[Hiring] Head of Legal @Retool

Role Description

We’re hiring a Head of Legal to be Retool’s senior legal leader and the architect of a function built to scale. You’ll own the full scope of legal: commercial and vendor contracting, privacy and compliance, and the corporate matters that underpin a fast-growing company, including governance, employment, IP, and financing.

This is a role for a builder who still enjoys handling the details. You’ll negotiate the deals that matter most, write the first version of the playbooks and policies, and make the judgment calls in an evolving AI-centric space. You’ll also advise executives with GC-level credibility, shape how Retool weighs risk against opportunity, and grow a team that carries the work forward as the company scales.

This role reports to the CFO and partners closely with Sales, Finance, Trust, Product, and People. You’ll lead our existing legal team, set its priorities, and be the first stop for legal questions across the company, escalating to outside counsel where it makes sense.

If you want to run a legal function that acts as a business enabler rather than a checkpoint, and you’re energized by how AI is changing both our product and the practice of law, this role is for you.

Responsibilities

• Lead and develop the legal team, setting priorities, coaching attorneys and legal operations staff, and deciding when to hire, automate, or use outside counsel.
• Own the commercial contracting program, serving as the escalation point for complex or non-standard MSAs, DPAs, order forms, and partnership agreements, and partnering with Sales leadership on strategic and enterprise deals.
• Oversee the vendor contract program, setting the risk positions and approval thresholds that let business owners move quickly.
• Lead our privacy and data protection legal work (GDPR, CCPA, and emerging state and international regimes) as it arises in contracts, product features, and customer security reviews.
• Advise on the legal and regulatory landscape for AI, including customer-facing AI terms, responsible use, IP and data rights, and evolving regulation, working with Product, Engineering, and Trust.
• Build and maintain our legal infrastructure: contract intake and CLM workflows, templates, negotiation playbooks, policies, and process documentation, using AI wherever it improves speed and consistency.
• Partner with Finance, Accounting, Trust, People, and other teams to give practical, business-oriented guidance on day-to-day operational matters, including employment, IP, and compliance questions.
• Manage outside counsel relationships and the legal budget, and support corporate matters such as governance, equity administration, and financing or corporate development projects with the CEO and Finance.
• Report on legal risk, workload, and team performance to company leadership, and escalate material issues early.

Qualifications

• 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 both customer and vendor relationships.
• Prior experience leading or managing attorneys or a legal function, or a clear track record of readiness to do so (for example, as a senior counsel or director of legal).
• Strong working knowledge of privacy and data protection frameworks, including GDPR and CCPA, and how they apply to enterprise SaaS and AI products.
• Familiarity with legal issues specific to AI, such as model and data licensing, IP ownership, and emerging regulation.
• Sound judgment on risk: you can tell what needs escalating from what you can resolve, and you can 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 translating legal concepts for non-lawyer audiences.
• Genuine curiosity about AI tools and legal tech, and a willingness to use them to work more efficiently.
• Experience with contract management systems such as Ironclad or similar is a plus.
• Corporate governance, financing, or employment law experience is a plus.
• Impeccable ethical standards.