Lead Systems Administrator

Company: The Parking Spot
Location: Schiller Park
Posted on: January 2, 2026

Job Description:

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. Salary: $100,000 What we offer: 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 Position Summary: As the Lead System Administration, 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 be at the forefront of spearheading 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. Key Responsibilities: Oversees the Systems Administration staff and activities of an organization's information systems. Assures the stability, integrity, and efficient operation of the in-house information systems that support core organizational functions. Provides support to, reviews, maintains, and optimizes all networked software and associated operating systems. Administers the planning, design, development, evaluation, testing, and integration of an organization's systems infrastructure, including the design and implementation of hardware and software. Captures, understands, translates, and documents customer requirements. Defines system and product requirements; and generates mechanical, electrical, and software performance and reliability specifications and requirements. Creates and maintains programmatic and technical documentation to ensure efficient planning and execution. Manages and documents system configurations and oversees all transitions into production. Performs troubleshooting and remediation, ensures successful project implementation, and performs post project end user support. Knowledge, Skills & Experience Required: 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 (SysAid 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 is required _____ Any disclosed pay range is based on a consideration of neutral factors and criteria such as required qualifications, experience, education, skill, training, certifications, seniority, etc. The Parking Spot reserves the right to offer the selected candidate or applicant a salary at an appropriate level to be set and determined by the employer that is commensurate with the applicant’s qualifications, experience, education, skill, training, certifications, or seniority. At The Parking Spot, we don’t just accept difference - we celebrate and seek it. We believe a diverse, inclusive, and equitable company is one where all employees, partners, and customers are welcome, supported, and valued. As a company in the travel industry, we witness the power of bringing individuals from different backgrounds and communities together. We treat all others with dignity and respect and stand firmly against racism and discrimination in any form. We intentionally develop diverse teams and relationships to ensure all voices are heard and to foster equal opportunity for all. We are committed to listening, learning, and growing because we know that our work is never done. Equal Opportunity Employer This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.

Keywords: The Parking Spot, Elmhurst , Lead Systems Administrator, IT / Software / Systems , Schiller Park, Illinois