Counsel - AI (Innovation & Trust), Commercial & Procurement

KAYAK, 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 Counseling

• Draft, review, and negotiate commercial agreements, with a focus on enterprise and partner deals (MSAs, SOWs, pilot and evaluation agreements, privacy addenda) and AI/SaaS vendor agreements

• Develop and maintain standard AI contract provisions and negotiation playbooks so terms stay consistent across deals

• Advise Product and Engineering on AI-enabled features, consumer and B2B terms of use, disclosures, and product compliance

• Give sound, timely, risk-calibrated advice to business partners across the company

What Success Looks Like
In Your First 90 Days

• Get to know KAYAK’s artificial intelligence governance process, the KAYAK for Business (K4B) contracting pipeline, and the legal agents and self-service tools already in place.

• Take ownership of the AI Risk Assessment (AIRA) intake queue and the AI Governance Committee cadence to ensure reliable, timely responses for stakeholders.

• Relaunch the Legal & Compliance Team’s Self-Help Portal education roadshow and begin introducing its resources to stakeholders across the business.

• Deliver at least one new or meaningfully improved legal agent or automation, with clear measures to evaluate its impact.

In Your First Year

• Build a documented framework for developing legal agents—including standards, testing, ownership, and a roadmap—that enables other members of the Legal team to contribute.

• Improve turnaround time and reduce lawyer time spent on high-volume, low-risk requests, with measurable results.

• Become a trusted, embedded legal partner to KAYAK for Business and Product teams on AI-related matters.

Please Apply If You Have

• A J.D. from an accredited law school and active bar admission in good standing in at least one U.S. jurisdiction; a strong academic background is valued, and we welcome candidates from a wide range of institutions and professional paths

• At least 5 years of experience in-house and/or at a law firm, including drafting and negotiating complex commercial, technology, SaaS, or data agreements — equivalent experience, training, or transferable skills are considered

• Hands-on experience building with AI: you have designed and shipped working agents, assistants, or automated workflows (not just used AI tools) — this role involves building AI-powered legal systems, and demonstrated comfort with scripting, low-code tools, or automation (e.g., Python, JavaScript, APIs, Zapier/Make, Jira automation) is important

• Working knowledge of AI and data protection law and governance frameworks (e.g., EU AI Act, GDPR, U.S. state privacy and AI laws, NIST AI RMF)

• Systems thinking: you naturally turn recurring questions into playbooks, templates, decision trees, and self-service tools

• Comfort with technical detail: you can talk to engineers about data flows, model behavior, integrations, APIs, and access controls, and pick up new tools quickly

• Clear, plain-English writing and the ability to explain complex legal and technical risks to non-lawyers

• Good judgment, high integrity, and the ability to make practical calls when things are ambiguous

• The ability to balance many matters at once, reprioritize quickly, and work proactively and independently

Helpful but not required:

• IAPP certification (AIGP, CIPP/US, CIPP/E, or CIPT)

• A background in legal operations, product, or engineering

• Experience with legal tech such as CLM, intake and ticketing, contract analytics, and enterprise AI platforms

• Experience with B2B travel, marketplace, or platform businesses, or with a multi-brand corporate group

• Multi-jurisdictional experience

Compensation

There are a variety of factors that go into determining a salary range, including but not limited to external market benchmark data, geographic location, and years of experience sought/required. The range for this Massachusetts based role is $125,000 - $150,000 not inclusive of annual bonus and recurring RSU grants.

We offer a competitive base salary and benefits including: health benefits; flexible spending account; retirement benefits; life insurance; paid time off (including PTO, paid sick leave, medical leave, bereavement leave, floating holidays and paid holidays); and parental leave benefits.

Inclusion
At KAYAK, we want everyone to have the space to grow, share ideas and do great work. That's why we're focused on hiring the best talent from all walks of life and experiences, supporting them well and making sure no one feels like they have to fit a mold to belong here.

Need any adjustments for the interview, application or on the job? No problem – just give us a heads-up. We've got you.

#AC-LI