Job Description

POSITION: DIRECTOR OF IT/POS

ABOUT THE COMPANY

Tom’s Watch Bar defines the ultimate sports watching entertainment experience.

Promising “All the Sports, All the Time”, Tom’s Watch Bar’s highly curated sports programming covers all sports, from collegiate to professional to international, big events and prize fights, even emerging obscure, and outrageous sports. Tom’s Watch Bar’s central oversized “stadium” screen, surrounded by hundreds of screens provides 360-degree viewing, making every seat at Tom’s the best seat in the house.

Tom’s Watch Bar is a fast-growing and exciting new restaurant and bar concept. They are looking for an executive to lead their accounting and control functions as they begin a significant ramp up of the brand and new locations.

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POSITION OVERVIEW:

The Director of IT/POS is responsible for the day-to-day operational management, maintenance, and reliability of Tom’s Watch Bar’s IT, POS, and network environments across all restaurants, the Support Center, and SIF Group offices. This role ensures all systems function effectively, issues are resolved quickly, vendors are managed tightly, and the business has dependable technology to operate smoothly.

This position requires a hands-on leader who is comfortable working independently, troubleshooting directly, and managing multiple external vendors while supporting a fast-growing restaurant organization.

ROLES & RESPONSIBILITIES

Core Technical Operations

• Oversee daily performance, uptime, and functionality of all restaurant IT systems.
• Manage and support POS (Toast/Brink), including menu updates, configuration changes, troubleshooting, and integrations.
• Own network health across all locations, including switches, access points, firewalls, and connectivity.
• Monitor and manage infrastructure performance, proactively resolving issues before they disrupt operations.
• Oversee desktop and device management, including computers, tablets, printers, and peripherals.
• Maintain and enforce network, communication, and platform security standards.
• Manage and coordinate PCI compliance, ensuring all restaurants meet requirements and documentation is maintained.

Vendor & Partner Management

• Source, evaluate, onboard, and oversee third-party vendors supporting:
• POS (Toast/Brink)
• Network equipment and services
• Infrastructure projects
• Managed Wi-Fi partners
• Security monitoring tools
• Low-voltage contractors
• Ensure all vendors meet expectations for response times, SLAs, security, performance, and deliverables.
• Review invoices, control costs, and evaluate vendor performance regularly.

Support & Field Operations

• Manage the restaurant Help Desk , ensuring timely resolution of tickets, escalations, and trends.
• Analyze Help Desk data to provide recommendations for reducing repeat issues.
• Serve as the escalation point for complex restaurant IT, POS, or network issues.
• Support operators by being accessible, responsive, and proactive about upcoming needs or system impacts.

New Restaurant Openings

• Lead all IT components of new restaurant openings, including:
• Network installation and testing
• POS installation, programming, and validation
• KDS configuration
• Low-voltage coordination
• Wi-Fi vendor setup
• Hardware deployment and QA
• Ensure all systems are fully functional before soft opening and opening day.

Systems Maintenance & Execution

• Perform routine system checks, updates, and patching across all technologies.
• Maintain accurate documentation of networks, device inventories, configurations, and restaurant layouts.
• Manage user access, permissions, and security controls across all platforms.
• Support Restaurant365 and Back-of-House integrations as needed.

Project Execution

• Manage IT projects such as hardware upgrades, new tool rollouts, security enhancements, and software deployments.
• Keep projects on schedule and within scope.
• Communicate updates clearly to operators and Support Center teams

Data, Reporting & Monitoring

• Track system performance, device uptime, incident reports, and technology KPIs.
• Provide actionable, operational recommendations based on Help Desk and system data.
• Maintain dashboards or reporting tools that help operators understand restaurant performance issues related to IT.

QUALIFICATIONS

• Willing and able to work daily from the Support Center and answer field needs in real-time.
• Hands-on operational experience supporting POS, networking, and restaurant tech environments.
• Strong understanding of:
• POS systems (Toast/Brink preferred)
• Network hardware & configuration
• Wi-Fi management platforms
• Security tools & best practices
• PCI compliance requirements
• Experience sourcing, managing, and evaluating external vendors.
• Organized, detail-oriented, and able to juggle multiple concurrent activities.
• Strong troubleshooting and diagnostic skills.
• Excellent communication skills and the ability to explain technical concepts clearly.
• Experience with Restaurant365 or similar restaurant back-office systems preferred.
• Project management experience (PMP a plus).
• Comfortable in a fast-paced, growing environment with shifting priorities.
• Commitment to supporting our culture, acting with ownership, and being highly service-oriented.

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