Senior Messaging and Microsoft 365 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.

Job Title: Senior Messaging and Microsoft 365 Engineer 

Overview: As a Senior Microsoft Technology Engineer, you will ensure the stability, security, and scalability of our messaging and Microsoft 365 infrastructure. You will be pivotal in supporting both local and remote workforces by enhancing operational efficiency through effective email, Entra, and Microsoft 365 services. 

Key Responsibilities: 

• Architect, administer and optimize Exchange Online, Entra, and Azure AD services. 

• Support management, configuration, deployment, testing, and operations of the Messaging Platform & Systems. 

• Respond to escalated incidents and service requests for email and directory services. 

• Implement and support identity management solutions for security and compliance. 

• Coordinate and run test cases in development environments along with documenting and reporting on the results of those tests. 

• Plan and coordinate updates, outages, maintenance windows, and any other activities that could impact the availability of the messaging system. 

• Design and plan processes and procedures that increase system reliability and availability; establish, test, and review disaster recovery policies and procedures. 

• Maintain and optimize system performance and efficiency through monitoring, analysis, and performance tuning, maintaining documentation. 

• Lead strategic projects for improving email, Entra, and M365 services. 

• Ensure system security, scalability, and compliance with best practices and regulations. 

• Provide expert troubleshooting and support for Microsoft 365 services, including mail flow, Teams, and Entra. 

• Design, lead , and support migrations for legacy on-premises technologies associated with Microsoft foundational services like messaging and directory and file shares. 

• Support ongoing security initiatives to improve foundational Microsoft technologies. 

Required Skills & Qualifications: 

• 5-8 years of strong experience with core Microsoft technologies (Entra, M365, Windows Server, Exchange). 

• Proficiency in Microsoft 365 administration, including Exchange Online, SharePoint, Teams, and Microsoft Endpoint Manager. 

• Expertise in Entra, including user provisioning, SSO, and hybrid configurations. 

• Strong PowerShell scripting skills for automation and system troubleshooting. 

• Experience with email security protocols (SPF, DKIM, DMARC) and mail flow troubleshooting. 

• Knowledge of Intune for mobile device management and MDM policies. 

• Familiarity with Microsoft Security tools, including Defender for Office 365 and Advanced Threat Protection. 

Technologies and Expertise: 

• Advanced configuration of Microsoft 365 services and tenant management. 

• Experience with hybrid Exchange configurations and complex mail flow setups. 

• Entra, AAD Connect, and identity synchronization. 

• Familiarity with DNS, VPN, and networking fundamentals. 

• Knowledge of monitoring tools (Azure Monitor, Log Analytics) and ticketing systems (ServiceNow, AdminDroid). 

• Experience in backup and recovery (Rubrik, Veeam). 

We are an E-Verify employer - all hired positions require successfully passing an E-Verify Check.  

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