Principal Software Engineer - Agentic Engineering Platform

Title: Principal Software Engineer - Agentic Engineering Platform Location: Toronto, Canada

With millions of diners, 70,000+ 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.

About the job

As a Principal Engineer, you'll be a founding member of OpenTable's Agentic Engineering Platform team within Product Engineering, rethinking how software gets built. Our goal is to redesign the full product delivery workflow so people and AI agents can work together in shared team spaces, automate more of the work, and reduce the total cost of delivery. Today, fragmented context, inconsistent standards, and legacy infrastructure limit what agents can complete on their own. You'll build shared cloud agents and tools that connect company knowledge and engineering systems, with the testing, review, and rollout controls needed to use them safely. Working directly with product engineering teams, you'll help turn advances in AI into ways of working that let OpenTable take on more projects.

Responsibilities

• Identify consequential bottlenecks in how teams deliver software. Use data and direct observation to choose valuable problems, define success, and lead the work through adoption.
• Design, build, integrate, and operate shared cloud agents and developer tools that connect AI models with company knowledge, codebases, APIs, and engineering systems, giving agents the context they need to complete useful work.
• Improve the full workflow across planning, implementation, testing, review, rollout, and production feedback. Question unnecessary steps and build automation that makes human and agent collaboration more effective.
• Work directly with product engineering teams to learn their domains, pilot solutions, and respond to feedback. Package tools, context, and guidance so teams can use them independently.
• Make unattended agent work dependable through permissions, isolated execution, automated testing and review, failure recovery, and cost controls. Set rollout checks based on risk, and record agent activity and outcomes so teams can trace work from request through production.
• Test new AI capabilities in short experiments and act with urgency. Measure delivery time, quality, review effort, and total cost; share what you learn and stop or replace approaches when the evidence changes.

Minimum Qualifications

• 8+ years of software engineering experience, including independently delivering and operating production systems used by others, making technical decisions, debugging failures, and working across unfamiliar codebases, APIs, databases, and cloud services.
• Deep understanding of API design, service-oriented architecture, scalability, and security.
• Strong proficiency with current AI coding tools such as Claude, Codex, or Cursor, and sound judgment about context management, model selection, and limits on what agents can do without human review.
• Ability to reason from first principles, learn an unfamiliar business domain, and turn an ambiguous problem into a useful experiment and a working solution.
• Evidence of helping other engineers adopt a tool or way of working through listening, collaboration, clear communication, and follow-through.

Preferred Qualifications

• Experience building and deploying agents and shared engineering tools.
• Production experience with cloud infrastructure, service identity, permissions, isolated execution environments, and distributed systems.
• Experience with automated testing, evaluations of agent behavior, tracing, and observability tools.
• Experience taking a prototype into sustained use across multiple teams, with evidence of improvements to delivery, reliability, or cost.
• Experience learning and improving complex existing products, particularly in marketplaces, booking, payments, or other transaction-heavy domains.

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
• Annual 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
• Private health and dental insurance
• Life and Disability insurance

The best connections happen face-to-face, whether you’re sitting down to dinner or having coffee with a coworker. That’s why OpenTable has adopted a hybrid workplace model. This role aligns with that approach, with an expectation of coming into the office two days a week—giving employees the best of both worlds: in-person collaboration and flexibility.

There are a variety of factors that go into determining a compensation range, including but not limited to external market benchmark data, geographic location, and years of experience sought/required.

We offer a competitive base salary and benefits including: health benefits, 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 & Flexibility

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.

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