Lead - Conversational Interfaces

At Booking.com, data drives our decisions. Technology is at our core. And innovation is everywhere. But our company is more than datasets, lines of code or A/B tests. We’re the thrill of the first night in a new place. The excitement of the next morning. The friends you encounter. The journeys you take. The sights you see. And the memories you make. Through our products, partners and people, we make it easier for everyone to experience the world!

Role Overview

The Lead GenAI Conversational Interfaces drives the continuous improvement and optimization of a defined scope within the Digital Partner Ecosystem's conversational AI product portfolio (currently covering search experiences, agents as well as the underlying RAG infrastructure).

This role owns the performance, quality, and evolution of partner-facing conversational interfaces through content and related infrastructure enhancements - including knowledge architecture optimization, skills and evaluation framework management, and information retrieval systems.

Grounded in partner feedback and conversation data analysis, they deliver measurable improvements in partner self-service adoption, answer quality, and support efficiency while maintaining compliance with content governance and safety standards.

Operating within a collaborative framework, this role partners closely with fellow leads across distinct areas of the GenAI portfolio, Partner Support, Partner Hub backend and infrastructure, UX, as well as engineering, machine learning, data science, content, and legal/compliance teams. Clear scope definition and cross-functional alignment ensure efficient collaboration and avoid duplication across the GenAI product portfolio.

Key Job Responsibilities and Duties

Ownership: Scope

Drive the impact of partner-facing conversational AI on the Hub (Smart Search, Support Agent) through content and related infrastructure enhancements — including knowledge architecture optimization, skills and evaluation framework management, and information retrieval improvements. Focus on channel performance, partner experience quality, and content governance — aligned with department priorities and the innovations roadmap.

Ownership: Performance / Impact

Track and improve conversational AI KPIs — answer quality, task completion, self-service adoption, contact reduction, and partner satisfaction — identifying tactics/opportunities by diving into partner conversations, feedback, and operational data.

Use human-in-the-loop evaluation and in-product measurement to identify recurring issues, own the continuous feedback-to-improvement loop, and discover insights and opportunities for quality and operational health; not relying solely on automated judge scores.

Backlog Management

Own and prioritise the conversational AI channel backlog — including quality improvements, content guidelines work, measurement implementation, and partner experience enhancements — based on partner needs, business impact, technical feasibility, and compliance requirements. Align across the team on priorities across shared resources.

Partner Impact & Feedback Loop
Monitor live sessions and partner feedback for recurring pain points or quality gaps; resolve directly within own scope, and pass signals with innovation or roadmap implications to cross-functional leads and other key stakeholders.

Voice of the Partner

Represent the partner perspective decisions — incorporating partner feedback, session data, and content quality signals into solution design, and advocating for experiences with customer centricity.

Vendor / Budget Management

Coordinate and challenge internal and external contributors across product, engineering, data science, content, and vendor teams with clear requirements, priorities, and quality expectations.

Role Qualifications and Requirements

• Proven experience (4+ years) in Product Operations, Product Management, or Technical Program Management, with proven focus on driving continuous improvement and performance optimization of Conversational AI products in production.

• AI Operations & Continuous Improvement - Proven track record of running the day-to-day operations of a live AI/conversational product, driving continuous quality and content improvements based on real usage and partner feedback.

• Content & Prompt Execution - Hands-on experience writing and iterating on prompts, dialogue flows, and AI-served content at scale; understands how content and prompt changes affect AI output and can execute improvements directly, not just define standards for others.

• Business Acumen - Frames day-to-day work in terms of answer quality, self-service rates, and contact reduction; connects fixes and improvements to DPE commercial metrics and CS outcomes.

• Data-Driven Evaluation — Comfortable designing and interpreting AI quality evaluations, including human-in-the-loop frameworks, session analysis, and in-product measurement — not reliant solely on automated judge scores.

• Content & Conversational Governance — Understands how content quality and guidelines affect AI output; experience working with content teams to define and maintain standards for AI-served or AI-generated content at scale.

• Stakeholder Communication — Bridges technical and non-technical audiences; experienced in positioning AI work internally and translating complex technical concepts into clear business value propositions.

• Project Management — Methodical in breaking down complex cross-functional work and delivering against timelines independently.

• Technical Literacy — Understands knowledge architecture, retrieval systems, skills frameworks, evaluation methodologies, and GenAI infrastructure (RAG, LLM evaluation, model updates) well enough to challenge and prioritize technical decisions and scope boundaries without owning the underlying infrastructure implementation

Benefits & Perks - Global Impact, Personal Relevance:

Booking.com’s Total Rewards Philosophy is not only about compensation but also about benefits. We offer a competitive compensation and benefits package, as well unique-to-Booking.com benefits which include:

• Annual paid time off and generous paid leave scheme including: parent, grandparent, bereavement, and care leave

• Hybrid working including flexible working arrangements, and up to 20 days per year working from abroad (home country)

• Industry leading product discounts - up to 1400 per year - for yourself, including automatic Genius Level 3 status and Booking.com wallet credit

Inclusion at Booking.com:

Take it from our Chief People Officer, Paulo Pisano: “At Booking.com, the diversity of our people doesn’t just create a unique workplace, it also creates a better and more inclusive travel experience for everyone. Inclusion is at the heart of everything we do. It’s a place where you can make your mark and have a real impact in travel and tech.”

Read all about Inclusion and the Employee Resource Groups (ERGs) at Booking.com here

Career Development Opportunities

• Learn more about Your Career Journey here.

• Become a Mentee and benefit from a mentoring relationship with a more experienced person to help you identify and achieve your professional and personal development goals.

Booking.com is proud to be an equal opportunity workplace and is an affirmative action employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. We strive to move well beyond traditional equal opportunity and work to create an environment that allows everyone to thrive.