Counsel - AI (Innovation & Trust), Commercial & Procurement
KAYAKKAYAK, part of Booking Holdings (NASDAQ: BKNG), is a leading travel search engine. With billions of queries across our platforms, we help people find their perfect flight, stay, rental car, and vacation package. We're also transforming business travel with a new corporate travel solution, KAYAK for Business. As an employee of KAYAK, you will be part of a travel company that operates a portfolio of global metasearch brands including momondo, Cheapflights and HotelsCombined, among others. From start-up to industry leader, innovation is in our DNA, and every employee has an opportunity to make their mark. Our focus is on building the best travel search engine to make it easier for everyone to experience the world. KAYAK's Legal & Compliance team is looking for a builder-minded attorney who sits at the intersection of AI, law, and technology. This role is responsible for designing and operating the AI-powered legal systems that let a lean team scale — and for serving as KAYAK's primary counsel on AI governance, commercial agreements, and product compliance. The Counsel – AI & Commercial translates a rapidly evolving technology and regulatory landscape into practical, business-ready guidance that keeps KAYAK moving forward with confidence. This is not a traditional legal role. You will be our in-house expert developer of legal AI agents. That means you will look at a recurring legal process — such as contract triage, AI tool intake, NDA review, or regulatory horizon scanning — and turn it into a repeatable, AI-powered system the business can use on its own. Our goal is to move from handling requests one at a time to running scalable agent workflows that let a lean team do more. You will also serve as KAYAK's go-to counsel on AI governance. You will run the process that decides how AI tools are approved, contracted, and used across the company, and you will advise on AI-enabled product features and KAYAK for Business (K4B) enterprise deals. We prefer approachable team players — people who think about "how we can do this" and who bring a collaborative, low-ego approach to complex problems. You will spend approximately 3 days per week in our Concord office, with flexibility to work from the Cambridge office periodically. In This Role You Will Be Responsible For: Legal AI Enablement Design, build, test, and maintain legal AI agents and automations (for example: contract triage, NDA review, vendor light-review, meeting-minutes review, plain-English rewriting, and regulatory horizon scanning) Build a repeatable agent framework: shared standards for prompt design, playbook-grounded knowledge sources, evaluation and testing, versioning, human-in-the-loop review, and retirement of outdated tools Own and evolve the Legal Self-Help Portal as the single front door for legal intake, with self-service guidance, templates, and fast lanes for low-risk requests Map legal workflows end-to-end, find bottlenecks, and decide what should be automated, templated, self-served, or kept with a lawyer Train and coach the Legal & Compliance team on AI tools and prompting, and help colleagues build their own agents Represent Legal in company-wide AI adoption forums and partner with Engineering, IT, and Security on tooling AI Governance and Risk Lead KAYAK's AI risk assessment and approval process, from intake through cross-functional review and decision, for new AI tools, connectors, models, and agentic use cases Lead or co-lead the AI Governance Committee (Legal, Security, IT, Privacy, Engineering) and keep the company's AI tool registry accurate Maintain and update KAYAK's Generative AI Policy and related playbooks Advise on emerging AI regulation (EU AI Act, US state AI and privacy laws, and related frameworks) and turn it into clear, actionable guidance for the business Partner with Privacy, Security, and Procurement on AI vendor diligence, data-use and no-training commitments, and retention settings Commercial and Product Cou…