Sr. Desktop Support Specialist

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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 people‑centric and client‑obsessed community focused on driving results and delivering 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 be located 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.

The Sr. Desktop Support Specialist will report to the Desktop Support Manager in the Technology Department. This role is responsible for providing Level 1 and 2 support for the desktop environment, including deployment of desktops and laptops, physical server/network equipment installation, configuration, application installation, troubleshooting, incident and request handling. The position is expected to be responsive after hours to both end‑user issues and emergency text alerts for critical servers and applications.

• 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, 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.

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

• 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 of Windows OS and related configuration.
• Knowledge of Servers, Switches, Routers, and Data Center related hardware.
• 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.
• Excellent written and verbal communication skills.
• Ability to present ideas and solutions in user‑friendly language.
• Excellent troubleshooting skills and analytical ability.
• Comfortable working in a fast‑moving environment and willing to step up and take responsibility for deliverables.
• Ability to prioritize tasks and manage overall workload.
• Abili…