P

Priceline

Online travel agency offering discount deals

Product Manager: Packages

Full-TimeUpdated
CA$100k - CA$120k+ Annual bonus + Equity grant
Mid
Toronto, ON, Canada
HybridHybrid: two days onsite; remaining days may be remote or in-office.
ProductProduct Management

About the job

Requirements
  • Have 3–5 years of product management experience; ecommerce or travel-related experience is preferred.
  • Have proven experience operating within a Product Operating Model and a strong grasp of Agile methodologies and cross-functional delivery.
  • Understand how to design features for different customer segments across web and native app experiences.
  • Use data to drive prioritization, define success metrics, and turn ambiguity into clear, actionable components.
  • Be comfortable integrating AI into personal workflows and product solutions, and identify opportunities to use AI to improve delivery for customers.
  • Influence stakeholders at all levels and translate complex technical constraints into clear business trade-offs.
  • Demonstrate the ability to work independently through complex products, investigate problems end to end, and drive solutions.
  • Demonstrate integrity and ethics in professional dealings.
Responsibilities
  • Define and own the long-term vision, strategy, and roadmap for the Packages team, translating market trends and customer feedback into actionable opportunities.
  • Operate within the Product Operating Model, balancing delivery of customer-facing features with technical debt remediation and platform-enabler work.
  • Lead prioritization, sequencing, and refinement of the product backlog in partnership with engineering and design leads.
  • Partner with Product Designers, UX Researchers, Marketing, and Engineering teams specializing in Elixir, Java, and Node.js to design end-to-end solutions across internal platforms and third-party supplier integrations.
  • Use big data, real-time analytics, and A/B testing frameworks to validate hypotheses and measure product performance against OKRs and KPIs.
  • Identify opportunities to use AI and automation to modernize search and booking processes, improving efficiency and personalization.
  • Lead product for the Packages Book & Service team, covering checkout, booking steps, and post-booking experiences.
  • Improve checkout clarity and trust, help customers recover from booking and payment errors, and improve trip management after purchase.
  • Seek post-booking opportunities to drive conversion and revenue across the portfolio.
  • Drive outcomes through influence and partnerships with Checkout, Flights, Hotels, Rental Cars, and Customer Care teams.
  • Support the broader Packages & Travel Services portfolio, including in-path travel protection and the Priceline credit card.
Desired Qualifications
  • Experience in ecommerce or a travel-related domain.

About the company

Priceline is an online travel marketplace that connects travelers with airlines, hotels, car rental companies, cruises, and vacation packages. It uses two business models: an agency model that earns commissions on bookings and a merchant model that buys travel services wholesale and resells them at a markup. It offers fixed-price listings and discount options such as Express Deals and Name Your Own Price, plus flexible options like free cancellations and pay-at-arrival, accessible via a mobile app. Under Booking Holdings, its goal is to help budget travelers access a wide range of options while giving consumers more negotiating power through transparent pricing and valuable deals.

Company Size

1,001-5,000

Company Stage

Series B

Total Funding

$77.4M

Headquarters

Norwalk, Connecticut

Founded

1998

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Simplify's Take

What believers are saying

  • Q2 2026 Booking Holdings revenue hit $7.35 billion, with room nights up 5%.
  • Penny users saved nearly ten minutes per trip and converted better in testing.
  • Booking Holdings raised 2026 transformation savings to $650 million, funding Priceline investment.

What critics are saying

  • FTC staff threatened a 2026 lawsuit over disclosures, fees, support, and billing.
  • Anthropic, Google Cloud, and OpenAI commoditize Penny's AI edge within months.
  • Expedia, Booking.com, and direct supplier apps squeeze Priceline's margins and traffic.

What makes Priceline unique

  • June 3, 2026 Penny turned Priceline into an agentic booking workflow.
  • Priceline owns inventory, payments, and preferences across 100-plus countries inside one conversation.
  • Booking Holdings gives Priceline scale, supplier leverage, and capital behind product iteration.

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Benefits

  • Hybrid Work Options
  • Remote Work Options

Growth & Insights and Company News

6 month growth

0%

1 year growth

0%

2 year growth

0%
PR Newswire
Jun 23rd, 2026
Americans cut alcohol, dining out to afford summer holidays despite rising costs

Priceline's 2026 State of Summer Travel Report reveals Americans are cutting back on nearly everything to fund summer holidays despite rising costs. The survey of 2,500 US adults found 79% plan to take at least one trip this summer, even though 44% say such a vacation feels out of reach. Eighty-four percent of Americans report paying more and getting less for travel, whilst 55% find it less affordable than last year. Over one-third have already cut everyday expenses to fund trips, with 83% of adults willing to give up alcohol before vacation. Parents and millennials face the most pressure, with 28% of millennials planning to spend $5,000 or more this summer. Sixty-nine percent regret past cost-cutting decisions, whilst half plan to use AI tools to find better deals.

PR Newswire
Jun 3rd, 2026
Priceline's Penny AI assistant goes fully agentic, booking trips in one conversation with Anthropic's Claude

Priceline has launched an enhanced version of Penny, its AI travel assistant, now powered by Anthropic's Claude. The agentic system allows travellers to move from trip planning to booking within a single conversation, handling complex requests like comparing flights across multiple destinations. The experience features an interactive map that updates during conversations, along with personalised recommendations called Penny's Pick and Penny's Take. Built on Priceline's proprietary AI stack, the system integrates Claude for conversational reasoning, whilst Google Cloud and OpenAI support search and voice capabilities. Penny connects to real-time inventory from thousands of partners across over 100 countries. Early testing shows travellers using Penny demonstrate higher conversion rates and save approximately ten minutes per trip compared to those calling customer support. The service now supports multiple languages.