Senior Digital Tipping Product Manager

New York, NYProduct /Full Time /HybridAbout UsThink about your last hotel stay. Did you skip the front desk line with mobile check-in? Message the staff for extra pillows? Order a late-night snack with a tap on your phone? Then you’ve likely run into Canary in the wild.Canary Technologies is the leading agentic AI platform for hotel and guest management, powering the digital infrastructure for more than 20,000 hotels in 125+ countries. The world's most renowned hospitality brands, including Marriott International, Four Seasons and Wyndham Hotels & Resorts, partner with us to increase revenue, improve operations and elevate the guest experience.We’ve executed the largest deployment of autonomous AI systems in hospitality, building technology that fundamentally redefines how guests and hotels interact. It’s made us one of the top-funded hotel technology companies in the world, with nearly $200M raised to date.Canary has been recognized as a 2024 and 2025 Deloitte Technology Fast 500 company, Inc. 5000 fastest-growing company, and swept the 2026 HotelTechAwards, including Best Place to Work, #1 Guest Experience Platform, and the Hotelier’s Choice Award. We’re scaling our team to bring innovation to life faster than ever.We're growing quickly, and we're looking for people who are passionate about their work, want to grow with us and are ready to take on more responsibility along the way. We value rigor and velocity in equal measure: high standards, fast pace, real ownership. If that's the environment you're looking for, this is the place for you.Come join us! Let’s shape the future of hospitality together.About the RoleWe’re looking for a Senior Product Manager to drive Canary’s Digital Tipping product, the award-winning platform that lets hotel guests tip and thank staff from their phones. Housekeepers, valets, bell staff and others have long missed out on tips because guests no longer carry cash. Digital Tipping changes that and puts meaningful income and recognition in the hands of the people who make hotel stays great. Tip volume has more than tripled year over year, and we’ve been named Best Digital Tipping Solution in the HotelTechAwards three years running.This role sits where guest experience, payments and workforce systems meet. A guest scans a QR code or taps a link and tips in seconds. Behind that moment, money has to move accurately and in compliance. It has to reach staff through digital wallets, bank accounts or payroll, and it has to stay in sync with the HR and payroll systems that hotels and management companies run on. Working closely with Product leadership, you’ll own the roadmap and delivery across that loop, from the guest’s first tap to the payout in a staff member’s account.What You’ll DoOwn the roadmap and day-to-day execution for Digital Tipping, in partnership with Product leadership, across the guest tipping experience, staff onboarding and wallets, payouts, and hotel admin and reporting.Drive payments and money-movement work with engineering and finance: payout partner integrations, wallet funding and reconciliation, ledger accuracy, fees, and tax and compliance reporting (e.g., IRS tip reporting, PCI).Ship and improve HR and payroll integrations (e.g., UKG, Workday, Dayforce), helping move bespoke enterprise integrations toward repeatable, self-serve capabilities.Partner with customer success and sales on enterprise rollouts with hotel brands and management companies, including brand-app integrations, brand standards and complex staffing models such as contract workers.Run initiatives and experiments to grow adoption and tip volume: staff setup completion, scan-to-tip conversion, and guest touchpoints in use (QR, SMS, email, checkout, brand apps).Track and report on the product’s key metrics, including tip volume, conversion, staff activation, payout reliability and support volume, and use the data to inform priorities.Write clear requirements and work daily with engineering and design to ship high-quality features, while keeping finance, legal and go-to-market teams aligned on launches.Identify and fix sources of operational friction and support load so the product scales without adding manual work.Conduct research with guests, hotel staff, finance and HR teams, and hotel leadership to understand their needs and the regulations around tipping.What We’re Looking For5+ years of product management experience, including owning a product area or major features with measurable business impact.Experience with payments, fintech, payroll or HR tech, such as money movement, payouts, ledgers and reconciliation, or compliance-heavy products.Experience shipping integrations with third-party platforms; HRIS or payroll integrations a strong plus.Comfort working with enterprise customers and cross-functional stakeholders, and good judgment about when a custom request belongs in the core product.Strong analytical skills: you’re comfortable defining metrics, pulling and analyzing data yourself, and using it to make decisions.Clear written and verbal communication, with the ability to keep engineering, finance, legal and go-to-market partners aligned.Ability to manage several projects at once and prioritize in a fast-paced environment.Nice to have: hospitality or frontline-workforce experience, or experience with B2B2C products serving businesses, their employees and consumers at once.CompensationTarget cash compensation ranges from $165,000-$200,000 including a fixed annual salary and a performance-based bonus paid quarterly.This role also includes a stock option grant, subject to board approval.Actual compensation will be commensurate with the candidate's skill level, experience, and specific work location.Perks & BenefitsWe work hard to make Canary a fun, rewarding, and high-energy place to work. Here’s how we take care of our flock:Time OffUnlimited PTO: Take the time you need to truly rest and recharge.Holidays + Canary Days: Standard holidays plus monthly company-wide days off for a guaranteed long weekend.Birthday Holiday: A dedicated day off to celebrate you!Travel & Office FlexibilityOffice Exchange: A travel stipend to visit the team in person at our SF, NY, or Dallas hubs.Canary Hotel Experience: Staying at a Canary hotel? We’ve got you covered with a credit toward your stay.Preferred Hotels Discount: Enjoy a minimum 30% off the best available rate at select partner hotels globally.Growth & CommunitySelf Improvement Club: A monthly budget to help you smash your personal goals.Professional Development: Level up your career with a dedicated learning stipend to fuel your skills and cross-functional connection.Referral Program: Help us grow the flock and score a cash bonus for successful hires.Canary Technologies is an equal opportunity employer. We recruit, employ, train, compensate and promote talent regardless of race, religion, ethnicity, national origin, citizenship, gender, gender identity, sexual orientation, age, veteran status, disability, genetic information or any other protected characteristic.We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.