Principal Product Manager- Conversational AI

About the Role
HTS Assist is Hopper's agentic AI assistant for travel, resolving real customer issues like flight changes, cancellations, refunds, and bookings over chat and voice for some of the largest travel brands and enterprises in the world. As Principal Product Manager, you will own the customer-facing agent end to end: the conversations, the interface, and the experience our partners put in front of millions of travelers. This is a deliberately design-leaning role, and you will be the day-to-day design decision-maker, shaping flows and interfaces directly in close partnership with partner design teams and our in-house designer.

What would your day-to-day look like

• Own the roadmap for the customer-facing conversational agent across chat and voice, from intent coverage and conversation design to the interfaces partners embed in their apps and websites

• Engage enterprise partners through discovery, requirement shaping, and launch decisions, translating partner asks into product choices that keep one product serving many partners

• Partner with Partner Solutions on implementation and onboarding

• Drive design daily, working hands-on in Figma to produce flows and wireframes, and partner with design on high-fidelity and production assets

• Build working prototypes using AI coding tools where they beat a written spec, to test conversation flows and interface ideas

• Define and defend quality bars with the evaluation team, covering resolution rate, containment, escalation correctness, and conversation quality

• Specify agent behavior in detail, including resolution, tone, escalation policy, guardrails, and edge cases, and iterate from production conversation data

• Stay close to GTM, Partner Solutions, and Success teams, feeding what the field learns back into the roadmap

An ideal candidate has

• 8+ years of product management experience, including principal or lead-level ownership of a customer-facing product, with conversational AI, customer experience automation, or an adjacent space strongly preferred

• Design fluency, comfortable manipulating design files and producing flows and basic mocks solo in Figma, having operated as a de facto design lead on a lean team

• The ability to write enough code to get a prototype working without waiting on an engineer, treating AI tools as a normal part of how they build

• Hands-on front-end experience, having built or shipped web front ends and able to engage engineers credibly

• Deep partner-facing experience with enterprise clients, ideally in regulated industries, shaping requirements and launch decisions at the product level

• A data-driven approach grounded in customer service and automation metrics, including resolution, containment, CSAT, and escalation quality

• Working familiarity with LLM-based products, including prompt and behavior design, AI quality practices, and their failure modes

Perks and benefits of working with us

• Well-funded and proven startup with large ambitions, competitive salary and upsides of pre-IPO equity packages

• Hopper covers 100% of the premiums for the group insurance plan

• Hopper offers life, short term and long term disability coverage

• HSA that covers eligible medical and dental expenses

• All employees and dependents have access to Dialogue's telemedicine services, anytime, anywhere

• All employees have access to an RRSP plan with automatic pre-tax withdrawals per pay

• Please ask us about our very generous parental leave, much above industry standards

• Unlimited PTO

• Carrot Cash travel stipend

• Access to co-working space on demand through FlexDesk and a work-from-home stipend

• Entrepreneurial culture where pushing limits and taking risks is everyday business

• Open communication with management and company leadership

• Small, dynamic teams with massive impact

About Hopper
At Hopper, we are on a mission to become the leading travel platform globally, powering Hopper's mobile app, website and our B2B business, HTS (Hopper Technology Solutions). By leveraging massive amounts of data and advanced machine learning algorithms, Hopper combines its world-class travel agency offering with proprietary fintech products to bring transparency, flexibility and savings to travelers globally. We have developed several unique fintech solutions that address everything from pricing volatility to trip disruptions, helping people travel better and save more on their trips.

The Hopper platform serves hundreds of millions of travelers globally and continues to capture market share around the world. The Hopper app has been downloaded over 120 million times and has become largely popular among younger travelers, with 70% of its users being Gen Z and millennials.

While many know us as the Gen Z and Millennial travel app, Hopper has evolved to become much more than that. In recent years, we've grown into a travel fintech provider, commerce platform, and global travel agency that powers some of the world's largest brands.

Through HTS, our B2B division, the company supercharges its partners' direct channels by integrating our fintech products on their sites or powering end-to-end travel portals. Today, our partners include leading travel brands like Capital One, Nubank, Air Canada, and many more.

Here are just a few stats that demonstrate the company's recent growth: billions of dollars worth of travel and travel fintech are sold through Hopper and HTS's channels every year. Our fintech products, including Cancel for Any Reason and Flight Disruption Assistance, have exceptionally strong CSAT because the terms are always clear and customers receive instant, no-questions-asked resolutions. Almost 30% of our app customers purchase at least one fintech product when making a booking, and consumers are 1.6x more likely to repurchase if they add fintech to their booking versus booking travel alone.

Given the success of its fintech products, Hopper launched a B2B initiative, HTS (Hopper Technology Solutions), which represents more than 75% of the business. Through HTS, any travel provider, including airlines, hotels, banks, and travel agencies, can integrate and seamlessly distribute Hopper's fintech or travel inventory on their direct channels. As its first HTS partnership, the company partnered with Capital One to co-develop Capital One Travel, a travel portal designed specifically for cardholders. Other HTS partners include Air Canada, Uber, CommBank, Nubank, Flair Airlines and many more.

Hopper has been named the #1 most innovative company in travel by Fast Company. Hopper has been downloaded over 120 million times and continues to see millions of new installs each month. Hopper is now the #3 largest online travel agency in North America, and 70% of our app customers are Gen Z and millennial travelers.

Hopper has raised over $750 million USD of private capital and is backed by some of the largest institutional investors and banks in the world. HTS is primed to continue its growth as the leading travel ecommerce provider in a $1 trillion online shopping category. The Hopper app and website will also continue to be the preferred travel provider for Gen Z and Millennials.

Come take off with us!
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