal data, contracts, matters, requests, and workflow events, is structured, queryable, governed for privilege, and ready for analytics and AI use cases. Own data quality, lineage, and auditability across systems.

1. Upskill the Team

• Build AI fluency across the team. Train attorneys and legal staff on AI-assisted tools and workflows in production. Build confidence and capability so Legal compounds over time, human judgment and AI working together, not in parallel.
• Build for scale and handoff. Produce documentation, workflow templates, and runbooks that team members can use and maintain without ongoing technical support. Keep Legal’s SOPs, playbooks, and precedent libraries current, findable, and where possible AI-searchable.
• Make the impact visible. Track and report quarterly on automation impact: turnaround time reduced, matters per attorney increased, attorney capacity unlocked for higher-judgment work. Set baselines, define targets, and hold the program accountable to both.

WHAT SUCCESS LOOKS LIKE

• Legal workflows are faster, more scalable, and more resilient through a mix of automation, agents, and human review.
• 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. No shelfware. No abandoned launches.

WHAT YOU’LL BRING

• 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, not just experimentation.
• 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.

WHY HUBSPOT

HubSpot’s mission is to help millions of organizations grow better. Our AI-powered customer platform, anchored in our Smart CRM, powers marketing, sales, service, CMS, operations, and commerce for over 260,000 customers in 135+ countries.

We’ve built a world-class legal team. Now we’re building the operating model to match, and this role is where that work gets done. Not planned. Not pitched. Done. If you want to be the person who engineers what an AI-first legal function looks like in practice and can point to the workflows, systems, and outcomes you built, this is the right seat.