Sr. Desktop Support Specialist

Join Us!
Take the next step in your journey at Inspira Financial. You will help businesses and individuals thrive today, tomorrow, and into retirement. Become part of a company that is people centric and client obsessed in every interaction; a community of forward-thinking individuals focused on driving results to deliver our mission with an unwavering commitment to integrity. Join us as we strengthen and simplify the health and wealth journey -- relentlessly pursuing better outcomes for all. We believe in finding the best talent! While some roles are based at one of our office locations, remote roles can sit in any of the following states: AL, AZ, FL, GA, IA, IL, IN, MI, MN, MO, NC, NE, PA, SC, TN, TX, UT, VA and WV. Remote status and role locations are subject to change. Relocation is not provided.
Employees within a 90-minute radius of our Oak Brook, IL headquarters are required to adhere to the company in-office work guidelines of 4 days per month minimum from 10 am to 2 pm (1 of the 4 days must be a Monday or Friday).
This requirement does not apply to support specialist positions.
Don't meet every single requirement? Here at Inspira Financial, we believe there is no "perfect" candidate and want to encourage applying even if all the requirements listed aren't met. Our goal is to build an authentic workplace by valuing diversity in our candidates. We work to ensure that our team reflects the diversity of the businesses and clients we serve. We are always looking to expand our growing team with dynamic and enthusiastic individuals. If you enjoy a collaborative, fun environment that champions career development, Inspira Financial is the place for you! We look forward to receiving your application! Check out this Inspira Financial video to learn more about our company!
Inspira Financial provides health, wealth, retirement, and benefits solutions that strengthen and simplify the health and wealth journey. With more than 7 million clients, representing over $62 billion in assets, Inspira works with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners -- helping the people they care about plan, save, and invest for a brighter future. Inspira relentlessly pursues better outcomes for all with our automatic rollover services, health savings accounts, emergency savings funds, custody services, and more. Learn more at inspirafinancial.com .
We have been recognized for our remarkable growth on lists such as Crain's Fast 50 and Inc. 5000, and for our outstanding workplace culture and benefits with Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer awards.
Job Summary & Responsibilities
The Sr. Desktop Support Specialist will report to the Desktop Support Manager in the Technology Department. This role is responsible for providing employees located in our corporate office, as well as remote locations, with Level 1 and 2 support for the desktop environment including deployment of desktops and laptops and when applicable physical server/network equipment installation, configuration, application installation, troubleshooting, incident and request handling. Although rare, this position is expected to be responsive after hours to both end user issues and emergency text alerts for critical servers and applications.
Duties & Responsibilities:

• Diagnose, research and troubleshoot computer system issues, including operating systems, hardware and software, networking, VPN, connectivity, anti-virus and other network devices/peripherals, both remotely and on-site
• Serve as a main point of contact for handling escalated issues and resolving more complex technical issues
• Research complex problems and work with vendors on support issues including coordination of hardware warranty repair
• Assist with management of Exchange and Active Directory environments
• Assist with management of mobile devices via Airwatch or Intune
• Assist with management of various corporate services and applications
• Own and drive implementation of new software, upgrades of existing software and procedural documentation and other projects
• Utilize strong understanding and skills in Incident and Request Management for tracking and reporting requirements.
• Provide on-call emergency services after business hours, holidays and weekends as required
• Other duties as assigned

Preferred Qualifications
Education & Experience:

• 3-5 years of experience in Help Desk, System Admin, or Desktop Support role
• Bachelor's Degree in Computer Science or related degree or related experience required
• CompTIA A+, or MCSA Certifications preferred

Skills & Abilities:

• Experienced in Active Directory user administration, OS imaging processes, ticketing, SW installation, VM/VDI/Citrix, SCCM, automated ticketing systems, troubleshooting in the Windows desktop environment (networking, OS, Microsoft Office suite, PC hardware), network and local printer installation
• Intermediate level understanding of SCCM client troubleshooting
• Knowledge of TCP/IP, Windows Security (Share and NTFS permissions)
• Extensive knowledge Windows OS and related configuration
• Knowledge of Servers, Switches, Routers, and Data Center related HW
• Experience in handling escalated issues, resolving more complex technical issues
• Experience with VOIP/Telephony systems
• File server maintenance and management of shares and quotas
• Familiar with remote user support (VPN/RSA/Citrix/VDI)
• A self-starter able to work with minimal direct supervision
• Must have excellent written and verbal communication skills
• Ability to present ideas and solutions in user-friendly language
• Must be able to analyze issues and have excellent troubleshooting skills
• Must be comfortable working in a fast-moving environment and willing to step up and take responsibility for their deliverables
• Ability to prioritize tasks and manage overall workload
• Ability to communicate status of tasks (progress and milestones)
• Ability to research complex problems
• Experience working with tickets and internal customers directly
• Highly self-motivated and directed
• Experience in a high availability environment preferred

Other Requirements:

• Infrequent travel (10%)
  • Ability to provide personal transportation from time to time
• Occasionally lifts up to 25 pounds
• Prolonged periods of sitting at a desk and working on a computer

Compensation & Benefits
$28.00/hr-$33.00/hr