Cloud End User Technology Engineer

Odyssey Reinsurance Company (OdysseyRe) is the global reinsurance arm of Odyssey Group, one of the world’s leading providers of reinsurance and specialty insurance. OdysseyRe offers a broad range of property, casualty, and specialty reinsurance products, providing capital and risk management solutions for clients to efficiently manage economic risk through a network of branch and representative offices across North America, Latin America, EMEA (Europe, Middle East & Africa), AsiaPacific and London.

OdysseyRe is an equal opportunity employer with excellent benefits and a strong commitment to providing training and opportunities for our staff. We provide employees an innovative, enriching environment and take great pride in their career growth.

OdysseyRe is rated A+ (Superior) by AM Best and A+ (Strong) by Standard and Poor’s. Odyssey Group is a subsidiary of Fairfax Financial Holdings Limited, which is traded on the Toronto Stock Exchange under the symbol FFH.

The Cloud End User Technology and Network Infrastructure Engineer will play a critical role in maintaining and enhancing both network infrastructure and end-user computing environments. This blended role ensures the stability, security, and scalability of our network and desktop infrastructure, directly enabling global workforce productivity and operational efficiency.

Key Responsibilities

Cloud and End-User Technology:

• Enhance remote work capabilities by deploying tools and technologies for efficient global workforce productivity.
• Troubleshoot and analyze service disruptions to identify root causes and implement reliable solutions.
• Manage end-user devices, including OS and third-party patching, and implement CIS critical security controls.
• Administer Active Directory, Microsoft Entra, and endpoint management platforms such as Intune and SCCM/MECM.
• Monitor the environment proactively, establish performance baselines, and provide escalation support for L3 incidents.
• Handle escalations involving endpoint hardware, workstation applications, Windows OS, Microsoft O365, and networking issues.
• Contribute to IT infrastructure refreshes, migrations, and new office build-outs.

Network Infrastructure:

• Replace outdated network equipment at branch offices (e.g., Cisco switches and routers), including travel as required.
• Update network diagrams, inventory, and monitoring systems; reconfigure switch ports via ticketing requests.
• Respond to network incidents, perform initial troubleshooting, and ensure network health.
• Manage circuit installations, renewals, and outages, collaborating with facilities and ISP teams as needed.
• Perform quarterly software updates on network equipment, including Arista switches, Palo Alto firewalls, and Aruba SD-WAN.
• Conduct daily and weekly health checks on network equipment, ensuring optimal performance and addressing anomalies.

Preferred Qualifications and Skills:

• Education: BS/MS in Computer Science, IT, or a related field.
• Experience: 5-8 years managing network and Microsoft technologies.
• Technical Expertise:
  • Networking: Arista, Cisco, Palo Alto, Aruba, and related monitoring tools.
  • End-User Management: Microsoft Intune, Active Directory, SCCM/MECM, and Mobile Device Management.
  • Troubleshooting: Endpoint monitoring, PowerShell scripting, DNS/DHCP, Wi-Fi, and virtualization platforms.
• Soft Skills: Strong analytical abilities, excellent customer-facing problem-solving, and technical writing.
• Certifications: ITIL, CISSP, or relevant vendor certifications are a plus.

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