Systems Administrator

About Diamond Parking
Founded in 1922, Diamond Parking is one of the nation's largest privately held parking operators. Our IT team keeps the company's 2,000+ locations running smoothly supporting point-of-sale systems, mobile apps, and the corporate offices that serve our customers every day. Join us and help power the technology behind convenient parking solutions across North America.

Role Overview

As a Systems Administrator, you will maintain and improve Diamond Parking's core Windows infrastructure-on-premises and in Microsoft 365. You'll handle day-to-day support tickets, perform routine server maintenance, and contribute to small infrastructure projects, all while delivering outstanding customer service to end users. This role reports to the Director of IT and works closely with a Systems Engineer and the service desk team. This is an in-person position.

Key Responsibilities

Required Qualifications

• 3+ years administering Windows Server (2012 R2 or newer) and Microsoft 365.
• Hands-on troubleshooting with Active Directory, Group Policy, DNS, Azure AD, VPN, and basic firewall rules (Fortinet a plus).
• Proficiency with PowerShell for routine tasks and automation.
• Familiarity with backup solutions, patch management, and endpoint protection.
• Strong written and verbal communication skills; able to explain technical issues to non-technical staff.
• Organized, detail-oriented, and able to juggle multiple support requests in a fast-paced setting.
• Willingness to work standard office hours (Mon-Fri) plus occasional evenings/weekends for maintenance.
• Willingness and ability to travel up to 15%

Preferred Extras (nice to have, not required)

• CompTIA Security+, Network+, Microsoft Certified: Windows Server Hybrid Administrator, or similar certs.
• Experience with Intune, Azure Virtual Desktop, or basic scripting in Python/Bash.
• Exposure to PCI-DSS or other compliance frameworks.

Benefits & Perks

Diamond Parking offers a comprehensive benefits package for full-time employees, including:

• Medical, Dental, and Vision plans
• Health Savings and Flexible Spending Accounts
• Company-paid Life and AD&D insurance
• Short- and Long-Term Disability coverage
• Employee Assistance Program (EAP)
• Tuition Reimbursement
• 8 paid holidays, paid vacation, and sick leave per applicable laws

Salary: We maintain broad salary ranges for our roles in order to account for variations in experience, training skills, geographic location, and market conditions, as well as to reflect our differing products and lines of business. The pay range referenced is as of the time of the job posting.

Benefits:

Full-Time Employees

For full-time employees, we offer a comprehensive benefits package (subject to elections and eligibility) that includes Medical, Dental, Vision, Health Savings Accounts and/or Flex Spending Accounts, Employer Provided Life and AD&D Insurance, Voluntary Life Insurance and AD&D, Employer Provided Long-Term Disability Insurance, Voluntary Short-Term Disability Insurance, Personal Accident Plan, Employee Assistance Program, Non-Qualified Deferred Compensation Plan, and Tuition Reimbursement.

We offer 8 paid holidays per calendar year, paid sick leave, and paid vacation once eligibility requirements are met.

Part-Time Employees:

The company offers paid sick time to all employees once eligibility requirements are met.

We are committed to a diverse and inclusive workplace. We are an equal opportunity employer and do not discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status.