Sr. IT Technical Lead

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
Sr. IT Technical Lead will manage and optimize device ecosystem across Windows, macOS, iOS, and AndITroid. This role will lead endpoint reliability and user experience across our Windows 11 and macOS fleets. This role owns the MDM lifecycle (provisioning, policy, compliance, and deprovisioning) using Microsoft Intune and Jamf, delivers executive/white-glove support, and drives automation through scripting and API integrations. Sr. IT Technical Lead will work closely with cross-functional teams to streamline IT processes, enhance operational efficiency, and improve the overall user experience through automation. The ideal candidate will have a deep understanding of ITSM and ITIL principles, FreshService or similar platforms, and automation best practices. This role will provide technical mentorship for the team and other IT support teams. Mentoring will include training of your team members and automation workflow creations and team member assignment.
Endpoint & MDM Lifecycle Management

• Serve as an escalation point for endpoint issues (Windows/macOS/iOS/Android), collaborating with Service Desk for resolution.
• Participate and support the design, implementation, and maintenance of the MDM policies, profiles, and baselines for Windows 11 (Intune) and macOS (Jamf or similar tool), 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/AutoPilot/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, acting as an additional technical tier providing knowledge and troubleshooting assistance.

Executive / White-Glove Support

• Provide high-touch, discreet, and initiative-taking 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.

Automation, Scripting & Packaging

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

Onboarding & Offboarding

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

Preferred Qualifications
Education & Experience:

• 5-7+ years in desktop/end-user computing with Windows 11 and MacOS administration
• Bachelor's degree in computer science or related degree or related experience
• CompTIA A+, Network+, and Security+ as well as Microsoft 365 Certified: Endpoint Administrator Associate

Skills & Abilities:

• Experienced in Active Directory user administration, OS imaging processes, ticketing, SW installation, VM/VDI/Citrix, automated ticketing systems (FreshService, ServiceNow), troubleshooting in the Windows desktop environment (networking, OS, Microsoft Office suite.
• Hands-on expertise with Microsoft Intune (Windows) and Jamf Pro (macOS) for MDM lifecycle, compliance, app deployment, and scripting.
• Proven executive/white-glove support experience with excellent professionalism and discretion.
• Strong scripting ability in PowerShell (advanced), Python, or JavaScript, including REST API usage (Microsoft Graph, Jamf API, ITSM APIs).
• Experience with packaging/automation tools such as Robopack or equivalents (e.g., PDQ Deploy, Chocolatey, Winget, Jamf packages, Munki, RayPack, Ivanti).
• Deep knowledge of ITSM/ITIL processes; experience using platforms like ServiceNow, Jira Service Management, or Freshservice.
• Endpoint security skills: BitLocker/FileVault, EDR/XDR (e.g., Defender for Endpoint), vulnerability remediation, and compliance baselines.

• 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

• Strong troubleshooting across hardware, drivers, OS, networks (VPN/Wi-Fi), certificates, identity, and collaboration tools (O365, Teams/Zoom).
• Excellent communication, documentation, and stakeholder management skills.

Other Requirements:

• Infrequent travel (10%)
  • Ability to provide personal transportation from time to time.
• Ability to work overtime.
• Prolonged periods of sitting at a desk and working on a computer.

Compensation & Benefits
$88,000-$100,000 per year