Lead IT Support Specialist
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Summary
An experienced IT professional who owns the day-to-day support queue across nine automotive dealerships (500+ endpoints), resolving hardware, software, VoIP, and Microsoft 365 issues onsite and remotely. Core stack: Windows 11, Microsoft 365, Entra ID/Azure AD, Exchange Online, Teams, and VoIP phones.
Lead IT Support Specialist
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Location
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Multiple Automotive Dealerships along the Central Coast
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Position Type
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Full-Time
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Reports To
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IT Manager (no direct reports)
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Schedule
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Monday through Friday, daytime hours, with occasional after-hours support as needed.
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Position Summary
This role is responsible for owning the day-to-day IT support queue, resolving the majority of end-user technical issues, and providing both remote and onsite support across multiple dealership locations. The ideal candidate has strong troubleshooting skills, Microsoft 365 experience, exceptional customer service skills, and an experience-first mindset.
This is not an entry-level Help Desk position, nor is it an engineering role. We are looking for an experienced IT professional who can independently resolve most support requests while knowing when and how to escalate more complex issues to senior IT staff.
With more than 500 endpoints across nine dealerships, this position plays a critical role in keeping our users productive and our technology systems running efficiently.
What You'll Do
- Manage and prioritize incoming support tickets across multiple dealership locations.
- Own the ticket board: set priorities, assign or reassign tickets, request more detail on unclear requests, and close unresponsive tickets after follow-up.
- Serve as the primary point of contact for end-user technical support.
- Troubleshoot hardware, software, mobile device, connectivity, SaaS technician tool, and VoIP phone issues.
- Provide onsite and remote support to dealership personnel.
- Provide clear instructions and hands-on guidance to end users, helping them understand company technology and work more efficiently.
- Support Windows desktops, laptops, mobile devices, and peripheral equipment.
- Administer and support Microsoft 365 services, including:
- User account management
- License assignment
- Password resets
- Exchange Online
- Microsoft Teams
- Distribution groups
- Entra
- Support Microsoft Entra ID (Azure AD) user administration.
- Assist with endpoint deployment and management.
- Perform employee onboarding and offboarding tasks.
- Configure and deploy computers, peripherals, and mobile devices.
- Maintain accurate documentation of technical issues and resolutions.
- Identify recurring issues and recommend process improvements.
- Coordinate and communicate effectively with users, vendors, and IT team members.
- Escalate infrastructure, networking, cybersecurity, and application issues when appropriate.
- Protect customer financial and personal data in line with the FTC Safeguards Rule, including MFA, access controls, and phishing reporting.
- Travel between dealership locations as needed to provide onsite support.
What Your Day-to-Day Will Look Like
- You will touch a wide variety of systems, software, and devices.
- Pull camera footage as requested and authorized.
- Onboard and offboard users.
- Address phone call routing issues.
- Install and replace workstation components and peripherals.
- Strive for an empty ticket board.
- Assist users with email setup and password changes.
- Modify user permissions and grant access to company resources.
Required Qualifications
- 3+ years of professional IT support experience.
- Exceptional customer service and communication skills, with an experience-first mindset.
- Strong troubleshooting skills across hardware, software, and Microsoft environments.
- Experience supporting Microsoft 365.
- Experience with:
- Windows 11
- Microsoft Entra ID (Azure AD) or Active Directory
- Microsoft Teams
- Exchange Online
- Basic networking knowledge, including:
- TCP/IP
- DNS
- DHCP
- Wi-Fi troubleshooting
- Experience working in a ticketing system.
- Experience supporting VoIP phone systems, including call routing and handset troubleshooting.
- Experience supporting and troubleshooting networked printers and multifunction devices.
- Experience instructing or training users on technology, with the ability to explain technical concepts in plain language.
- Ability to manage multiple priorities and work independently.
- Valid driver's license and willingness to travel between locations.
Preferred Qualifications
- Experience supporting multiple locations or retail-style environments.
- Experience supporting automotive dealership locations.
- Experience with Microsoft Intune.
- MSP (Managed Services Provider) experience.
- Experience with endpoint management and device lifecycle management.
- Microsoft certifications or equivalent technical training.
What Success Looks Like
In this role, you will:
- Resolve the majority of incoming support requests independently, with a high percentage closed without escalation.
- Serve as the trusted technology resource for dealership employees and managers.
- Maintain a healthy, organized, and responsive support queue.
- Keep ticket aging and backlog low, with few or no tickets left open beyond an agreed number of days.
- Earn strong user satisfaction on closed tickets.
- Regularly add and update knowledge base articles for recurring issues.
- Reduce escalations by effectively troubleshooting and resolving issues at the first point of contact.
- Help identify opportunities for process improvement and automation.
- Allow senior IT staff to focus on infrastructure, security, projects, and strategic initiatives.
Why Join Us?
You'll be part of a collaborative IT team that values ownership, accountability, customer service, and continuous improvement. This role offers the opportunity to make a significant impact across multiple dealership locations while working with modern Microsoft technologies and helping drive operational excellence throughout the organization.