Our client is an established, Winnipeg-based IT Managed Services provider that's spent nearly three decades acting as the technology backbone for businesses across healthcare, finance, legal, and other compliance-heavy sectors. They're looking to add a Tier 3 Security & Microsoft 365 Specialist to their team — someone who treats security as their primary craft, with Microsoft 365 as the environment they operate inside, not just a system they administer.
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This role isn't about ticket-driven M365 support. The ideal person can walk into an unfamiliar client tenant, diagnose what's broken or exposed, fix it properly, and then explain the "why" to a business owner who isn't technical. They're also the person clients count on when something goes seriously wrong — the calm, capable presence during an active security event.
Technical skill opens the door here, but relationship skill is what makes someone succeed long-term. This person will regularly be the one talking a stressed client through a live incident, so staying composed and communicating clearly under pressure isn't optional — it's core to the job.
If you're interested, please send your resume to kyle.chan@randstaddigital.com
Advantages
Nearly 30 years of stability paired with a genuine, forward-moving security practice — not just routine ticket work. Broad exposure across industries and technologies, real ownership over client security outcomes, competitive compensation with support toward certifications, and a flexible hybrid setup.
Responsibilities
Architect, configure, and maintain Microsoft 365 environments at a senior level — covering Exchange Online, Teams, SharePoint, Intune, Defender, and Purview.
Conduct in-depth security assessments, harden client tenants, evaluate compliance posture, and design Conditional Access and identity governance strategies.
Take the lead on security incidents from start to finish — triage, containment, digging through Defender/Purview logs for root cause, remediation, and clear client communication throughout, looping in legal or cyber insurance contacts when the situation calls for it.
Manage and fine-tune the broader security toolset across all client tenants — MDR/EDR alert response, running phishing simulation and security-awareness campaigns, and enforcing MFA and zero-trust access policies.
Support shared and multi-tenant environments, including delegated administration and cross-tenant collaboration setups.
Keep thorough documentation of findings, remediation steps, and ongoing security posture inside the company's PSA system, and ensure RMM configurations stay aligned with hardening standards.
Serve as the senior technical and security escalation point for the Level 1 and Level 2 support team.
Turn security frameworks like NIST CSF 2.0 and CIS Controls, plus client-specific compliance obligations, into real, auditable technical controls.
Deliver training and plain-language communication to clients across a range of industries, including reporting to executives or boards on security posture when needed.
Help shape internal standards, tenant build templates, and documentation practices company-wide.
Qualifications
Genuine comfort operating in a client-facing role — able to sit with a worried business owner mid-incident, explain what's happening without jargon, and leave them feeling more in control, not less. This is weighted just as heavily as technical ability.
5+ years of experience in a senior/Level 3 technical role; MSP background strongly preferred.
5+ years of deep, hands-on Microsoft 365 backend experience, plus the ability to guide and train end users on M365 tools.
A track record in security specifically — not just security-flavored admin work. This means real ownership of incident response, tenant hardening, or a security operations function somewhere in your background.
At least one relevant certification: Security+, SC-300 (Identity and Access Administrator), SC-400 (Information Protection Administrator), SC-200 (Security Operations Analyst), or MS-102 (M365 Administrator). Actively pursuing one also works.
Advanced knowledge of Entra ID (Azure AD), Exchange Online, Teams & Teams Phone, SharePoint Online, Intune, and both the Defender and Purview security suites.
Hands-on experience with an MDR/EDR platform, security awareness/phishing simulation tools, and MFA/zero-trust access solutions (equivalent platform experience accepted).
Working knowledge of a recognized security framework (NIST CSF or CIS Controls), with the ability to connect technical controls back to specific compliance requirements.
Solid PowerShell scripting ability for automation and tenant-wide configuration work.
Comfortable operating inside a PSA/RMM toolchain for documentation, ticketing, and monitoring.
Strong communicator — able to break down technical concepts for non-technical audiences, present findings to leadership, and manage the relationship, not just resolve the ticket.
Able to juggle multiple client environments while staying responsive and professional across all of them.
Summary
Our client is an established, Winnipeg-based IT Managed Services provider that's spent nearly three decades acting as the technology backbone for businesses across healthcare, finance, legal, and other compliance-heavy sectors. They're looking to add a Tier 3 Security & Microsoft 365 Specialist to their team — someone who treats security as their primary craft, with Microsoft 365 as the environment they operate inside, not just a system they administer.
This role isn't about ticket-driven M365 support. The ideal person can walk into an unfamiliar client tenant, diagnose what's broken or exposed, fix it properly, and then explain the "why" to a business owner who isn't technical. They're also the person clients count on when something goes seriously wrong — the calm, capable presence during an active security event.
Technical skill opens the door here, but relationship skill is what makes someone succeed long-term. This person will regularly be the one talking a stressed client through a live incident, so staying composed and communicating clearly under pressure isn't optional — it's core to the job.
If you're interested, please send your resume to kyle.chan@randstaddigital.com
Randstad Canada is committed to fostering a workforce reflective of all peoples of Canada. As a result, we are committed to developing and implementing strategies to increase the equity, diversity and inclusion within the workplace by examining our internal policies, practices, and systems throughout the entire lifecycle of our workforce, including its recruitment, retention and advancement for all employees. In addition to our deep commitment to respecting human rights, we are dedicated to positive actions to affect change to ensure everyone has full participation in the workforce free from any barriers, systemic or otherwise, especially equity-seeking groups who are usually underrepresented in Canada's workforce, including those who identify as women or non-binary/gender non-conforming; Indigenous or Aboriginal Peoples; persons with disabilities (visible or invisible) and; members of visible minorities, racialized groups and the LGBTQ2+ community.
Randstad Canada is committed to creating and maintaining an inclusive and accessible workplace for all its candidates and employees by supporting their accessibility and accommodation needs throughout the employment lifecycle. We ask that all job applications please identify any accommodation requirements by sending an email to accessibility@randstad.ca to ensure their ability to fully participate in the interview process.
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Our client is an established, Winnipeg-based IT Managed Services provider that's spent nearly three decades acting as the technology backbone for businesses across healthcare, finance, legal, and other compliance-heavy sectors. They're looking to add a Tier 3 Security & Microsoft 365 Specialist to their team — someone who treats security as their primary craft, with Microsoft 365 as the environment they operate inside, not just a system they administer.
This role isn't about ticket-driven M365 support. The ideal person can walk into an unfamiliar client tenant, diagnose what's broken or exposed, fix it properly, and then explain the "why" to a business owner who isn't technical. They're also the person clients count on when something goes seriously wrong — the calm, capable presence during an active security event.
Technical skill opens the door here, but relationship skill is what makes someone succeed long-term. This person will regularly be the one talking a stressed client through a live incident, so staying composed and communicating clearly under pressure isn't optional — it's core to the job.
If you're interested, please send your resume to kyle.chan@randstaddigital.com
...
Advantages
Nearly 30 years of stability paired with a genuine, forward-moving security practice — not just routine ticket work. Broad exposure across industries and technologies, real ownership over client security outcomes, competitive compensation with support toward certifications, and a flexible hybrid setup.
Responsibilities
Architect, configure, and maintain Microsoft 365 environments at a senior level — covering Exchange Online, Teams, SharePoint, Intune, Defender, and Purview.
Conduct in-depth security assessments, harden client tenants, evaluate compliance posture, and design Conditional Access and identity governance strategies.
Take the lead on security incidents from start to finish — triage, containment, digging through Defender/Purview logs for root cause, remediation, and clear client communication throughout, looping in legal or cyber insurance contacts when the situation calls for it.
Manage and fine-tune the broader security toolset across all client tenants — MDR/EDR alert response, running phishing simulation and security-awareness campaigns, and enforcing MFA and zero-trust access policies.
Support shared and multi-tenant environments, including delegated administration and cross-tenant collaboration setups.
Keep thorough documentation of findings, remediation steps, and ongoing security posture inside the company's PSA system, and ensure RMM configurations stay aligned with hardening standards.
Serve as the senior technical and security escalation point for the Level 1 and Level 2 support team.
Turn security frameworks like NIST CSF 2.0 and CIS Controls, plus client-specific compliance obligations, into real, auditable technical controls.
Deliver training and plain-language communication to clients across a range of industries, including reporting to executives or boards on security posture when needed.
Help shape internal standards, tenant build templates, and documentation practices company-wide.
Qualifications
Genuine comfort operating in a client-facing role — able to sit with a worried business owner mid-incident, explain what's happening without jargon, and leave them feeling more in control, not less. This is weighted just as heavily as technical ability.
5+ years of experience in a senior/Level 3 technical role; MSP background strongly preferred.
5+ years of deep, hands-on Microsoft 365 backend experience, plus the ability to guide and train end users on M365 tools.
A track record in security specifically — not just security-flavored admin work. This means real ownership of incident response, tenant hardening, or a security operations function somewhere in your background.
At least one relevant certification: Security+, SC-300 (Identity and Access Administrator), SC-400 (Information Protection Administrator), SC-200 (Security Operations Analyst), or MS-102 (M365 Administrator). Actively pursuing one also works.
Advanced knowledge of Entra ID (Azure AD), Exchange Online, Teams & Teams Phone, SharePoint Online, Intune, and both the Defender and Purview security suites.
Hands-on experience with an MDR/EDR platform, security awareness/phishing simulation tools, and MFA/zero-trust access solutions (equivalent platform experience accepted).
Working knowledge of a recognized security framework (NIST CSF or CIS Controls), with the ability to connect technical controls back to specific compliance requirements.
Solid PowerShell scripting ability for automation and tenant-wide configuration work.
Comfortable operating inside a PSA/RMM toolchain for documentation, ticketing, and monitoring.
Strong communicator — able to break down technical concepts for non-technical audiences, present findings to leadership, and manage the relationship, not just resolve the ticket.
Able to juggle multiple client environments while staying responsive and professional across all of them.
Summary
Our client is an established, Winnipeg-based IT Managed Services provider that's spent nearly three decades acting as the technology backbone for businesses across healthcare, finance, legal, and other compliance-heavy sectors. They're looking to add a Tier 3 Security & Microsoft 365 Specialist to their team — someone who treats security as their primary craft, with Microsoft 365 as the environment they operate inside, not just a system they administer.
This role isn't about ticket-driven M365 support. The ideal person can walk into an unfamiliar client tenant, diagnose what's broken or exposed, fix it properly, and then explain the "why" to a business owner who isn't technical. They're also the person clients count on when something goes seriously wrong — the calm, capable presence during an active security event.
Technical skill opens the door here, but relationship skill is what makes someone succeed long-term. This person will regularly be the one talking a stressed client through a live incident, so staying composed and communicating clearly under pressure isn't optional — it's core to the job.
If you're interested, please send your resume to kyle.chan@randstaddigital.com
Randstad Canada is committed to fostering a workforce reflective of all peoples of Canada. As a result, we are committed to developing and implementing strategies to increase the equity, diversity and inclusion within the workplace by examining our internal policies, practices, and systems throughout the entire lifecycle of our workforce, including its recruitment, retention and advancement for all employees. In addition to our deep commitment to respecting human rights, we are dedicated to positive actions to affect change to ensure everyone has full participation in the workforce free from any barriers, systemic or otherwise, especially equity-seeking groups who are usually underrepresented in Canada's workforce, including those who identify as women or non-binary/gender non-conforming; Indigenous or Aboriginal Peoples; persons with disabilities (visible or invisible) and; members of visible minorities, racialized groups and the LGBTQ2+ community.
Randstad Canada is committed to creating and maintaining an inclusive and accessible workplace for all its candidates and employees by supporting their accessibility and accommodation needs throughout the employment lifecycle. We ask that all job applications please identify any accommodation requirements by sending an email to accessibility@randstad.ca to ensure their ability to fully participate in the interview process.
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