Principal Product Manager – Conversational AI

🕒 August 14

🇨🇦 Canada – Remote

⏰ Full Time

🔴 Lead

✅ Product Manager

👻 Ghost score 11%

What it means: how likely this posting is sitting open without active hiring.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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Hopper

WebsiteLinkedInAll Job Openings

201 - 500 employees

🏨 Hospitality

📦 Logistics

✈️ Travel

💰 $96M Venture Round on 2022-11

Hospitality • Logistics • Travel

Hopper is a travel booking platform that offers a one-stop solution for planning trips, including flights, hotels, rental cars, and homes. The platform features advanced options such as price prediction, disruption assistance, and the Price Freeze™ feature, allowing travelers to secure deals and manage changes conveniently. Hopper is known for its mobile app availability on iOS and Android, providing a streamlined experience for its users. It serves millions of travelers worldwide, offering VIP support and various affiliate programs for partners.

📋 Description

• Own the roadmap for the customer-facing conversational agent across chat and voice • Translate enterprise partner needs into product requirements and launch decisions • Partner with Partner Solutions on implementation and onboarding • Drive daily design work in Figma, producing flows and wireframes • Build working prototypes with AI coding tools • Define quality bars covering resolution, containment, escalation correctness, and conversation quality • Specify agent behavior, tone, escalation policies, guardrails, and edge cases • Use production conversation data to iterate • Feed insights from go-to-market, Partner Solutions, and Success teams into the roadmap

🎯 Requirements

• 8+ years of product management experience • Principal- or lead-level ownership of a customer-facing product • Conversational AI, customer experience automation, or adjacent experience strongly preferred • Hands-on Figma experience producing flows and basic mocks independently • Ability to write enough code to build working prototypes without an engineer • Hands-on front-end development experience • Deep enterprise partner-facing experience, ideally in regulated industries • Data-driven approach using customer service and automation metrics • Working familiarity with LLM-based products, prompt and behavior design, AI quality practices, and failure modes

🏖️ Benefits

• Competitive salary and pre-IPO equity packages • Hopper covers 100% of group insurance premiums • Life, short-term disability, and long-term disability coverage • HSA covering eligible medical and dental expenses • Dialogue telemedicine services for employees and dependents • RRSP plan with automatic pre-tax withdrawals • Generous parental leave • Unlimited PTO • Carrot Cash travel stipend • On-demand coworking access through FlexDesk • Work-from-home stipend