Desktop Support Technician; Automotive

Career Opportunities with Holler Classic Corporate Office

Current job opportunities are posted here as they become available.

Subscribe to our RSS feeds to receive instant updates as new positions become available.

Holler-Classic Family of Dealerships, an Automotive News Top 150 dealership group with 12 dealerships serving the Central Florida market, has been proudly family‑owned since 1938. Our Buy Smart – Be Happy® brand promises include Our Best Price First, Pure and Simple® and Commission‑Free Sales. The perfect candidate will be based in our Group’s home office in Winter Park (conveniently located off Lee Rd.

exit on I‑4).

As a Desktop Support Technician, you will have the opportunity to make a positive impact on our business and the lives of team members and customers every day. We are looking for a driven, dedicated individual who is excited by the opportunity to join a successful, growing team and continue to drive home the culture of success that has been built over nearly nine decades.

Duties and Responsibilities include, but are not limited to, the following:

• Provide technical support for desktops, laptops, and mobile devices (primarily Windows environment, with some macOS and Android endpoints)
• Set up and troubleshoot hardware: monitors, docking stations, printers, and peripherals
• Install, configure, and maintain software applications and operating systems
• Support business specific software applications, such as:
  • DMS – Auto/Mate, Reynolds & Reynolds
  • F&I Menu – Darwin
  • Service Lane Technology – xTime, my Kaarma, Tru Video
  • Quickbooks
  • Marketron
• Manage user accounts and permissions in Active Directory/Azure AD
• Use remote support tools to assist users at Company’s 16+ locations
• Document issues and resolutions in a ticketing system
• Assist with device imaging, deployment, and inventory management
• Support employee onboarding and offboarding (equipment setup, access provisioning)
• Enforce security best practices (MFA, secure password policies, device encryption)
• Additional duties, as assigned by management

• Minimum of two years of prior desktop support experience
• Strong communication skills with the ability to support users from entry‑level to C‑suite (via phone, email/chat, or in person)
• Ability to lift up to 50 lbs.
• Willingness to serve in on‑call rotation (typically one weekend per month)
• 401(k) & 401(k) Matching
• Employee Assistance Program
• Health Insurance
• Vison Insurance
• Life Insurance
• Flexible Spending Account
• Paid Time Off After 6 months
• Referral Program
• Associate Discount Program

• None

• Full‑Time

• Ability to work a flexible schedule

• $19-$23/hr

Holler and Classic Family Collection of Dealerships is proud to be an equal opportunity workplace. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, Veteran status or other legally protected characteristics. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. We participate in the E‑Verify program.

Upon an applicant's request, Holler and Classic Family Collection of Dealerships will consider reasonable accommodation to complete the application process.

https://(Use the "Apply for this Job" box below)./