Sr. IT Technical Lead

Overview

Join Inspira Financial to help businesses and individuals thrive today, tomorrow, and into retirement. Be part of a people-centric, client-obsessed team focused on driving results with integrity and delivering better outcomes in the health and wealth journey.

We believe in finding the best talent. Remote roles may be based in 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 Oak Brook, IL headquarters are required to adhere to in-office guidelines (4 days per month, 10 am–2 pm;

1 of the 4 days must be Monday or Friday). This requirement does not apply to support specialist positions.

Inspira Financial provides health, wealth, retirement, and benefits solutions to strengthen and simplify the health and wealth journey. Learn more at  We are recognized for growth and workplace culture with industry awards.

Sr. IT Technical Lead will manage and optimize the device ecosystem across Windows, macOS, iOS, and Android. This role leads endpoint reliability and user experience across Windows 11 and macOS fleets, owns the MDM lifecycle (provisioning, policy, compliance, deprovisioning) using Microsoft Intune and Jamf, delivers executive/white-glove support, and drives automation through scripting and API integrations. The role works with cross-functional teams to streamline IT processes, improve operational efficiency, and enhance user experience through automation.

The ideal candidate has a deep understanding of ITSM/ITIL, Fresh Service or similar platforms, and automation best practices. The role provides technical mentorship for the team and other IT support teams, including training and automation workflow creation.

• Serve as an escalation point for endpoint issues (Windows/macOS/iOS/Android), collaborating with Service Desk for resolution.
• Design, implement, and maintain MDM policies, profiles, and baselines for Windows 11 (Intune) and macOS (Jamf or similar), covering security, compliance, encryption, patching, app deployment, and configurations.
• Own the device lifecycle: procurement intake, enrollment, configuration, periodic health checks, OS/app updates, offboarding/retirement (wipe, reassignment, data retention), and auditing.
• Develop and maintain Zero-Touch/Auto Pilot/ABM provisioning workflows.
• Monitor and remediate endpoint vulnerabilities (OS/app patching, misconfigurations, EDR alerts, device posture).
• Improve device performance, stability, and user experience through telemetry, analytics, and feedback.
• Mentor and support the Deskside and Helpdesk teams as an additional technical resource for knowledge and troubleshooting.

• Provide high-touch, discreet support for C-suite and senior leaders, including conference room/AV readiness and rapid incident resolution.
• Create personalized runbooks and VIP device standards to minimize downtime and ensure exceptional experience.

• Drive automation program implementation and toolsets to reduce impact on end users.
• Build and maintain automation for deployment, configuration drift correction, compliance remediation, and self-service tasks using Microsoft Power Automate and integrations across Azure AD/M365/Fresh service/Intune/Jamf.
• Develop automation with Power Shell, Power Automate, or similar tools (REST/SOAP API integrations with Intune, Microsoft Graph, Jamf, and ITSM platforms).
• Package and deploy applications/updates using packaging tools; improve silent installs, versioning, rollback, and dependency management.
• Maintain ITSM processes aligned to ITIL (Incident, Service Request, CMDB, Knowledge).

• Integrate HRIS triggers (e.g., new hire/term updates) with ADP/Fresh service/Intune/Jamf and M365.

Education & Experience:

• 5–7+ years in desktop/end-user computing with Windows 11 and macOS administration
• Bachelor’s degree in computer science or related field or equivalent experience
• CompTIA A+, Network+, and Security+ and Microsoft 365…