Principal Product Manager- Conversational AI

Compensation

The annual total compensation for this position ranges from $250,000 to $300,000 CAD. Base salary will be determined by candidates' relevant qualifications, knowledge, skills and work experience. Total compensation will include base salary and equity (options), other potential incentives as per the "perks and benefits" section.

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.

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
• Set the product bar for voice specifically, covering latency, turn-taking, barge-in handling, localization, realtime voice and ASR/TTS quality
• 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 across both chat and voice
• 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 direct experience shipping voice-based conversational products such as IVR, voice bots, or contact center voice automation
• Hands-on ownership of a production voice product, not only chat or text-based conversational AI, with working knowledge of ASR/TTS tradeoffs, latency budgets, and turn-taking or barge-in design
• Design fluency, comfortable manipulating design files and producing flows and basic mocks solo in Figma
• 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