Principal Product Manager - Pricing and Personalization (Chicago)

About the RoleWe are seeking an exceptional, AI-native Senior+ Product Manager to build and lead the intelligence and reconciliation backbone of HTS across Flights, Hotels, Cars, and Ancillaries.This role owns the systems that define pricing intelligence, supplier performance reporting, and financial truth across millions of travel transactions.You will design and scale model-driven infrastructure that continuously interprets transactional data, generates reference pricing, detects performance shifts, reconciles financial flows, and governs revenue integrity in real time.This is a foundational role at the intersection of marketplace economics, machine learning, and financial systems. You will partner deeply with Data Science and Engineering to productionize predictive models, define evaluation frameworks, manage model lifecycles, and ensure intelligence systems are measurable, adaptive, and trusted.The work you do will directly shape partner economics, supplier transparency, and HTS’s global commerce platform.What would your day-to-day look like:Own the end-to-end strategy and roadmap for pricing intelligence, supplier performance intelligence, and financial reconciliation across all travel verticals.Architect and evolve reference pricing systems leveraging predictive modeling, elasticity signals, competitive benchmarking, and real-time anomaly detection.Build the supplier intelligence layer, transforming transactional data into automated performance signals, demand insights, and pricing diagnostics.Establish and govern the canonical source of truth for revenue, margin, take rate, transactions, and cancellations across systems and partners.Design model evaluation, monitoring, and feedback frameworks, including drift detection and continuous improvement mechanisms.Drive cross-functional execution across Engineering, Data Science, Finance, Commercial, and Supply to deliver production-grade, model-integrated infrastructure.An ideal candidate has:5+ years of Product Management experience, including ownership of AI-native products and model-driven systems in production. You have built and scaled systems where AI is foundational to product behavior — not an additive feature.Hands-on experience writing prompts, designing evaluation harnesses, or prototyping with LLMs/foundation models as part of their PM workflow (not just overseeing others doing it)Strong fluency working independently with SQL and large-scale transactional datasets.Demonstrated experience operating as an AI-native PM, with hands-on ownership of model lifecycle management including problem framing, signal design, evaluation metrics (e.g., precision/recall tradeoffs, forecasting accuracy), monitoring frameworks, drift detection, and retraining strategies.Experience shipping predictive systems, anomaly detection platforms, automated decisioning infrastructure, or model-driven pricing systems at scale.Experience owning pricing systems, financial reporting platforms or marketplace intelligence tools.Deep understanding of marketplace economics, revenue mechanics, and pricing strategy.Track record of delivering complex, cross-functional systems with measurable business impact.Exceptional communicator able to operate effectively across technical, and commercial stakeholders.Bonus:Prior experience in Data Science, Engineering, or a highly technical role.Background in travel commerce, fintech, ads, or other transaction-heavy marketplace environments.Perks and benefits of working with us:Well-funded and proven startup with large ambitions, competitive salary and the upsides of pre-IPO equity packages.Unlimited PTO.Carrot Cash travel stipend.Access to co-working space on demand through FlexDesk AND Work-from-home stipend.Please ask us about our very generous parental leave, much above industry standards!.Entrepreneurial culture where pushing limits and taking risks is everyday business.Open communication with management and company leadership.Small, dynamic teams = massive impact.100% employer paid Medical, Dental and Vision coverage for employees.Access to Disability & Life insurance.Health Reimbursement Account (HRA).DCA/ FSA and access to 401k plan.More about HopperAt 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. he 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 everyone knows 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’ 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 vs if they booked just travel.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 (airlines, hotels, banks, travel agencies, etc.) 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 new 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 have millions of new installs each month. Hopper is now the #3 largest online travel agencies in North America and 70% of our app customers are Gen-Z and millennials 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!At Hopper, we leverage AI-driven tools to assist our team in efficiently reviewing applications. These tools help us assess qualifications fairly and objectively. By submitting your application, you acknowledge the use of these automated screening technologies.#LI-REMOTECompensation Range: $150K - $350KLocationWashington D.C. - Remote; Chicago - RemoteEmployment TypeFull timeLocation TypeRemoteDepartmentTravel TechCompensationSr Product Manager/ Principal Product Manager (L5-L6)The yearly total compensation for this position ranges from 150 000$ to 350 000$ USD. Base salary will be determined by candidates' relevant qualifications, knowledge, skills and work experience. Total compensation will include a solid base salary and will also include equity (options / RSUs), potentially a sign-on bonus and other potential incentives as per the perks and benefits section. $150K – $350K • Offers EquityCompensation will be determined by candidates' relevant qualifications, knowledge, skills and work experience. Total compensation will include a solid base salary and will also include equity (options / RSUs), sign-on bonus and other potential incentives.