Staff Engineer

OpenTable; Toronto; Hybrid; CAD 130,000 - 170,000; Full time

Job summary

A leading online restaurant reservation platform seeks a Staff Engineer to lead the evolution of its payments platform. This role offers a unique opportunity for an experienced professional with a strong Java tech stack and expertise in Stripe. You will be responsible for designing scalable payment infrastructure, implementing security measures, and guiding a small team. A competitive salary range of $130,000-$170,000 CAD plus benefits is offered. This position will start remotely with plans for a hybrid work environment.

Benefits

Generous paid vacation

Company-paid therapy sessions

Access to e-learning

Private health and dental insurance

Qualifications

• 5+ years of experience in payment ecosystem with Java tech stack.
• Experience with Stripe and enterprise payment platforms.
• Solid software engineering fundamentals.

Responsibilities

• Lead technical direction for payment architecture focused on Stripe.
• Design scalable payment infrastructure.
• Implement 3DS 2.0 authentication and fraud prevention.

Skills

Java tech stack

Stripe Connect

Chargeback handling

Tokenization

3D Secure (3DS)

Tools

Postgres

MongoDB

Kubernetes

Restful APIs

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 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:

• 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
• Focus on your career growth:
• 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.

At 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.

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.

Create a Job Alert

Interested in building your career at OpenTable? Get future opportunities sent straight to your email.

Apply for this job

*

First Name *

Last Name *

Email *

Phone *

Location (City) *

Resume/CV *

Enter manually

Accepted file types: pdf, doc, docx, txt, rtf

Enter manually

Accepted file types: pdf, doc, docx, txt, rtf

Education

School Select...

Degree Select...

Select...

Select...

Start date year

End date month Select...

End date year

Acknowledge/Confirm

KAYAK Software Corporation, OpenTable, Inc., their respective subsidiaries and Momondo A/S (together, ‘KAYAK and OpenTable”, “our/we/us”, or “Company”) will process your personal data in accordance with applicable data protection laws for the purposes described in our privacy notice (KAYAK (Germany) /OpenTable (Germany) andKAYAK (All Other Locations) /OpenTable (All Other Locations) ). As part of the application process KAYAK and/or OpenTable may share your personal data across our group of companies, subject to our privacy notice and applicable laws. In order to consider you for new positions, KAYAK and/or OpenTable may keep your personal data for 6 months (within the EU) and 2 years (in all other regions), unless otherwise required by applicable law.

Where do you currently reside? * Select...

Will you now or in the future require visa sponsorship? * Select...

LinkedIn Profile

Website

How did you hear about this job?

If you use a first name other than the one entered above that you would prefer we use when communicating with you, please enter it here:

If you use a last name other than the one entered above that you would prefer we use when communicating with you, please enter it here:

Have you previously worked or currently work for one of our sister brand companies?

Booking Holdings

booking.com

FareHarbor

FareHarbor US

Getaroom

KAYAK

OpenTable

Priceline

Are you legally authorized to work in Canada? Please note that we are unable to offer work sponsorship. * Select...

This role requires attendance in our office location in downtown Toronto (opening in late 2025/early 2026). Are you able to meet the requirement of attending the office 2 days a week once the office opens? * Select...