Staff Engineer

Summary

Join OpenTable, a leading industry player in restaurant technology, as a Staff Engineer specializing in payments. Lead the evolution of our payments platform, focusing on Stripe and other major payment providers. You will design, build, and maintain secure and scalable payment infrastructure. Collaborate with various teams to ensure seamless experiences for restaurants and diners. This remote-first role offers a hybrid schedule option in Toronto. The position requires extensive experience in payments and leadership skills.

Requirements

• 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 data

Responsibilities

• 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

Preferred Qualifications

• 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

• Work from (almost) anywhere for up to 20 days per year
• 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
• 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
• This role is eligible to be considered for an annual bonus and equity grant