Digital Tipping Product Lead

About Us
Think 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.

What You’ll Do

- Own the strategy, roadmap and execution for Digital Tipping across the guest tipping experience, staff onboarding and wallets, payouts, and hotel admin and reporting.

- Lead the payments and money-movement foundation: banking and payout partners, wallet funding and reconciliation, ledger accuracy, fees, and tax and compliance reporting (e.g., IRS tip reporting, PCI).

- Drive the HR and payroll integration strategy (e.g., UKG, Workday, Dayforce), turning bespoke enterprise integrations into scalable, self-serve capabilities that cut manual work for hotels and our internal teams.

- Partner with enterprise hotel brands and management companies to roll out tipping at scale, including brand-app integrations, brand standards, and complex staffing models such as contract workers.

- Grow adoption and tip volume after sale by improving staff setup completion, scan-to-tip conversion, and the number of guest touchpoints in use (QR, SMS, email, checkout, brand apps).

- Define and own the product’s key metrics, including tip volume, conversion, staff activation, payout reliability and support volume, and use data to set priorities.

- Work closely with engineering, design, finance, legal, customer success, sales and marketing to launch and scale products, and support pricing, packaging and competitive positioning.

- Improve operational stability and reduce 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 For

- 7+ years of product management experience, including owning a product end to end with real revenue and operational impact.

- Experience with payments, fintech, payroll or HR tech: money movement, payouts, ledgers and reconciliation, or compliance-heavy products.

- A track record of shipping integrations with third-party platforms, ideally HRIS or payroll systems, and making them scalable.

- Comfort working with large enterprise customers and many stakeholders, balancing custom asks against a product that scales for all customers.

- Strong analytical skills: you define metrics, dig into the data yourself, and use it to drive decisions on adoption and conversion.

- Strong leadership and communication skills, with the ability to align engineering, finance, legal and go-to-market teams.

- Proven ability to manage several complex 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.

Compensation

Target cash compensation ranges from $190,000-$240,000 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 & Benefits
We work hard to make Canary a fun, rewarding, and high-energy place to work. Here’s how we take care of our flock:
Time Off
Unlimited 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 Flexibility
Office 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 & Community
Self 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.