IT Technical Lead at The Bartolotta Restaurants

Milwaukee, Wisconsin, United States -

Full Time

Start Date

Immediate

Expiry Date

25 Feb, 26

Salary

0.0

Posted On

27 Nov, 25

Experience

2 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Technical Support, Cybersecurity, Systems Administration, Network Management, Microsoft 365, Azure AD, Intune, POS Systems, Project Management, Team Leadership, Documentation, Compliance, Risk Analysis, Vendor Management, Operational Support, Troubleshooting

Industry

Restaurants

Description

Description The IT Technical Lead is responsible for the security, stability, enhancements, and daily operation of all technology systems across the restaurant group. This role oversees IT infrastructure, cybersecurity, systems administration, and multi-site operational support. The IT Technical Lead ensures that all technology supports efficient service, safe transactions, and reliable business operations. This position is also responsible for supporting and contributing to technology planning efforts, improving standards, and maturing the IT environment. The role includes one direct report (Desktop Technician) and regular collaboration with departments and leadership within Bartolottas. The IT Technical Lead reports to the CEO. Requirements Technical Support Serve as the primary Tier 3 escalation point for networking, systems, security, server, telecommunication, and POS issues across all locations. Deploy, configure, and optimize Fortinet firewalls, switches, access points, telecommunication devices, VPNs, and segmented networks—ensuring PCI DSS-aligned controls. Administer Microsoft 365, Entra ID/Azure AD, Intune, and associated identity, access, and security configurations. Collaborate with application support to troubleshoot Toast POS, Paylocity, PeopleVine, OpenTable, and restaurant-specific integration issues. Manage device configurations using Intune, Mosyle, and other MDM platforms. Perform on-site support involving network drops, cabling, hardware installation, repairs, and restaurant-environment troubleshooting. Partner with vendors if required to remediate issues and problems. IT Operations & Daily Support Oversee daily IT operations and the timely resolution of tickets for users across multiple restaurant locations. Manage endpoints, POS hardware, printers, A/V systems, network equipment, and guest-facing systems. Ensure that accounts, permissions, and access are managed according to company policy and security standards. Maintain consistent patching, updates, backups, and preventive maintenance for all systems. Monitor ticket patterns to identify recurring issues, root causes, and opportunities for improvement. Partner with IT vendors on projects and incident remediations if required. Team Oversight Supervise and mentor the Desktop Technician, providing direction, feedback, technical support, and setting workload and expectations. Lead IT onboarding and offboarding, including provisioning, configuration, access setup, and training. Promote a culture of communication, accountability, documentation, and continuous improvement. Project Execution & Implementation Plan and lead IT projects such as network upgrades, POS rollouts, hardware refreshes, cloud migrations, and new-location openings. Develop timelines, task lists, testing plans, and change-management processes. Partner with Operations, HR, Finance, Marketing, and venue managers to ensure technology solutions support business needs. Produce clear documentation, diagrams, SOPs, and post-implementation reviews. Security, Compliance & PCI DSS Serve as the primary lead for PCI DSS compliance activities, audits, SAQs, vendor attestations, and annual reviews. Maintain required security controls including MFA, encryption, endpoint protection, and least-privilege access. Conduct Targeted Risk Analyses (TRA) and maintain PCI DSS v4.0 compliance records. Review vulnerabilities, logs, alerts, and security findings; coordinate remediation activities. System Administration & Infrastructure Management Administer and maintain network infrastructure including firewalls, switches, Wi-Fi systems, VPNs, and segmentation. Support cloud and on-prem systems to ensure performance, availability, and security. Monitor system health, alerts, and capacity; tune performance and troubleshoot issues. Maintain asset inventory, licensing, and hardware life cycles. Documentation, SOPs & Continuity Maintain IT documentation, SOPs, knowledge bases, and disaster-recovery materials within SharePoint. Ensure changes, deployments, and troubleshooting steps are documented consistently. Support business continuity planning and review recovery procedures regularly. Operational Improvements & Enablement Identify opportunities to improve workflows, automate processes, and enhance technology usage across departments. Evaluate new hardware and software tools for suitability and assist in deployment and training. Build strong partnerships with IT vendors. QUALIFICATION REQUIREMENTS: Highly organized and self-directed with strong follow-through. Ability to build relationships across all levels of the organization. Exceptional interpersonal, written, and verbal communication skills. Strong project management and prioritization skills. Ability to operate effectively in a fast-paced, multi-site environment. Analytical mindset with strong problem-solving and strategic thinking abilities. Demonstrated leadership skills. EDUCATION AND/OR EXPERIENCE REQUIREMENTS: Associate or Bachelor’s degree in Information Technology, Computer Science, or related field preferred; equivalent experience considered. Minimum three years of hands-on IT technical support or systems administration experience, ideally in a multi-site environment. Strong technical knowledge of Microsoft 365, cybersecurity, Azure AD/Entra ID, Intune, and Windows client management. Experience administering multi-site network environments. Understanding of PCI DSS and IT governance best practices. Experience supervising or mentoring IT team members. Valid driver’s license and ability to travel as needed. PHYSICAL REQUIREMENTS: Ability to sit, stand, and work at a computer for extended periods. Ability to lift up to 40 lbs of hardware equipment. Ability to kneel, crouch, or work in tight or low-clearance spaces (counters, closets, back-office areas). Ability to climb a step stool or small ladder to access cabling or mounted equipment. Adequate vision to read wiring, screens, and documentation. Ability to travel frequently between locations, occasionally during evenings or weekends for urgent issues. Ability to work in varying restaurant environments (kitchens, coolers, front-of-house spaces).

Responsibilities

The IT Technical Lead is responsible for the security, stability, enhancements, and daily operation of all technology systems across the restaurant group. This role oversees IT infrastructure, cybersecurity, systems administration, and multi-site operational support.