With millions of diners, 60,000 restaurant partners and 25+ years of experience, OpenTable, part of Booking Holdings, Inc. (NASDAQ: BKNG), is an industry leader with a passion for helping restaurants thrive. Our world-class technology enables restaurants to focus on what matters most – their team, their guests, and their bottom line – while empowering diners to discover and book the perfect restaurant for every occasion.

We believe hospitality is all about taking care of others and that ethos defines our culture. Every employee at OpenTable has a tangible impact, contributing to a global team that includes our sister brand KAYAK and its portfolio of metasearch products.

The Opportunity:

We’re looking for a Staff Engineer with deep expertise in the payments domain to help lead the evolution of our payments platform. This role is ideal for someone with extensive experience in Stripe (especially Stripe Connect), FreedomPay, CardConnect, and other major payment providers. Knowledge of 3D Secure (3DS) flows, chargeback handling, tokenization, and real-time authorization is essential.

You’ll work closely with product, design, and engineering teams to build secure, scalable, and delightful payment experiences for both restaurants and diners around the world.

This is a remote-first role, with an eventual hybrid schedule (2x/week) planned for our downtown Toronto, Canada office.

In this role, you will:

Lead technical direction for payment integrations and architecture, with a primary focus on Stripe (Connect, Elements, PaymentIntents, webhooks, reconciliation, etc.)
Design and build flexible, scalable payment infrastructure that supports integrations with FreedomPay, CardConnect, and other processors
Implement and evolve 3DS 2.0 authentication flows, fraud prevention strategies, and chargeback mitigation techniques
Collaborate with internal and external partners on PCI compliance, tokenization, and secure card handling
Guide a small team of engineers focused on reliability, security, and performance of our payment services
Ensure seamless diner and restaurant experiences through robust orchestration across payment providers
Contribute to payment products across web and mobile, including prepaid experiences, deposits, and CC holds
Define logging, observability, and SLA metrics for payments (ELK, Grafana, custom dashboards)
Mentor teammates and drive cross-functional alignment on payment-related roadmaps

We’re excited about you if you have:

5+ years of experience working with Java tech stack in thepayments ecosystem, with strong focus on Stripe (especially Stripe Connect, webhooks, disputes, transfers, onboarding)
Experience integrating with FreedomPay, CardConnect, or similar enterprise payment platforms
Deep understanding of 3D Secure protocols, tokenization, and chargeback workflows
Solid software engineering fundamentals and experience building with Java, Postgres, K8s, MongoDB, Restful APIs
Familiarity with observability tools (e.g., StatsD, Grafana, ELK stack)
Strong leadership and communication skills, with a track record of driving cross-team initiatives
Understanding of PCI-DSS, secure key management, and best practices for storing/transmitting sensitive data

Bonus Points:

You’ve launched products that handled high-volume payments and know the edge cases inside out
You’ve worked with restaurant tech, hospitality systems, or marketplace platforms
You enjoy pairing great software with delightful customer experiences

Benefits and Perks

Work from (almost) anywhere for up to 20 days per year
Focus on mental health and well-being:

Company-paid therapy sessions through SpringHealth
Company-paid subscription to HeadSpace
Company-wide week off a year - the whole team fully recharges (and returns without a pile-up of work!)

Paid parental leave
Generous paid vacation + time off for your birthday
Paid volunteer time
Focus on your career growth:

Development Dollars
Leadership development
Access to thousands of on-demand e-learnings

Travel Discounts
Employee Resource Groups
20 days of paid time off upon start
Private health and dental insurance
Life and Disability insurance

There are a variety of factors that go into determining a salary range, including but not limited to external market benchmark data, geographic location, and years of experience sought/required. The range for this Canada based role is 130,000-170,000 CAD.

We offer a competitive base salary and benefits including: health benefits; flexible spending account; retirement benefits; life insurance; paid time off (including PTO, paid sick leave, medical leave, bereavement leave, floating holidays and paid holidays); and parental leave benefits. This role is eligible to be considered for an annual bonus and equity grant.

Inclusion

We’re committed to creating a workplace where everyone feels they belong and can thrive. We know the best ideas come when we bring different voices to the table, so we're building a team as dynamic as the diners and restaurants we serve—and fostering a culture where everyone feels welcome to be themselves.

If you need accommodations during the application or interview process, or on the job, we’re here to support you. Please reach out to your recruiter to request any accommodations.