Company: OpenTable

Location: Toronto, ON

Expected salary: $130000 – 170000 per year

Job date: Wed, 23 Jul 2025 01:37:52 GMT

Job description: This will be a remote role to start, with plans to transition to hybrid in-office 2x/week located in downtown Toronto.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 empowers restaurants to focus on what matters most – their team, their guests, and their bottom line – while enabling diners to discover and book the perfect restaurant for every occasion.Every employee at OpenTable has a tangible impact on what we do and how we do it. You’ll also be part of a global team and its portfolio of metasearch brands. Hospitality is all about taking care of others, and it defines our culture.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.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 the payments 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 dataBonus 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 experiencesBenefits and Perks:

• Generous paid vacation + time off for your birthday
• 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
• Annual company-wide week off a year – the whole team fully recharges (and returns without a pile-up of work!)
• Paid parental leave
• 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
• 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.Work Environment & FlexibilityAt OpenTable, we pride ourselves on fostering a global and dynamic work environment. As a team member with us, you will benefit from a schedule tailored to accommodate a global workforce operating across multiple time zones. While the majority of your responsibilities may align with conventional business hours, there will be instances where you are expected to manage communications – via calls, Slack messages, or emails – outside of regular working hours to effectively collaborate with international colleagues, respond to restaurant partners, and/or address urgent matters. OpenTable will always abide by and consider local laws and regulations.InclusionWe’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.