Help Desk II

AutoSavvy; United States; On-site; USD 55,000 - 85,000; Full time

Benefits offered by this job

Medical coverage

Dental coverage

Vision coverage

HSA match

Teladoc

Pharmacy discounts

Employer paid Life Insurance

Employee Assistance Program

Pet Insurance

Gym discounts

Employee Vehicle Purchase Program

Volunteer PTO

Employer retirement matching

Extensive PTO

7 paid holidays

Job summary

AutoSavvy is seeking a Help Desk Tier II Technician to resolve escalated, higher‑complexity technology issues for employees and dealership locations. This role blends advanced desktop support with endpoint administration, identity, and store technology.

You will investigate root causes, mentor Tier 1 staff, and maintain procedures for a distributed retail environment. The ideal candidate has 2–5 years of progressive help desk or endpoint support experience, strong M365 and Entra ID skills, and a

Qualifications

• 2–5 years of progressive help desk or desktop support experience with escalated issues.
• Working knowledge of Microsoft 365 administration, Entra ID or AD, Windows endpoints, and remote support.
• Understanding of TCP/IP, DNS, DHCP, Wi‑Fi, VPN, VLAN concepts and problem isolation.
• Ability to analyze incomplete information, use logs, and document resolutions clearly.
• Experience with least‑privilege controls, change procedures, and security runbooks.

Responsibilities

• Own escalated incidents involving endpoints, authentication, and dealership apps.
• Troubleshoot using logs, telemetry, and device state to identify root causes.
• Administer functions in M365, Entra ID, Intune, Cisco Duo, and other tools.
• Document failure points and validated remediation steps.
• Support store connectivity and infrastructure at the service layer; escalate as needed.
• Mentor Tier 1 technicians and improve shared knowledge materials.
• Coordinate with vendors for third‑party issues and new site deployments.
• Handle onboarding, role changes, and access requests with least privilege.
• Travel 5%–10% for deployments and incident response across locations.

Skills

Help desk experience

Microsoft 365 administration

Entra ID / Active Directory

Windows endpoints

Remote troubleshooting

DNS / DHCP / Wi‑Fi / VPN / VLAN

Log analysis / troubleshooting

Communication / ownership

Coaching Tier 1 technicians

Retail or multi-site support

Education

Associate degree or technical diploma

Tools

PowerShell

Intune

Entra ID

Cisco Duo

Microsoft 365 admin center

Job description

AutoSavvy

At AutoSavvy, we take pride in fostering career growth and promoting from within. With 2-4 new stores opening each year, there are abundant opportunities for those motivated to learn, grow, and advance. With nearly 20 years in business, we have built a steady pipeline of high-quality, exciting vehicles, overcoming supply challenges and ensuring our team always has great options to offer.

Job Summary

The Help Desk Tier II Technician resolves escalated and higher-complexity technology issues for AutoSavvy employees and dealership locations. This role combines advanced desktop support with delegated administration of endpoints, identities, collaboration tools, security controls, and store technology. The technician is expected to investigate root causes, reduce repeat incidents, mentor Tier 1 support, and maintain the technical procedures and operational controls that keep a distributed retail environment reliable and secure.

Job Responsibilities

• Own escalated incidents and service requests involving endpoints, Microsoft 365, identity, multifactor authentication, device management, connectivity, printing, phones, and dealership applications.
• Perform structured troubleshooting using ticket history, endpoint telemetry, logs, device state, network information, vendor status, and user-reported symptoms to identify the likely root cause.
• Administer assigned functions in Microsoft 365, Entra ID, Intune, Cisco Duo, remote monitoring/support, and other approved platforms within delegated permissions.
• Diagnose device enrollment, compliance, policy, application deployment, update, and configuration issues; document the failure point and validated remediation.
• Troubleshoot store connectivity and infrastructure at the support layer, including DNS, DHCP, VLAN, Wi‑Fi, VPN, ISP, firewall, switch, and access‑point symptoms; engage the network owner or vendor when engineering‑level change is required.
• Support endpoint security alerts and suspected incidents by collecting facts, preserving evidence, isolating systems when authorized by a runbook, and escalating to the appropriate security owner.
• Complete complex onboarding, role‑change, offboarding, access, and equipment requests using approved authorization, least‑privilege, segregation‑of‑duties, and verification requirements.
• Review escalations from Tier 1 for completeness, coach technicians on troubleshooting methods, and return actionable feedback when required information is missing.
• Create and maintain knowledge articles, runbooks, checklists, technical standards, asset records, and support procedures; participate in periodic reviews so documentation remains accurate.
• Identify recurring incidents and recommend durable corrective actions, including configuration changes, user guidance, monitoring, vendor remediation, or safe automation.
• Use PowerShell or other approved tools for repeatable diagnostics and low‑risk automation; test changes, document rollback steps, and obtain approval before production use.
• Coordinate with software, telecom, internet, hardware, and dealership‑system vendors; maintain ownership of the employee experience until the issue is resolved or formally handed off.
• Support equipment deployments, store openings, refresh projects, inventory audits, and onsite incident recovery across AutoSavvy locations.
• Communicate major incidents, service risks, trends, and unresolved dependencies to IT leadership with clear business impact and recommended next steps.
• Perform other related technical‑support duties and participate in IT projects as assigned.
• 5% - 10% Business travel.

Technology Environment:

• Microsoft 365, Entra ID, Intune, Windows 10/11, Teams, Outlook, OneDrive, and SharePoint.
• GoTo Resolve or similar RMM/ticketing tools; PowerShell and remote diagnostics.
• Cisco Duo, Cisco Meraki networking, Auvik network monitoring, and GoTo voice services.
• SentinelOne or comparable endpoint security; Acronis or comparable cloud backup.
• Printers, scanners, peripherals, dealership applications, and multi‑site retail connectivity.

Required Qualifications:

• 2 to 5 years of progressive help desk, desktop support, endpoint support, or systems support experience, including responsibility for escalated issues.
• Working knowledge of Microsoft 365 administration, Entra ID or Active Directory, Windows endpoints, endpoint management, remote support, and common business applications.
• Practical understanding of TCP/IP, DNS, DHCP, Wi‑Fi, VPN, VLAN concepts, and how to isolate endpoint, network, service‑provider, and application problems.
• Demonstrated ability to analyze incomplete information, use logs and system data, test hypotheses safely, and document a technically sound resolution.
• Experience following access approvals, least‑privilege controls, change procedures, security runbooks, and evidence‑retention requirements.
• Strong written and verbal communication, service ownership, prioritization, and the ability to explain complex issues to employees and leadership.
• Ability to coach Tier 1 technicians constructively and improve shared technical documentation.

Preferred Qualifications:

• Associate degree, technical diploma, or equivalent combination of education, certifications, and hands‑on experience.
• CompTIA A+, Network+, Security+, Microsoft endpoint or Microsoft 365 certification, or another relevant industry credential.
• Hands‑on experience with Intune device enrollment and compliance, Microsoft 365 administration, Cisco Duo, Meraki, RMM platforms, endpoint security, or network‑monitoring tools.
• PowerShell experience for diagnostics, reporting, or safe task automation.
• Experience supporting retail, automotive, or another distributed multi‑location organization.
• Experience coordinating incidents with third‑party vendors and supporting new‑site deployments.
• Automotive dealership software experience preferred.

Requirements:

• Active drivers license and clean driving record
• Ability to pass a background check
• Authorization to work in the U.S

Benefits:

• Comprehensive Benefits : Medical, Dental, and Vision coverage, HSA match, TelaDoc, Pharmacy Discount Programs, and Employer paid Life Insurance
• Employee Assistance Program : Free of charge for personal uses such as support and general resources
• Additional Perks : Pet Insurance, Gym Discounts, and an Employee Vehicle Purchase Program, Volunteer PTO Program
• Retirement Savings : Employer matching contributions
• Paid Time Off : Among the best PTO policies in the industry
• Paid Holidays: 7 major holidays

Schedule:

• Full Time
• Monday to Friday
• One Saturday a month
• 9 AM to 6 PM or 7 AM to 4 PM

Physical Requirements:

• Sitting at a desk for extended periods while working on a computer.
• Occasionally lifting and moving IT equipment (e.g., servers, desktops, network devices) weighing up to 50 lbs.
• Crawling under desks or accessing server racks for cable management and hardware setup.
• Possible on-call or after-hours support for system maintenance, updates, or emergency troubleshooting.

Work Environment:

• In office andindoor work setting
• Travel to location on occasion

AutoSavvy provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.

All offers of employment at AutoSavvy are contingent upon clear results of a thorough background check and motor vehicle report (MVR). Background checks and MVRs will be conducted on all final candidates offered employment. AutoSavvy participates in E-Verify and will provide the federal government with your Form I‑9 information to confirm that you are authorized to work in the United States.