Cloud Engineer - Core Infrastructure

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 Core Infrastructure Team at OpenTable is responsible for building, maintaining, and evolving the foundational technology stack that supports all environments, from development to production. Their work focuses on our cloud infrastructure (AWS and GCP) and the modernization of our on-premise platforms, including virtualization, shared storage, and identity systems.

Automation is a key focus, with tools like Ansible, Puppet, and custom solutions streamlining provisioning and maintenance. Strategically, the team is focused on improving availability, resiliency, efficiency, and security. Major initiatives include modernizing our cloud infrastructure, automating operational tasks, and evaluating new technologies, with a strong focus on leveraging AI tools for troubleshooting and automation. The team primarily serves internal engineering groups, ensuring robust, stable, and scalable infrastructure for OpenTable’s products and services.

The Role

In this role, we are seeking someone experienced in modernizing legacy software stacks for the cloud, with a primary focus on AWS. You will help the DBA team migrate traditional database workloads—such as MongoDB and PostgreSQL—to cloud environments and support internal teams in their efforts deploying and operating Kubernetes in the cloud.

A key part of this role involves integrating with artificial intelligence platforms (such as Bedrock and Vertex AI) to enhance our operations and automation capabilities.

While we also maintain on-prem hypervisor infrastructure, your objective will be to automate its routine operational tasks via APIs to reduce manual toil , freeing up time for cloud and AI initiatives. You will develop solutions that interact with these platforms’ APIs. Experience with Linux operating systems is a huge plus.

In this role, you will be responsible for:

• Managing and optimizing cloud infrastructure in AWS and GCP, including service deployment and resource utilization
• Leading the evaluation and integration of new technologies, especially AI platforms (like Bedrock and Vertex AI), to improve infrastructure operations
• Developing and maintaining automation and tooling for provisioning, configuration, and operational tasks (using tools like Ansible, Puppet, Terraform, Packer, and custom solutions) to reduce manual toil
• Implementing and maintaining disaster recovery strategies for critical services, including cross-datacenter and cloud-based replication
• Automating the administration of virtualization platforms, including VM provisioning, balancing, and patch management
• Collaborating with security, networking, and data platform teams to ensure infrastructure reliability, scalability, and compliance
• Overseeing shared storage solutions, backup strategies, and storage protocol migrations
• Participating in on-call rotations and incident response for infrastructure-related issues

Please apply if:

• You love tackling new things you’ve never been exposed to before and enjoy evaluating new technologies
• You know how to work with AI to write code and troubleshoot
• You have a solid foundation in scripting languages and APIs
• You love a challenge and we will give you unexpected goals that will stretch your abilities
• You’ve worked closely with Security teams and you're familiar with their tools

Required Skills:

• 3-5 years AWS Experience (certification preferred, Solutions Architect Associate minimum)
• Familiarity with aws cli commands
• 5 years scripting experience (priority is bash, go, powershell, python)
• Configuration management (puppet, ansible, terraform)
• Basic Github experience
• Linux experience (preferably Ubuntu or Debian)

Preferred but not required:

• Google Cloud Platform (certifications preferred)
• You’ve deployed services in Kubernetes before
• Experience with AI platforms (Bedrock, Vertex AI)
• Experience with identity providers (okta, AD, or anything providing OIDC/SAML)
• 3-5 years experience with on-prem hypervisors (VMware/Proxmox)
• 3-5 years experience with Shared Storage (Netapp)

Benefits:

• 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 Toronto, Canada based role is $100,000 - $120,000 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 & 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.