Salary Range: $65,000.00 To $75,000.00 Annually The Team at Lark

Whether it is innovative hospitals, health districts, affordable homes, community recreation, brain health, first-responder support, training and education, or the most advanced medical and clinical care Lark Group’s purpose is always about people.

The Lark Group of Companies focuses on

BOLDLY ELEVATING PEOPLE by providing clear goals and deliverables aligned with our corporate strategic plan and inspiring our employees to embrace our core values. At the Lark Group, our employees are A-players who live, breathe and exude our DNA our purpose and our values.

Our values guide how we work every day:

Drive, Authentic, Respect, Elevate, Safety, and Bold . They are more than words they shape our decisions, our relationships, and the way we support each other, our partners, and the communities we serve.

As a future employee of the Lark Group, you are someone who is challenged and inspired to work with the best people in your industry. When you read our purpose and core values, you feel connected to them, inspired by them and excited to work with others who live by them.

Position Summary

We’re looking for an IT Support Specialist to be the frontline technology resource for the Lark Group companies. This is a hands-on, fully onsite role for someone who fixes things properly, communicates well with people who aren’t technical, and takes ownership of a request until it’s actually resolved.

You’ll own the daily front line end to end helpdesk requests, Microsoft 365, onboarding and offboarding, device deployment, and the documentation that keeps it all repeatable working across our construction, development, hospitality, and health technology companies.

You’ll work alongside our internal IT lead, and by owning day-to-day support you create the room for them to focus on cybersecurity, infrastructure, vendor strategy, Microsoft 365 administration, AI adoption, and long-term technology planning. If you like solving problems, being visible to the people you help, and leaving things better documented than you found them, you’ll fit well here.

What You’ll Be Doing

You’ll own the front line of IT support, including:

End-User Support

Providing Tier 1 and junior Tier 2 technical support to employees across Lark Group companies

Troubleshooting Windows computers, laptops, monitors, docking stations, printers, scanners, mobile devices, and peripherals

Resolving common issues in Outlook, Teams, OneDrive, SharePoint, Word, Excel, and other Microsoft 365 applications

Handling password resets, MFA enrollment, account access, profile issues, and connectivity problems





Receiving, prioritizing, documenting, and following through on support requests using the established helpdesk process

Microsoft 365 & Identity

Creating, updating, and disabling user accounts following approved onboarding and offboarding processes

Supporting Microsoft 365 licensing, mailbox access, shared mailboxes, distribution groups, Teams memberships, and calendar permissions

Supporting OneDrive synchronization and SharePoint access requests

Assisting with Entra ID user administration, MFA, and sign-in troubleshooting within delegated permissions

Escalating advanced identity, security, mail-flow, compliance, or tenant-level issues to the internal IT lead

Device Deployment & Asset Management

Preparing, configuring, and deploying laptops, desktops, mobile devices, monitors, docks, and accessories

Installing approved applications and confirming devices meet Lark configuration and security standards

Coordinating equipment replacements, repairs, returns, and secure disposal

Maintaining accurate hardware, software, assignment, warranty, and location records

Completing routine inventory checks across supported offices and sites

Business Application Support

Providing first-line assistance for Adobe, Bluebeam, Procore, Autodesk, Acumatica, Salesforce, Monday.com , and other approved company applications

Handling basic installation, licensing, access, and profile troubleshooting, and escalating application-specific problems when required

Infrastructure & Office Technology

Assisting with Wi-Fi, wired network, VPN, ISP, meeting-room, audiovisual, printer, and office technology troubleshooting

Performing basic network checks involving connectivity, DHCP, DNS, cabling, access points, switches, and firewalls under direction

Coordinating with telecom, internet, managed-service, and equipment vendors as assigned

Cybersecurity & Compliance

Helping employees adopt MFA and other security controls

Recognizing and promptly escalating suspected phishing, malware, compromised accounts, data exposure, or unusual sign-in activity

Helping maintain device, access, and software standards, and reinforcing approved IT practices with users

Maintaining technical procedures, onboarding checklists, asset records,



and knowledge-base articles

Documenting recurring issues, root causes, resolutions, and escalation paths

Identifying opportunities to standardize common support tasks and improve the employee support experience

Safety & Values

Working safely across offices, sites, and server and equipment spaces

Working in a way that reflects Lark’s values: Drive, Authentic, Respect, Elevate, Safety, and Bold

Who You Are

You have 2–3 years of progressive IT support, service desk, desktop support, or systems support experience

You’re a strong troubleshooter across Windows 10/11 and the Microsoft 365 applications

You’ve done real Microsoft 365 user administration and worked in Entra ID / Azure AD

You know your way around Outlook, Exchange Online, Teams, SharePoint, OneDrive, and MFA

You have sound networking fundamentals — TCP/IP, DNS, DHCP, Wi-Fi, VPN, and basic switching

You’re patient and transparent with people who aren’t technical, and you fix the person’s day as well as the machine

You juggle multiple requests without dropping any, document carefully, and close the loop

You take ownership and push work forward without waiting to be told

You recognize risk and elevate at the right moment — not too early, not too late

You value clarity, honesty, and doing things properly — even when it’s hard

You hold a valid driver’s licence and can travel between Lark locations when required

Nice to have: CompTIA A+, Microsoft 365 Fundamentals, Microsoft Endpoint Administrator, or comparable training

Nice to have: endpoint management, cybersecurity tooling, or device deployment experience

Nice to have: experience in construction, real estate, property management, healthcare technology, or other multi-company environments

Why This Role Is Different

You’ll support the people building projects that genuinely matter to communities

You’ll be trusted to run the front line, not micromanaged through a ticket queue

One environment, many companies — construction, development, hospitality, and health technology, so no two days look the same

You’ll work directly with the internal IT lead and have real line of sight into infrastructure, security, and AI adoption

You’ll have real influence over how support gets delivered here, not a process handed to you

You’ll be part of a team that expects a lot — and supports you to deliver it

What We Offer

We take care of our people — genuinely and holistically. This role comes with a competitive compensation package and benefits that reflect the value of the work and the impact of the role.

📌 IT Specialist (Winnipeg)
🏢 LARK GROUP
📍 Winnipeg