Lead Systems Administrator

Join to apply for the Lead Systems Administrator role at The Parking Spot.

Since its inception, The Parking Spot has made superior airport parking experiences easy and affordable by focusing on hospitality. Now with more than 25 years in business, The Parking Spot has cemented itself as the leading near‑airport parking company with 40+ locations at 28 airports, over 2,000 employees nationwide and 2 incredibly strong brands – The Parking Spot and Park ‘N Fly by The Parking Spot.

What makes working at The Parking Spot so special? We have created a culture of support, fun, and camaraderie that allows us to be the most innovative company in the parking industry. As a nationwide business with a small‑business feel, there are endless opportunities within The Parking Spot to grow your career. Come join us and see how we leverage people and technology to deliver a superior product, outshine our competition, and find creative and innovative solutions to everyday problems.

• Participation in and financial benefit from our shared employee ownership program
• Hybrid work experience in downtown Chicago
• Career development and growth opportunities
• Ability to gain exposure to all areas of the business
• Great benefits including Medical, Vision, Dental and a 401k plan
• Annual discretionary bonus program
• Team oriented, fun and friendly work environment
• Immediate opportunity to make a large impact

As the Lead System Administrator, you’re responsible for setting up, deploying, documenting, and maintaining end‑user technology for the IT Infrastructure Team. This includes Windows workstations, iOS devices, Windows application servers, camera/DVR systems, among other operating and office hardware. The role also entails establishing, installing, and making The Parking Spot’s proprietary revenue and operations technologies function.

As our Lead Systems Administrator, you will spearhead efforts to identify and apply new technical solutions, conceptualize new tools to optimize system performance, and streamline processes to be efficient and well‑documented. Attention to detail, adherence to documented procedures, and problem‑solving for challenging technical issues are a requirement. You will maintain systems, processes, and inventory management while communicating project status and technical solutions clearly and professionally.

• Oversee the Systems Administration staff and activities of an organization’s information systems.
• Assure the stability, integrity, and efficient operation of the in‑house information systems that support core organizational functions.
• Provide support to, review, maintain, and optimize all networked software and associated operating systems.
• Administer the planning, design, development, evaluation, testing, and integration of an organization’s systems infrastructure, including the design and implementation of hardware and software.
• Capture, understand, translate, and document customer requirements.
• Define system and product requirements; generate mechanical, electrical, and software performance and reliability specifications and requirements.
• Create and maintain programmatic and technical documentation to ensure efficient planning and execution.
• Manage and document system configurations and oversee all transitions into production.
• Perform troubleshooting and remediation, ensure successful project implementation, and provide post‑project end‑user support.

• Strong attention to detail and excellent customer service skills.
• Excellent interpersonal, problem analysis, and resolution skills.
• Excellent oral and written communication abilities.
• Experience managing a helpdesk ticketing system (Sys Aid preferred).
• Experience with Intune.
• Experience with Active Directory administration.
• Experience with VoIP administration.
• Experience supporting an environment with remote assistance.
• Experience with low voltage cabling, relays, and other gate hardware systems a plus.
• Bachelor’s degree in a computer science–related field preferred; 3+ years of work experience may be considered.
• 20‑30% travel required.

Any disclosed pay range is based on a…