IT Support Technician - Tier II

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:

What you'll do:

As an IT Support Technician - Tier II, you will serve as an escalation point for complex technical issues that go beyond initial Tier I troubleshooting. You will provide advanced support for hardware, software, network, and infrastructure issues, while also mentoring Tier I technicians and contributing to the overall maturity of the IT support function. This role is well suited to an experienced technician ready to deepen their technical expertise and take on greater ownership of systems and processes.

Advanced End-User Support

• Serve as the escalation point for Tier I technicians on complex or unresolved hardware, software, and connectivity issues.
• Diagnose and resolve Tier 2 technical issues, including recurring problems that require root-cause analysis.
• Handle escalated or sensitive support requests with professionalism, ensuring minimal disruption to business operations.

Microsoft 365 Administration

• Administer Microsoft 365 services including Exchange Online, Teams, SharePoint, and OneDrive at an intermediate/administrative level.
• Configure and troubleshoot mailbox permissions, distribution lists, shared mailboxes, and mail flow rules.
• Support conditional access policies, multi-factor authentication (MFA), and license assignment/management.

Device, Endpoint & Network Support

• Troubleshoot advanced Windows/Linux/Mac desktop, laptop, and server issues, including performance and configuration problems.
• Manage endpoint deployment, imaging, and configuration using MDM/endpoint management tools (e.g., Intune).
• Diagnose and resolve network connectivity issues including VPN, Wi-Fi, DNS, and DHCP problems, escalating to Network/Systems Administrators when needed.
• Support printer, AV, and conference room technology, including root-cause troubleshooting for recurring hardware issues.

Identity & Account Management

• Administer user accounts, groups, and permissions in Entra ID (Azure AD) and Active Directory, including more complex access scenarios.
• Support identity-related projects such as group policy updates, conditional access changes, and access reviews.
• Audit account and permission changes for accuracy and compliance with security policies.

Ticket Management & Escalation

• Manage a queue of escalated tickets, ensuring timely resolution and clear documentation.
• Review and guide Tier I ticket handling, providing feedback and coaching as needed.
• Escalate complex infrastructure or systems issues to Systems Administrators or IT Management with clear context and troubleshooting history.

Documentation & Knowledge Base

• Create, review, and maintain advanced support documentation and knowledge base articles.
• Standardize troubleshooting procedures and best practices across the IT support team.
• Identify documentation gaps and partner with Tier I staff to keep resources current.

Mentorship & Team Support

• Mentor and train Tier I Support Technicians, helping to build their technical and customer service skills.
• Act as a technical resource and point of escalation for the Tier I team.
• Contribute to onboarding and training materials for new IT support staff.

Projects & Continuous Improvement

• Participate in IT projects such as system migrations, software rollouts, and infrastructure upgrades.
• Identify opportunities to automate or streamline recurring support tasks.
• Assist with equipment lifecycle management, including onboarding/offboarding, inventory, and hardware deployment at scale.

Learning & Development

• Stay current with company systems, tools, security practices, and emerging technologies.
• Pursue relevant certifications and training to grow technical expertise.
• Provide guidance and mentorship to junior IT staff as part of ongoing professional development.

What you should have:

Qualifications:

• 3-5 years of experience in help desk, technical support, or IT support role, including experience handling escalated issues.
• Solid understanding of Windows operating systems, Windows Server fundamentals, and common business applications.
• Intermediate to advanced experience with Microsoft 365 administration (Exchange Online, Teams, SharePoint, OneDrive).
• Working knowledge of networking fundamentals (TCP/IP, DNS, DHCP, VPN, Wi-Fi troubleshooting).
• Experience administering Entra ID (Azure AD) and/or Active Directory, including user, group, and access management.
• Strong customer service skills with the ability to communicate technical concepts clearly to non-technical users.
• Demonstrated ability to mentor or guide junior team members.
• Excellent organizational skills with the ability to manage multiple escalations and priorities simultaneously.
• Strong problem-solving skills with a focus on root-cause analysis rather than temporary fixes.

Preferred Qualifications:

• CompTIA Network+ or Security+ certification.
• Microsoft 365 Certified: Modern Desktop Administrator Associate (or equivalent).
• ITIL Foundation certification.
• Experience with endpoint management/MDM tools (e.g., Microsoft Intune).
• Basic scripting experience (e.g., PowerShell) for automating routine tasks.
• Experience with ticketing systems (ServiceNow, Jira Service Desk, Zendesk, etc.) in an escalation or lead capacity.
• Familiarity with basic server administration and virtualization concepts.
• Associate's or Bachelor's degree in Information Technology or 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!