Senior M365 Messaging Specialist

Triwill Group; Canada; Hybrid; CAD 110,000 - 160,000; Full time

Job summary

Triwill Group seeks a Senior M365 Messaging Specialist based in Canada to lead the architecture, security, and reliability of Microsoft messaging environments across 100,000+ mailboxes worldwide.

You will combine hands-on engineering with complex troubleshooting, automation, and large-scale migration initiatives while mentoring junior engineers and providing Tier 3 support.

Qualifications

• Senior technical expert for Microsoft messaging environments in an enterprise.
• Experience with large-scale migration and security enhancements.
• Hybrid Exchange and Exchange Online administration.

Responsibilities

• Architect, secure, and improve messaging infrastructure.
• Lead complex troubleshooting and automation initiatives.
• Collaborate across Microsoft 365, Exchange Online, and related security technologies.

Skills

Microsoft 365

Exchange Online

Hybrid Exchange

Automation

Troubleshooting

Security

Migration

Mentoring

Proofpoint

Defender 365

Tools

Proofpoint

Defender for Office 365

Job description

Description:

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.