System Engineer I

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 System Engineer I specializing in device management to join our Corporate IT team. The ideal candidate administers macOS and Windows device management systems, has strong scripting expertise, maintains compliance and security policies, and handles a variety of endpoint management tasks in their current or prior roles. Responsibilities include improving endpoint lifecycle management, security, and metrics, as well as addressing incidents related to compliance, patching, and integration issues.

The System Engineer (EPM) will lead projects, provide strategy, ensure system reliability and mentor team members on EPM systems. The ideal candidate demonstrates technical confidence, communication mastery and tactical acumen.

If you’re solution‑oriented, comfortable learning new technology, and passionate about continuous improvement – we are looking for someone like you.

Responsibilities

• Global Fleet Management of macOS & Windows Devices
• Security and Compliance Policy Management
• Integration and Automation with directory systems and third‑party tools
• Asset and Metrics Management
• Planning & Contributing to Agile Scrum Team

Minimum Qualifications

• Minimum of 5 years of relevant hands‑on experience implementing and maintaining MDM products like Intune, Jamf, or Iru.
• Proficiency in Application distribution, Security controls and compliance, User and Device management, Tenant Administration.
• Hands‑on experience with Entra ID, and Okta.
• Strong working experience with the standard operating systems, including Windows, macOS, Linux, or Unix.
• Strong understanding of compliance and security policies.
• Experience in vulnerability and patch management, and device posture assessments.
• Excellent problem‑solving skills and ability to handle technical incidents.
• Strong communication skills and ability to work collaboratively with cross‑functional teams.
• Superior troubleshooting skills, resourcefulness, desire, and ability to learn new technologies.
• Strong analytical and communication (both oral and written) abilities.
• Dedicated team player able to build consensus and negotiate.
• Ability to manage simultaneous assignments and priorities.

Preferred Qualifications

• Jamf 400 or equivalent Certifications for Systems Administrators, such as Microsoft Certified Solutions Expert.
• Experience using Intune MDM / Google MDM / Jamf MDM / Iru MDM.
• Patch Manager Plus or similar Patch Management tools.
• Okta workforce identity certifications, such as Okta Certified Administrator.
• Experience with cloud‑based VDI solutions.
• Familiarity with Apple Business Management and Apple Enterprise Services.
• macOS Shell Expertise
• Strong scripting experience in Python, Shell, or similar.
• Networking

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:
  • 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

Compensation

The expected range of compensation for this position based in Toronto, Canada, including commission and/or bonuses is $70,000 - $90,000 CAD. 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; 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 Schedule & 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.

Accommodations

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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