System Engineer I (Hybrid, 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.

About the Role

We seek a Systems Engineer I specialising in IT Operations Management (ITOM)  and IT Service Management (ITSM) to join our Corporate IT team. The ideal candidate builds workflows that keep OpenTable running, administers Okta, Google Workspace, Freshservice or other similar ticketing solutions. Proficient in Slack, Zoom, Atlassian Access, and our service desk operations. This role focuses on building and maintaining lifecycle management (LCM) automations and workflows, ensuring operational excellence, and partnering across Corporate IT to drive efficient employee lifecycle and support processes.

This is a System Engineer I role aligned with Corporate IT’s levelling, with a focus on completing well-scoped work independently, participating in Scrum team delivery, handling escalations, and contributing to steady improvements in automation and user experience under the guidance of senior team members.

Key Responsibilities:

• Build, maintain, and iterate on Freshservice ticket automations, notification templates, and support workflows (including Service Desk and Knowledge Base) to reduce handle time and improve deflection.
• Administer and support Google Workspace (groups, OUs, licensing, Drive/Chrome configuration), ensuring reliable day‑to‑day operations and adherence to configuration standards.
• Support and configure Slack and Zoom (including Zoom Rooms/webinar and related integrations), partnering with security and brand teams on compliance and approval procedures.
• Contribute to clean, up‑to‑date support knowledge (solutions/KB) and service metadata to improve ticket deflection and team consistency.
• Collaborate with ITSM/IAM on onboarding/offboarding and birthright access automations; integrate service desk workflows with identity lifecycle and downstream APIs where appropriate.
• Track and improve ticket metrics/SLAs, implement reporting, and use data to drive incremental process and automation improvements.
• Participate in the ticket queue for escalations and contribute to regular scrum delivery.

What You'll Need

• Demonstrated experience with workflow building and automation in service desk platforms and identity provider platforms (Okta, Google Workspace and Freshservice preferred; comparable tools considered).
• Hands‑on Google Workspace Admin experience (groups, OUs, policy/config, licensing) supporting a global user base.
• Practical familiarity with Slack and Zoom administration in an enterprise setting (policies, integrations, room/webinar basics).
• Intermediate scripting or automation skills (e.g., Python, PowerShell, or shell), plus comfort working with APIs and webhooks to connect tools and reduce manual work.
• Strong customer focus, clear written communication, and the ability to follow well‑defined procedures while escalating edge cases appropriately—consistent with System Engineer I expectations.
• Familiarity with AI-driven tools and technologies, including AI-based automations, chatbots and intelligent workflows, to enhance operational efficiency and end-user support.

Stand Out Skills

• Experience with Okta (admin, policy basics) and Okta Workflows to support lifecycle and access automations alongside IAM.
• Experience with Entra IDP (admin, policy, app registration basics) and conditional access policies to support lifecycle and access automations alongside IAM.
• Familiarity with Atlassian Access governance and SaaS SSO patterns.
• Experience with Google Cloud Platform (IAM administration, policy and governance)
• Exposure to asset logistics, ticket SLAs/reporting, and knowledge lifecycle processes.

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

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 located role is $95,000-$106,000 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.

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