Technology Lead jobs

Team: Technology Operations

Reports to: Director of Technology Services

Location: Winnipeg, MB (hybrid; on-site client visits within Southern Manitoba required)

Employment type: Full-time

About Campfire

Campfire is Canada's expert in delivering Managed Services for Apple and mixed-platform environments. We are on the search for someone who is early in their IT career and is looking for a long term company where they can deliver excellence and advance their career. This position is at our Winnipeg Office, but you will join a cross Canada team of colleagues, and support clients from many provinces.

About the role

This role owns the delivery and ongoing support (as a technical escalation) of complex infrastructure for Campfire's most demanding managed service clients — including regulated environments with active external audit and compliance obligations. It is a senior, hands-on technical position: roughly a blend of project delivery (server builds, migrations, decommissions, network remediation) and L3 escalation support for issues the frontline support tiers cannot resolve.

This is not an L1/helpdesk role. The successful candidate is the person other technicians escalate to, the one who can walk into an under-documented client network and reconstruct how it works, and the who can speak confidently about complex technology issues to internal and external stakeholders. This position runs consistently high billable utilization, weighted toward Professional Services project work and escalated remote/on-site infrastructure support.

What you'll do (core responsibilities)

Infrastructure project delivery (~50% of time)

• Lead and execute server replacement, migration, and decommission projects end to end — hardware planning, build, cutover, and validation.
• Plan and run specialized maintenance and delivery windows, including after-hours work (server patching, backup reconfiguration, cutovers), with clear client communication before and after.
• Own project time and scope discipline: log time accurately against project tickets and flag when a project is trending over its budgeted hours or outside of its scope.

Network engineering & remediation

• Diagnose and resolve complex network issues
• Reconstruct and document undocumented networks and IT environments for the purposes of transitioning and delivering IT services with the larger Campfire team
• Coordinate with third-party carriers and vendors (e.g., VPN tunnel changes, ISP/telco, hardware vendors) as the technical point of contact.

L3 escalation & senior support

• Act as a senior (not primary) escalation point for frontline tiers on hardware, server, VPN, M365/Azure, and infrastructure issues.
• Provide remote-hands direction to on-site technicians and field engineers.
• Resolve recurring/systemic issues (not just tickets) — identifying root cause and implementing durable, sustainable fixes

Microsoft 365 / Azure & cloud

• Configure and support (as a senior resource) Microsoft 365 and Azure workloads
• Apply and manage endpoint/policy configuration via Group Policy and MDM/RMM tooling.

Client relationship & communication

• Serve as a trusted technical contact for client CIOs/IT managers, particularly for the assigned key account(s).
• Communicate clearly and proactively in writing (client email, Slack) about maintenance, findings, and risk.

Because this role supports regulated clients with external oversight, the successful candidate will:

• Work within audit and compliance constraints, producing documentation that stands up as an audit artifact.
• Follow client-owned and managed process such as change control, incident response, and disaster recovery
• Handle privileged credentials and access responsibly, consistent with the client's regulatory requirements.

Required qualifications

• 10+ years in an MSP, IT consultancy, or senior internal IT role, with demonstrable hands-on infrastructure project delivery
• Strong Windows Server administration: builds, migrations, decommissions, patching, backup platforms, Active Directory, DNS, DHCP, Group Policy.
• Solid networking skills: managed switching and routing, VLANs/segmentation, VPNs, troubleshooting connectivity across multi-site environments.
• Microsoft 365 and Azure administration.

Preferred / nice to have

• Experience supporting regulated clients and participating in external IT audits.
• Familiarity with the Campfire tool stack or equivalents: HaloPSA, NinjaOne
• Relevant industry certifications are an asset, for example:
  • Microsoft Azure / server: AZ-104 (Azure Administrator), AZ-800 / AZ-801 (Windows Server Hybrid Administrator).
  • Microsoft 365 / endpoint: MS-102 (Microsoft 365 Administrator), MD-102 (Endpoint Administrator).
  • Networking: CompTIA Network+, Cisco CCNA, or Fortinet NSE 4
  • Security / GRC: CompTIA Security+, AZ-500 (Azure Security Engineer Associate), or ISC2 SSCP.
  • Service management: ITIL 4 Foundation.
• Backup, DR, and business-continuity experience (BIA participation, backup scheduling design).

Success in the first 6 months looks like:

• Fully owns the assigned key account's infrastructure and is the client's trusted technical contact.
• All supported environments have current, accurate network documentation within Campfire’s knowledge management systems
• Maintains healthy billable utilization with accurate, timely time capture.

General Responsibilities

• Maintain an understanding of the Campfire support process and methodology, including desktop and server management systems, time recording and ticketing platforms and other support systems
• Achieve and maintain industry certifications relevant to your duties
• Accurately and promptly track time spent on various activities
• Ability to work independently in messy, under-documented environments and produce documentation as you go.
• Excellent written and verbal client communication; comfortable being a direct contact for senior client stakeholders.
• Valid driver's licence and willingness to travel to client sites in Southern Manitoba, including occasional after-hours/weekend maintenance work.

General Requirements

• The successful candidate must have access to a reliable vehicle and have an active Class 5 Driver’s License
• The successful candidate must satisfy the requirements of a background check
• The successful candidate must be eligible to work in Canada.

Why Work for Campfire?

We are leaders in the technology space - We expect results from our team members, but we offer good benefits, reasonable work hours, and thrive on team work. Our employees are passionate about technology and solving problems for our clients. With locations across Canada, we have plenty of opportunities to advance your IT career.

Benefits: Campfire offers traditional benefits (Health, Dental, etc) in addition to a Health Savings Account.
Schedule: Monday to Friday with participation in the on-call rotation schedule. Some ocassional ovetime may be required.

Holidays / Vacation: All Campfire employees Canada wide get 12 General Holidays in addition to 10 sicks plus your vacation time.