Senior M365 Messaging Specialist

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior M365 Messaging Specialist based in Canada. Join a global Collaboration and IT team responsible for one of the organization’s most critical communication services, supporting more than 100,000 mailboxes worldwide. You’ll serve as a senior technical expert responsible for the architecture, security, reliability, and continuous improvement of Microsoft messaging environments. The role combines hands-on engineering with complex troubleshooting, automation, compliance, and large-scale migration initiatives. You’ll work across Microsoft 365, Exchange Online, hybrid Exchange, Proofpoint, Defender for Office 365, and related security technologies. Your expertise will help protect enterprise communications while ensuring reliable email delivery and a strong user experience. You’ll also provide Tier 3 support, mentor junior engineers, and guide technical teams through complex messaging challenges. This remote Canadian role offers the opportunity to influence global infrastructure while working on high-impact collaboration and integration projects. This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Senior M365 Messaging Specialist based in Canada. Join a global Collaboration and IT team responsible for one of the organization’s most critical communication services, supporting more than 100,000 mailboxes worldwide. You’ll serve as a senior technical expert responsible for the architecture, security, reliability, and continuous improvement of Microsoft messaging environments. The role combines hands-on engineering with complex troubleshooting, automation, compliance, and large-scale migration initiatives. You’ll work across Microsoft 365, Exchange Online, hybrid Exchange, Proofpoint, Defender for Office 365, and related security technologies. Your expertise will help protect enterprise communications while ensuring reliable email delivery and a strong user experience. You’ll also provide Tier 3 support, mentor junior engineers, and guide technical teams through complex messaging challenges. This remote Canadian role offers the opportunity to influence global infrastructure while working on high-impact collaboration and integration projects. Accountabilities Lead the architecture, deployment, configuration, maintenance, and continuous improvement of Microsoft Exchange Online and hybrid Exchange environments. Manage and optimize Proofpoint technologies, including Email Protection, Threat Response, TAP, and Data Loss Prevention policies. Administer and maintain messaging security technologies including Microsoft Defender for Office 365. Configure and manage email authentication and security standards, including SPF, DKIM, DMARC, and TLS. Act as a subject matter expert for email routing, mail flow, delivery troubleshooting, message tracing, and complex messaging incidents. Lead messaging migrations and integrations, including initiatives associated with organizational growth, acquisitions, and technology consolidation. Establish and implement best practices for email retention, legal holds, eDiscovery, and messaging compliance. Develop and maintain PowerShell automation for Microsoft 365 administration, system management, reporting, and operational efficiency. Provide advanced Tier 3 technical support and guidance for complex messaging issues. Mentor junior engineers and provide technical guidance to IT support teams. Identify opportunities to improve messaging services through new technologies, automation, architecture improvements, and industry best practices. Produce clear technical documentation covering configurations, procedures, troubleshooting processes, and operational standards. Collaborate with cross-functional technology teams to ensure messaging environments remain secure, reliable, scalable, and aligned with business requirements. Requirements At least 5 years of professional experience architecting, administering, and maintaining Microsoft messaging and collaboration solutions. Bachelor’s degree in Computer Science, Information Technology, or a related discipline, combined with relevant professional experience; equivalent practical experience may also be considered. Deep expertise with Microsoft Exchange Online and hybrid Exchange environments. Strong knowledge of Microsoft 365 administration and messaging architecture. In-depth understanding of email authentication protocols including SPF, DKIM, and DMARC. Hands-on experience configuring and managing secure email gateways, particularly Proofpoint or comparable enterprise messaging security platforms. Experience with Microsoft Defender for Office 365 and Microsoft 365 security and compliance capabilities. Strong knowledge of email encryption technologies and secure mail-flow configurations. Advanced PowerShell scripting skills, particularly for Exchange and Microsoft 365 administration, automation, reporting, and system management. Strong understanding of email routing, mail-flow policies, message tracing, and delivery troubleshooting. Experience with email retention, legal hold, eDiscovery, and compliance requirements. Demonstrated ability to troubleshoot complex technical problems and identify effective, scalable solutions. Excellent communication, collaboration, and technical documentation skills. Ability to provide technical leadership and mentorship to junior engineers and support teams. Comfortable working independently in a distributed, global environment. Willingness to travel internationally or domestically up to 10% as required. Benefits Salary: Annual compensation range of $125,000–$135,000 CAD , subject to applicable factors and potential future adjustments. Bonus opportunity: Eligibility for bonus or incentive compensation. Remote work: Fully remote work arrangement from within Canada. Healthcare: Comprehensive medical, dental, and vision coverage for eligible employees. Retirement: RRSP benefits for eligible employees. Paid time off: Comprehensive paid time-off programs. Global impact: Opportunity to support a critical messaging environment serving more than 100,000 mailboxes worldwide. Professional growth: Exposure to large-scale Microsoft 365, Exchange, email security, compliance, automation, and migration initiatives. Technical leadership: Opportunity to influence architecture, establish best practices, mentor engineers, and drive continuous improvement. Flexible working: A remote-friendly environment designed to support flexibility and sustainable working arrangements. Inclusive culture: Commitment to equal opportunity, diversity, accessibility, and an inclusive workplace where different perspectives are valued. How Jobgether works: We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best! Why Apply Through Jobgether? Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. 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