Are you a senior MSP engineer who can deliver large infrastructure projects hands-on and act as the technical advisor a client relies on?

We’re hiring a

Senior Systems Engineer

to join a managed services and cloud hosting provider working across Microsoft 365, Azure, and virtualized infrastructure. The role leads hands-on implementations and migrations for the company’s clients and serves as the lead technical contact for one key enterprise account, guiding its project planning and technical decisions.

Who You Are

A senior engineer accustomed to the demands of a managed services setting, able to reprioritize effectively as client needs change

A professional who takes ownership of outcomes and exercises sound technical judgement within acceptable risk, with minimal oversight

Solution-oriented under pressure, consistently presenting viable alternatives when an approach is not feasible

A trusted advisor who communicates risks, gaps, and constraints to clients clearly and candidly

Composed and credible in client settings, whether in virtual meetings, in person, or during a critical incident

Someone who demonstrates accountability, respect and integrity in every interaction and holds their work to a high standard

Work Type

Location:

Toronto, ON (Hybrid, 3 days per week)

Vacancy Type:

This role reflects an existing vacancy

What You’ll Do

Deliver hands-on implementation and migration projects for the company’s clients, which make up roughly 90% of the role

Serve as the lead technical contact for one key enterprise account, taking part in its regular planning meetings on upcoming initiatives

Help the client evaluate proposed projects,



identifying risks, dependencies, and considerations before plans are finalized

Contribute to project scoping and solution design with the company’s architects, bringing a detailed understanding of the client’s environment

Implement infrastructure refreshes and modernization projects, including new server hardware and virtualized environments across multiple sites

Work across Microsoft 365, Azure, and cloud hosting environments supporting database-driven applications on SQL and Linux

Coordinate the technical response for the key account during serious incidents, drawing on knowledge of its environment and priorities

What We’re Looking For

5+ years

of hands-on experience in an MSP environment, delivering implementations and infrastructure projects

Solid experience with Microsoft 365 and Azure in a managed services setting

Experience with server infrastructure and virtualization platforms such as Hyper-V or VMware

Experience supporting database-driven environments, including SQL databases and Linux servers

A track record of planning and executing migrations and infrastructure refreshes for business clients

Experience acting as a technical point of contact for clients, advising on project plans and risks





The ability to work independently and make sound technical decisions within agreed boundaries

Strong communication skills with client IT teams, internal architects and leadership, in person and virtually

Nice to have:

Experience as a Technical Account Manager or in a client-facing technical lead role

Experience with HPE VM

Exposure to SAP Business One environments

What Makes This Role Exciting

Strategic Client Ownership:

Serve as the trusted technical advisor to one of the company’s most significant clients, with direct influence on how its largest initiatives are planned and delivered

Large-Scale Infrastructure Work:

Lead projects of greater scale and complexity than a typical MSP engagement, with major initiatives already planned over the next two years

Decision-Making Autonomy:

Exercise genuine technical judgement within defined risk boundaries, without approval required at every step

Team-Backed Accountability:

Own the client relationship with the full Professional Services team supporting the account’s delivery

Base Salary:

$110,000 – $130,000

Paid Time Off:

Competitive vacation and personal days to maintain a healthy work-life balance

Health Benefits:

Medical benefits to support your overall well-being

We’re proud to support diversity and inclusion. Need accommodation during the hiring process? Just let us know — we’re here to support you!

AI Use Disclosure:

STACK IT uses AI-enhanced tools to support initial candidate screening and interview note analysis. All assessments and hiring decisions remain human-led.

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📌 Senior Systems Engineer (Winnipeg)
🏢 STACK IT Recruitment
📍 Winnipeg