Sr. Desktop Support Specialist- Hybrid

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Take the next step in your journey at Inspira Financial. Guided by our mission to enable better health and greater wealth, we help businesses and individuals thrive today, tomorrow, and into retirement by strengthening and simplifying the health and wealth journey.
Serving more than 7 million clients and representing over $62 billion in assets, Inspira partners with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners to help the people they support plan, save, and invest for a brighter future. Through solutions including automatic rollover services, health savings accounts, emergency savings, and custody services, Inspira is focused on delivering better outcomes for all. Learn more at inspirafinancial.com .
Our values shape how we show up every day. We Lead with Heart by acting with compassion, empathy, and doing what's right; Cultivate Trust through integrity, transparency, and accountability; Aim Higher by never settling for what's expected and continually raising the standard; and Win Together by collaborating inclusively to achieve the best outcomes.
Our growth and culture haven't gone unnoticed -- we've been recognized on Crain's Fast 50 and Inc. 5000 for remarkable growth, and named to Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer for our workplace culture and benefits.
Don't meet every single requirement? That's okay. We know growth comes from people who are willing to learn and challenge themselves, not just check every box. If you're energized and inspired by meaningful work, continuous development, and being part of a team that turns collective effort into real impact, we want to hear from you. We look forward to receiving your application.
Remote status and role locations are subject to change, and relocation is not provided.
Employees within a 90-minute radius of our Oak Brook, IL headquarters are required to work in-office a minimum of 4 days per month from 10 am to 2 pm, with at least one day falling on a Monday or Friday. This requirement does not apply to support specialist positions.
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
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