Help Desk Manager

White Owl Family Office Group; Markham; On-site; CAD 85,000 - 110,000; Full time

Job summary

White Owl Group is building an in‑house Private MSP to serve portfolio companies. The Service Desk Manager will design and run the service desk, set SLAs, and lead a small team across multiple entities in Markham, Ontario.

You will coordinate escalations with infrastructure teams, manage IT operations, and report on performance while working with senior leadership. Candidate must have MSP experience and strong ITSM skills.

Qualifications

• Minimum 5 years of IT support experience.
• Minimum 2 years in a supervisory or MSP service delivery role.
• Experience supporting multiple clients or portfolio companies.
• Familiarity with ITSM frameworks and ticketing platforms.

Responsibilities

• Lead the service desk function for multiple portfolio companies.
• Define SLAs and manage escalation workflows.
• Build and mentor a growing team of service desk technicians.
• Maintain and optimize ITSM platform configurations and runbooks.
• Report on service desk metrics and drive continuous improvements.

Skills

IT support

Team leadership

MS 365

Azure AD/Entra

AD & RBAC

Networking basics

ITSM

MSP exposure

Education

Bachelor's degree in IT/CS

Tools

ServiceNow

Jira Service Management

Zendesk

HaloPSA

Job description

Reports To: Director of IT Operations, White Owl Group

Employment Type: Full-Time, Permanent

Location: Markham, Ontario (with travel to portfolio company sites as required)

Position Summary

White Owl Group is a family office with a growing portfolio of operating businesses across multiple sectors. As the family office builds out its internal technology function, we are establishing a Private MSP — a centralized, in-house IT shared services team that delivers enterprise-grade support across all portfolio companies.

The Service Desk Manager will lead this function from the ground up. This is a high-impact role for someone who thrives in a multi-entity, entrepreneurial environment: you will design and operate the service desk, set standards, manage a small but growing team of technicians, and serve as the primary IT point of contact across White Owl’s portfolio businesses. You will work closely with leadership at both the family office and individual portfolio companies to ensure technology enables — rather than hinders — business performance.

The Service Desk Manager will own the full lifecycle of IT support across the portfolio — from first contact through to resolution — including coordinating escalations to ensure nothing falls through the cracks. Reporting to the Head of IT Operations, this role sits at the centre of White Owl’s technology function and is critical to how the family office delivers value to its businesses.

Essential Duties and Responsibilities

Multi-Entity Service Delivery

• Serve as the primary IT support contact for all White Owl Group portfolio companies, acting as an embedded MSP for each business.
• Triage, prioritize, and resolve support requests spanning diverse environments, industries, and user bases across the portfolio.
• Establish and enforce service level agreements (SLAs) with each portfolio company, tailored to their size, criticality, and needs.
• Manage ticket queues and escalation workflows, owning the handoff process to infrastructure and escalation teams — defining criteria, tracking resolution progress, and holding SLA accountability end-to-end even when tickets are in another team’s queue.
• Monitor and respond to support channels including email, phone, and ITSM ticketing system to ensure prompt, professional responses.
• Develop and maintain a shared knowledge base, support runbooks, and per-company environment documentation.
• Build, hire, onboard, and manage a team of service desk technicians as the Private MSP scales with the portfolio.
• Create work schedules, on-call rotations, and coverage models that align with the operating hours and risk profiles of portfolio companies.
• Provide coaching, mentoring, and technical direction to develop team capabilities and career growth.
• Conduct regular team meetings, performance reviews, and skills assessments.
• Identify and address skills gaps through training, certifications, or targeted hiring.

Technical Support & Infrastructure

• Provide hands‑on support for hardware, software, and network issues across Windows environments.
• Troubleshoot escalated issues involving Microsoft 365, Azure AD/Entra ID, business applications, and endpoint devices.
• Support device deployments, refresh cycles, and configuration management across portfolio companies.
• Assist with mobile device management (MDM), endpoint protection, and identity/access management.
• Coordinate with the infrastructure and escalation teams on complex or systemic issues, as well as external vendors, ISPs, and managed security providers on behalf of portfolio businesses.
• Participate in an on‑call rotation to cover after‑hours emergencies across the portfolio.
• Track, analyze, and report on service desk metrics (ticket volume, resolution time, SLA adherence, first‑contact resolution, CSAT) for the family office and individual portfolio companies.
• Prepare regular performance reports for White Owl Group leadership and portfolio company stakeholders.
• Identify recurring issues and drive root cause resolution in collaboration with technical and business teams.
• Recommend and implement process improvements that reduce ticket volume and improve user self‑sufficiency.
• Maintain and optimise the ITSM platform configuration, including automation rules, workflows, and reporting dashboards.

The Service Desk Manager does not manage the infrastructure team, but holds coordination authority over the escalation process across all teams. This includes:

• Define, document, and maintain escalation criteria and handoff procedures between the service desk and infrastructure and escalation teams (network, systems, and ERP).
• Assign and route escalated tickets to the appropriate team, providing clear context, priority, and business impact information.
• Track the status of all escalated tickets, proactively following up to ensure progress and prevent stalls.
• Retain SLA ownership for escalated issues — even when resolution sits with another team, the SDM is accountable for keeping the portfolio company informed and the ticket moving.
• Facilitate communication between end users and technical resolvers, translating business impact into technical priority and vice versa.
• Identify patterns in escalation volume and work collaboratively with infrastructure team leads and the Head of IT Operations to address root causes and reduce repeat escalations.
• Participate in cross-functional IT meetings and contribute to joint planning for major changes, incidents, or portfolio company onboardings.

Stakeholder Engagement & Communication

• Build trusted relationships with portfolio company leadership, operations teams, and end users across diverse business environments.
• Communicate planned maintenance, system outages, and service updates clearly and proactively to all affected stakeholders.
• Develop and deliver end‑user training on common applications, security practices, and self‑service tools.
• Act as a technology advisor to portfolio company leadership on IT operational matters.
• Handle escalated complaints with professionalism, ensuring timely resolution and a positive outcome.

Minimum Qualifications

Experience & Background

• Minimum 5 years of experience in IT technical support or service desk roles.
• Minimum 2 years in a supervisory, team lead, or MSP service delivery capacity.
• Experience supporting multiple clients, companies, or business units simultaneously (MSP, shared services, or multi‑site experience strongly preferred).
• Demonstrated track record improving service delivery metrics and customer satisfaction.
• Experience with IT service management (ITSM) frameworks and ticketing platforms.

Technical Knowledge & Skills

• Strong knowledge of Windows, desktop/laptop hardware, and standard troubleshooting methodologies.
• Proficiency with Microsoft 365 suite (Exchange Online, Teams, SharePoint, OneDrive) and Azure AD / Entra ID.
• Experience with Active Directory, user account lifecycle management, and role-based access control.
• Working knowledge of networking fundamentals: TCP/IP, DNS, DHCP, VLANs, VPN.
• Familiarity with remote support tooling, MDM solutions (Intune or equivalent), and endpoint protection platforms.
• Experience with ITSM ticketing systems (ServiceNow, Jira Service Management, Zendesk, HaloPSA, or similar).
• Understanding of ITIL service management principles and best practices.

Core Competencies

• Exceptional client service orientation — able to navigate diverse stakeholder personalities and organizational cultures across the portfolio.
• Strong leadership and team development instincts, with the ability to attract and retain good technical talent.
• Effective problem‑solver who can balance urgent reactive support with longer‑term service improvement initiatives.
• Calm, professional, and decisive under pressure — able to manage competing priorities across multiple organisations.
• Strong communicator who can translate technical concepts for non‑technical business leaders.
• Entrepreneurial mindset: comfortable building structure and process in a growing, dynamic environment.
• High degree of personal accountability and follow‑through.

Education & Certifications

Associate’s or Bachelor’s degree in Information Technology, Computer Science, or a related field preferred; equivalent combination of education and demonstrated experience will be considered.

Preferred certifications:

• CompTIA A+, Network+, or Security+
• Microsoft Certified: Modern Desktop Administrator or Microsoft 365 Fundamentals / Associate
• ITIL Foundation or higher

Working Conditions

• Primary work location at White Owl Group’s Markham, Ontario office.
• Regular travel to portfolio company sites across the Greater Toronto Area and surrounding regions.
• Occasional evening or weekend work for scheduled maintenance or urgent incidents.
• Participation in an on‑call rotation for after‑hours emergency support.
• Ability to lift and transport computer equipment up to 50 lbs.
• Valid driver’s licence and access to reliable transportation required.

This job description is not intended to be exhaustive. Duties, responsibilities, and activities may evolve as White Owl Group’s portfolio and technology needs grow. New responsibilities may be assigned at any time with or without notice.

This position requires satisfactory completion of a background check as a condition of employment.