Senior IT Support Specialist

About WeShall Investments WeShall Investments Inc. is a private equity firm supporting a growing portfolio of a dozen companies across multiple industries. Our IT team provides secure, reliable, and scalable technology services to both the firm and its portfolio companies. Role Summary The Senior IT Support Specialist provides Tier 1–2 support and light administration across our Microsoft 365 and Azure environment, with a strong focus on endpoint management (ManageEngine UEM Security), endpoint protection (CrowdStrike), identity and access (Microsoft Entra ID), remote access (Azure VPN), Mimecast email security, new-hire device provisioning, and backups. You’ll help standardize processes, improve security posture, and deliver an excellent end-user experience across the firm and portfolio. Key Responsibilities End-User Support & Service Delivery Provide Tier 1–2 support for Windows/macOS, Office/Microsoft 365 (Outlook, Teams, SharePoint, OneDrive), and common business apps. Own ticket lifecycle in the ITSM tool: triage, prioritize, resolve, and escalate according to SLAs. Create and maintain user-friendly knowledge base articles, runbooks, and quick guides. Device Lifecycle & UEM Provision, image, and configure laptops/desktops for new hires; perform replacements/refreshes and decommissions with secure data handling. Administer Zoho ManageEngine UEM Security (e.g., Endpoint Central): software deployment, patching, configuration baselines, device encryption, USB/device control, and compliance reporting. Maintain hardware inventory and asset records across the portfolio. Identity, Access & Collaboration Administer Microsoft Entra ID (Azure AD): user and group management, role assignment, MFA/Conditional Access enforcement, SSO app assignments, and periodic access reviews. Support Microsoft 365 administration: Exchange Online mailboxes, Teams/SharePoint sites, distribution lists, shared mailboxes, and OneDrive data restores. Security Operations (in coordination with IT leadership) Monitor and respond to CrowdStrike alerts; ensure agent health and policy compliance on all endpoints. Enforce security baselines (disk encryption, password/MFA, patch compliance) through UEM and Entra policies. Assist with phishing response, quarantine/release requests, and user security coaching. Networking & Remote Access Support Azure VPN clients, profiles, and connectivity troubleshooting for remote staff and portfolio users. Data Protection, Backups & DR Readiness Administer and monitor endpoint and Microsoft 365 backup jobs; perform routine test restores and document recovery procedures. Maintain backup success metrics, address failed jobs, and validate retention/restore points with stakeholders. Reporting & Analytics Build light operational dashboards in Power BI (e.g., ticket volume/SLA, patch and AV compliance, asset lifecycle, backup success rates). Provide weekly/monthly service and compliance reports to IT leadership. Portfolio Company Support Deliver remote support to portfolio-company users; coordinate with local resources or vendors for on-site needs. Support onboarding/offboarding during acquisitions/divestitures (accounts, devices, data access, and secure handovers). Process, Compliance & Vendor Coordination Follow and improve SOPs, checklists, and standards; contribute to continuous improvement. Support compliance efforts (e.g., PIPEDA, SOC 2/ISO 27001-aligned controls) through documentation, access reviews, and evidence collection. Liaise with vendors (hardware, software, MSPs) for escalations and warranty/repair. Qualifications Must-Have 3–5 years in IT support or service desk roles (multi-company or MSP experience is a plus). Hands-on experience with Microsoft 365 administration and Microsoft Entra ID (users, groups, MFA, Conditional Access). Practical knowledge of ManageEngine UEM Security (Endpoint Central or equivalent UEM) for patching, software deployment, and device compliance. Familiarity with Azure VPN (client configuration, cert/MFA troubleshooting) and basic network fundamentals. Experience preparing computers for new hires: imaging/builds, policy application, and secure decommissioning. Backup administration and performing restores for endpoints and Microsoft 365 workloads. Strong customer service ethos, clear written/verbal communication, and solid troubleshooting methodology. Ability to create clear documentation, runbooks, and user guides. Nice-to-Have Scripting/automation with PowerShell (e.g., bulk user ops, reporting, device tasks). Power BI report building (connecting to CSV/Excel/SharePoint/Graph exports). Certifications such as AZ-900, MS-900, SC-900, ManageEngine certifications Key Competencies Customer Focus • Ownership & Follow-Through • Prioritization • Documentation Discipline • Security Mindset • Analytical Thinking • Collaboration across distributed teams. Working Conditions Standard business hours with occasional after-hours maintenance/on-call rotation. Occasional travel to portfolio-company offices (as required). Must be able to lift and deploy end-user equipment safely. How to Apply Send your resume to careers@weshall.ca with the subject line “Senior IT Support Specialist – Your Name.” Include a brief note highlighting your experience with Microsoft 365, Entra ID, ManageEngine UEM, CrowdStrike, Azure VPN, and backups. Equal Opportunity Statement WeShall Investments Inc. is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We provide equal employment opportunities without regard to race, color, religion, creed, sex, sexual orientation, gender identity or expression, national origin, age, disability, genetic information, marital status, veteran status, or any other status protected by applicable law. We are committed to providing reasonable accommodations, including under the Accessibility for Ontarians with Disabilities Act (AODA), throughout the recruitment process and employment.