Company Overview:
Lightspeed is the leading provider of cloud-based software for dealerships, serving the Powersport, Marine, RV, Trailer, and Golf Car industries adding hundreds of dealerships to the Lightspeed community each year.
Lightspeed’s Dealer Management Solution (DMS) enables dealerships to optimize their end-to-end business operations, including Sales, Parts, Service, Rentals, Payments, Accounting, and Customer Relationship Management (CRM). When implemented into their daily operations, Lightspeed helps dealers increase their profitability by selling more units, service, and parts, all while creating a more streamlined experience for customers.
Lightspeed is the most complete and integrated DMS in the industry with over 500 integrations with Original Equipment Manufacturers (OEMs), aftermarket parts and accessory distributors and dozens of other software tools that a dealership may use to run their business. Uniquely designed by dealers for dealers, and refined over the past 4 decades, Lightspeed empowers over 4,500+ dealers across North America with the tools and technology they need to manage their dealerships.
Position Summary
As a Supervisor, IT Help Desk, you will lead and mentor the IT Help Desk team, serving as the escalation point for complex technical issues and ensuring the delivery of high-quality support services to internal employees. You will be responsible for team performance, staffing, process improvement, and cross-functional collaboration with Systems Administrators and IT leadership. This role is ideal for an experienced IT professional who is passionate about people management, operational excellence, and creating a service-first support culture.
What You’ll Do
Team Leadership & Management
- Supervise, coach, and mentor a team of Tier I and II IT Support Technicians, fostering a collaborative and high-performance culture.
- Conduct regular one-on-ones, performance reviews, and development conversations with team members.
- Manage scheduling and staffing to ensure adequate coverage and support for business operations.
- Onboard and train new help desk technicians, ensuring alignment with established procedures and quality standards.
- Identify skills gaps and coordinate training opportunities to support team growth and career development.
Escalation & Technical Support
- Serve as the primary escalation point for complex or high-priority issues that exceed Tier I and II scope.
- Collaborate with Systems Administrators and IT leadership to resolve escalated tickets in a timely manner.
- Maintain hands-on technical proficiency in areas including Microsoft 365, Entra ID (Azure AD), endpoint management, and network troubleshooting.
- Step in to provide direct end-user support during peak demand or staffing gaps as needed.
Ticket & Queue Management
- Monitor the ticketing queue to ensure tickets are correctly prioritized, assigned, and resolved within SLA targets.
- Analyze ticket trends and recurring issues to identify opportunities for proactive resolution or process improvement.
- Generate and review weekly/monthly reports on team performance, ticket volume, SLA compliance, and customer satisfaction.
- Define and enforce ticketing standards, ensuring complete and accurate documentation of all support interactions.
Process Improvement & Documentation
- Develop and maintain IT procedures, runbooks, and knowledge base articles to improve team efficiency and consistency.
- Identify opportunities to automate or streamline repetitive support tasks.
- Establish and refine escalation paths, workflows, and service delivery standards.
- Ensure the team knowledge base is current, accurate, and consistently used across the team.
Cross-Functional Collaboration
- Partner with Systems Administrators and IT management on projects, infrastructure changes, and planned maintenance.
- Communicate upcoming changes, outages, or IT initiatives to end users with appropriate advance notice.
- Represent the help desk in IT team meetings and contribute to strategic planning discussions.
- Gather and relay user feedback to drive continuous improvement in IT services.
Equipment & Asset Management
- Oversee the team’s management of hardware inventory, equipment deployments, and onboarding/offboarding processes.
- Ensure accurate tracking of IT assets and enforce asset management policies and procedures.
- Coordinate equipment procurement requests and work with vendors or procurement teams as needed.
What You Should Have
Qualifications
- 4+ years of experience in IT support or help desk roles, with at least 1–2 years in a lead or supervisory capacity.
- Solid working knowledge of Windows operating systems, Microsoft 365 (Outlook, Teams, SharePoint, OneDrive), and Entra ID (Azure AD).
- Demonstrated experience managing or mentoring a team in a technical support environment.
- Strong understanding of ITSM principles, including ticketing, SLA management, and escalation workflows.
- Excellent interpersonal and communication skills – able to engage effectively with both technical staff and non-technical end users.
- Ability to analyze support data and metrics to drive decision-making and continuous improvement.
- Strong organizational skills with the ability to manage multiple priorities in a fast-paced environment.
- Customer-focused mindset with a commitment to service quality and user satisfaction.
Preferred Qualifications
- CompTIA A+ or Network+ certification
- Microsoft 365 Certified: Administrator Expert or similar Microsoft certification
- ITIL Foundation certification
- Experience with enterprise ticketing platforms (ServiceNow, Jira Service Desk, Zendesk, etc.)
- Familiarity with endpoint management tools (Microsoft Intune, SCCM, or similar)
- Experience developing or delivering IT training for end users or junior staff
- Associate’s or Bachelor’s degree in Information Technology, Computer Science, or a related field
Inclusion and Diversity at Lightspeed:
At Lightspeed, we celebrate the uniqueness of every individual and encourage diverse perspectives. We believe that inclusion drives innovation and fosters meaningful connections. We are committed to building an environment where everyone feels valued and empowered to make an impact.
Equal Employment Opportunity Statement:
Lightspeed is an Equal Opportunity Employer and is dedicated to building a diverse and inclusive workforce. All qualified applicants will be considered for employment without regard to race, color, creed, ancestry, national origin, gender, sexual orientation, gender identity, gender expression, marital status, religion, age, disability, veteran status, or any other protected category.
Important Note:
Applicants must be authorized to work in the U.S.
Ready to apply?
Take the next step in your career—apply today and join a team where your skills will make an impact!
