Senior Product Manager, Conversational AI Experience

This role is eligible for our hybrid work model: 3 days in-office

Senior Product Manager, Conversational AI Experience
 

Our Product Design and Management teams work tirelessly to understand what our customers need and make it a reality. They’re the ones who make our deals come to life and our user experience simple and intuitive.

Why this job’s a big deal

We're hiring a product leader to shape how travelers interact with Penny, our AI travel assistant. This isn't a traditional mobile PM role – in conversational AI, the conversation is the interface.

You'll lead the end-to-end user experience across voice, text, and visual modalities. Reporting to our VP, Product, you'll partner with prompt engineers, designers, and AI developers to design interaction patterns, multimodal handoffs, and the micro-decisions that make Penny effective and trustworthy. You'll validate everything through rapid experimentation – testing conversation patterns to drive booking conversion, repeat usage, and customer satisfaction.

Think of yourself as the UX architect of Penny's conversational experience as we expand across platforms. We need someone who collaborates to bring personality and interaction patterns to life using AI, not just features and buttons.

What You’ll Do

• Define how users experience Penny's personality, tone, and interaction models across voice, text, and visual touchpoints

• Partner with other product leads to establish conversation design principles and requirements (when to use voice vs. visual, when to show vs. tell, proactive vs. reactive) and partner with the team to implement them

• Create patterns that scale across web, iOS, Android, voice assistants, and future modalities

• Translate user needs into conversation designs alongside AI experts

• Shape how voice, text, touch, and visual elements work together seamlessly

• Design transitions between modalities (voice search → visual selection → voice confirmation)

• Define interaction modes: conversational notifications, haptic feedback timing, natural gestures

• Ensure visual elements enhance dialogue without disrupting conversational flow

• Run systematic A/B tests on conversation UX: dialogue openings, AI proactivity, error recovery, context retention

• Test core hypotheses with users: optimal turn-taking, personality vs. efficiency balance, suggestion timing

• Track conversation metrics (turns-to-completion, abandonment, satisfaction) and their impact on booking conversion, repeat usage, and CSAT

• Partner with stakeholders to translate insights into improvements

• Lead execution of product roadmap for Penny across web, iOS, and Android

• Apply mobile capabilities (gestures, notifications, haptics, App Store dynamics) through a conversational lens

• Build consumer-grade experiences where AI conversation is the primary interface, not an add-on feature

• Ensure consistent, high-quality conversational experiences across all touchpoints

• Conduct research focused on conversation quality and interaction preferences

• Analyze transcripts and patterns to identify friction points and opportunities

• Advocate for UX decisions that increase trust, engagement, and task success

• Design for accessibility across modalities (captions, voice alternatives, varied interaction speeds)

What We’re Looking For

• 5–8 years in product management with 2–3 years focused on conversational AI, voice assistants, chatbots, or AI-native products

• Deep understanding of conversation design principles, dialogue state management, and multimodal interaction patterns

• Shipped consumer-facing AI products where conversation is the primary interface

• Strong intuition for how UX design decisions shape AI behavior and user perception

• Native mobile platform knowledge (iOS/Android): notifications, gestures, haptics, app store dynamics

• Experience launching mobile apps through an AI-native lens

• Experimentation mindset: Design tests, interpret results, iterate on interaction patterns

• Data-informed decision making: Balance quantitative metrics (completion, retention) with qualitative insights (conversation quality, sentiment)

• Cross-functional collaboration: Partner effectively with prompt engineers, designers, AI researchers, and mobile engineers

• Technical translation: Bridge technical AI concepts and user experience needs

• Analytics proficiency: SQL, Amplitude/Mixpanel, A/B testing platforms, familiarity with LLM evaluation frameworks

• Comfortable with ambiguity and building in uncharted territory

• Excited by AI conversational interfaces, tone & personality, dialogue pacing, proactive vs. reactive design

• Think in "conversation flows" and "multimodal orchestration," not just "user flows" and "screens"

• Strong opinions, weakly held about what makes AI interactions effective vs. robotic

• Passionate about crafting AI experiences that feel natural, trustworthy, and helpful

• Illustrated history of living the values necessary to Priceline:  Customer, Innovation, Team, Accountability and Trust. 

• The Right Results, the Right Way is not just a motto at Priceline; it’s a way of life. Unquestionable integrity and ethics is essential.   

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. In addition to a competitive base salary, certain roles may be eligible for an annual bonus and/or equity grant. 

The salary range for this position is $180,000- $205,000K USD.

#LI-Hybrid

#LI-VM1

Our success as one of the biggest players in online travel is all thanks to our incredible, dedicated team of talented employees. Priceliners are focused on being the best travel deal makers in the world, motivated by our passion to help everyone experience the moments that matter most in their lives. Whether it’s a dream vacation, your cousin’s graduation, or your best friend’s wedding - we make travel affordable and accessible to our customers. 

Our culture is unique and inspiring (that’s what our employees tell us). We’re a grown-up, startup. We deliver the excitement of a new venture, without the struggles and chaos that can come with a business that hasn’t stabilized.  

We’re on the cutting edge of innovative technologies. We keep the customer at the center of all that we do. Our ability to meet their needs relies on the strength of a workforce as diverse as the customers we serve. We bring together employees from all walks of life and we are proud to provide the kind of inclusive environment that stimulates innovation, creativity and collaboration.

Priceline is part of the Booking Holdings, Inc. (Nasdaq: BKNG) family of companies, a highly profitable global online travel company with a market capitalization of over $80 billion. Our sister companies include Booking.com, BookingGo, Agoda, Kayak and OpenTable. 

If you want to be part of something truly special, check us out! 

Applying for this position

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