Tier 2 IT Support & Cloud Operations Specialist (Remote)

Company: Jorie AI
Location: Oak Brook
Posted on: April 1, 2026

Job Description:

About Jorie AI Jorie AI occupies a uniquely interconnected position at the center of the healthcare industry. As an inseparable part of today's healthcare billing ecosystem, we use leading-edge, AI-infused Robotic Process Automation (RPA) to transform end-to-end Revenue Cycle Management (RCM) and provide premier financial and practice management services. Our Work Environment Remote-First: 100% remote opportunities within the USA. Career Growth: Significant potential for advancement. Work-Life Balance: Flexible environment promoting personal well-being. Culture: Collaborative and friendly company atmosphere. Benefits & Perks Financial: 401(k) matching up to 4%. Health: Comprehensive Medical, Dental, and Vision insurance. Security: Employer-paid Life insurance ($25,000) plus Long/Short Term Disability. Time Off: 2 weeks PTO and 10.5 paid holidays. Job Overview We are hiring a high-performing Tier 2 technician who operates well beyond entry-level support. This role supports our Azure and Microsoft 365 environment, virtual infrastructure (VMs and VDI), endpoint management, and identity services. You should already be a strong systems-minded administrator. This role is for someone who understands how things work under the hood — and is actively pushing into security, not just talking about it. We operate in a regulated environment supporting healthcare-related functions. Security, compliance, and accountability are part of daily operations, not afterthoughts. Responsibilities Act as an escalation point beyond Tier 1 and own complex incidents end-to-end Troubleshoot advanced Windows 11, mobile device, and virtual machine performance issues Support Azure infrastructure, including VMs, Development, and virtual desktop environments Administer Microsoft 365 (Exchange Online, Teams, SharePoint, licensing) Manage Entra ID (user lifecycle, group management, MFA, access control issues) Deploy and enforce Intune device policies and compliance standards Diagnose and remediate endpoint security posture issues Own patch validation, vulnerability remediation, and system hardening Document thoroughly and follow structured operational practices Maintain strong alignment with HIPAA/HITRUST security controls Required Experience 4–6 years of progressive IT support/systems administration experience Proven Tier 2 capability with independent problem-solving Hands-on Azure experience (VMs, RBAC, identity concepts) Strong Microsoft 365 administration background Experience with Intune-managed endpoints Experience supporting VDI (Azure Virtual Desktop preferred) Demonstrated root-cause troubleshooting ability

Keywords: Jorie AI, Chicago , Tier 2 IT Support & Cloud Operations Specialist (Remote), IT / Software / Systems , Oak Brook, Illinois