Head of Legal

Retool•Remote, US

About The Position

Retool is hiring a senior legal leader to build and lead a legal function that can scale with the company. The Head of Legal owns commercial and vendor contracting, privacy and compliance, and corporate matters including governance, employment, intellectual property, and financing. The role combines hands-on legal work—negotiating key deals and creating playbooks and policies—with executive-level advice on risk and business opportunities in an evolving AI-focused environment. The position reports to the CFO and works closely with Sales, Finance, Trust, Product, and People. The Head of Legal leads the existing legal team, sets priorities, serves as the first point of contact for legal questions across the company, and engages outside counsel when appropriate. The role is intended to make legal a business enabler and to guide the company through changes AI brings to its products and legal practice.

Requirements

J.D. and active bar membership in at least one U.S. jurisdiction.
10+ years of experience at a law firm and/or in-house, with deep exposure to B2B SaaS commercial contracting across customer and vendor relationships.
Prior experience leading or managing attorneys or a legal function, or a clear track record of readiness to do so.
Strong working knowledge of privacy and data protection frameworks, including GDPR and CCPA, and their application to enterprise SaaS and AI products.
Familiarity with AI-specific legal issues, including model and data licensing, IP ownership, and emerging regulation.
Sound judgment on risk, including the ability to distinguish matters requiring escalation from those that can be resolved directly and explain tradeoffs to executives in plain language.
Comfort with high-volume, fast-moving commercial work and the ability to prioritize and execute independently.
Excellent written and verbal communication, including the ability to translate legal concepts for non-lawyer audiences.
Genuine curiosity about AI tools and legal technology, and willingness to use them to work more efficiently.
Impeccable ethical standards.

Nice To Haves

Experience with contract management systems such as Ironclad or similar.
Corporate governance, financing, or employment law experience.

Responsibilities

Lead and develop the legal team, set priorities, coach attorneys and legal operations staff, and determine when to hire, automate, or use outside counsel.
Own the commercial contracting program and handle escalations involving complex or non-standard MSAs, DPAs, order forms, and partnership agreements; partner with Sales leadership on strategic and enterprise deals.
Oversee the vendor contract program, including risk positions and approval thresholds.
Lead privacy and data protection legal work involving GDPR, CCPA, and emerging state and international regimes across contracts, product features, and customer security reviews.
Advise on AI legal and regulatory matters, including customer-facing AI terms, responsible use, intellectual property and data rights, and evolving regulation, in partnership with Product, Engineering, and Trust.
Build and maintain legal infrastructure, including contract intake and CLM workflows, templates, negotiation playbooks, policies, and process documentation; use AI where it improves speed and consistency.
Partner with Finance, Accounting, Trust, People, and other teams to provide practical guidance on operational matters, including employment, intellectual property, and compliance.
Manage outside counsel relationships and the legal budget.
Support corporate matters such as governance, equity administration, and financing or corporate development projects with the CEO and Finance.
Report legal risk, workload, and team performance to company leadership, and escalate material issues early.