Onsite IT Director

Onsite IT Director - _Lake Barrington, IL_Are you ready to apply Make sure you understand all the responsibilities and tasks associated with this role before proceeding._*$80,000-$110,000 annually *__(based on experience)__*Full benefits package*__: Health, dental, vision, FSA/HSA, 401(k) with match, life insurance, paid time off, bonus incentives, and on-site gym access._*Who We Are:*Union One is a rapidly expanding benefits management firm dedicated to delivering essential income protection solutions to Union Members. Our mission is to bring peace of mind to our customers by offering smart, supportive, and secure group benefit solutions. Guided by our core values "” integrity, service, insight, and advocacy "” we're proud to support our Union Members through life's unexpected moments.*Role Overview*The Onsite IT Director is responsible for the overall reliability, security, and scalability of Union One's technology environment. This role owns the design, operation, and continuous improvement of all IT systems, including infrastructure, networking, security, and end-user services.You will lead day-to-day IT operations while also setting technical direction, prioritizing initiatives, and ensuring systems align with business needs. This is a hands-on leadership role "” you are expected to both guide strategy and directly engage in complex technical work when needed.*Key Responsibilities**Infrastructure & Architecture Ownership** Own the design and operation of: Virtualization platform (Hyper-V), Remote Desktop Services (RDS) infrastructure and On-prem and cloud-integrated systems* Define and maintain standards for system configuration, performance, and availability* Plan and execute infrastructure upgrades, migrations, and lifecycle management*Networking & Connectivity** Oversee network architecture, including switching, VLANs, Wi-Fi, and VPN* Manage firewall and network security posture (Meraki or similar platforms)* Ensure reliable connectivity between on-prem, remote users, and cloud services*Security & Risk Management** Own identity and access management strategy (AD, Microsoft 365, MFA)* Define and enforce security policies and best practices* Lead vulnerability remediation, patching strategy, and incident response* Support compliance initiatives (SOC 2 or similar frameworks)*Microsoft 365 & Business Systems** Oversee Microsoft 365 ecosystem (Exchange, Teams, SharePoint, OneDrive)* Ensure reliability and performance of line-of-business applications* Manage integrations between systems and ensure data accessibility*IT Operations & Support Leadership** Oversee IT support function (Tier I / Tier II)* Establish processes for ticketing, escalation, and incident management* Ensure timely resolution of issues and high end-user satisfaction* Develop and maintain IT documentation and SOPs*Data & Automation Enablement** Support data operations by ensuring reliable access to systems and datasets* Identify opportunities for automation and operational efficiency* Oversee storage, file systems, and data handling practices*Vendor & Project Management** Manage relationships with vendors, service providers, and consultants* Evaluate and select new technologies aligned with business needs* Lead IT projects from planning through execution with minimal disruption*Monitoring, Backup & Disaster Recovery** Ensure monitoring is in place for all critical systems* Own backup strategy and regularly validate restore processes* Maintain disaster recovery plans and test periodically*Required Onsite IT Director Qualifications** 7+ years of experience in IT infrastructure, systems administration, or related roles* 2+ years of experience in a senior or lead IT role* Strong hands-on experience with: Windows Server (AD, GPO, DNS/DHCP), Microsoft 365 administration, Virtualization (Hyper-V preferred), and Networking fundamentals (VLANs, VPNs, firewalls)* Proven ability to troubleshoot complex, cross-system issues* Experience leading projects and making technical decisions independently* Strong documentation, communication, and organizational skills* Ability to work onsite daily in Lake Barrington, IL*Strong Candidates Will Have** Experience with: Cisco Meraki networking stack, VPN technologies (AnyConnect or similar), Linux server environments (Ubuntu or similar), Scripting/automation (PowerShell, Python)* Experience managing or mentoring IT staff xijylhu * Familiarity with monitoring and observability tools (Grafana, Zabbix)* Experience supporting environments with RDS or similar multi-user systems* Exposure to compliance and security frameworks*What Success Looks Like** IT systems are stable, secure, and well-documented* Issues are resolved quickly with clear root cause and prevention* Infrastructure scales cleanly with business growth* IT operations run predictably without constant escalation*Equal Employment Opportunity*Union One is an Equal Employment Opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, pregnancy, national origin, ancestry, age, disability, veteran status, marital status, order of protection status, genetic information, arrest record, conviction record, or any other status protected by applicable law.*Accommodations*Union One provides reasonable accommodations to qualified individuals with disabilities in accordance with applicable law.Pay: $80,000.00 - $110,000.00 per yearBenefits:* 401(k) matching* Dental insurance* Flexible spending account* Health insurance* Health savings account* Life insurance* Paid time off* Vision insuranceExperience:* IT infrastructure: 7 years (Required)* Senior IT Role: 2 years (Required)Ability to Commute:* Lake Barrington, IL 60010 (Required)Work Location: In person

Created: 2026-04-03