REGIONAL FIELD IT DIRECTOR (REMOTE-EAST)

Job Summary:

The Regional Field IT Director provides technical leadership and operational oversight for venue technology systems across Levy properties within their assigned geographic region.

Supporting approximately 75–85 venues of varying scale and complexity across multiple states, this role ensures that technology platforms critical to guest transactions and venue operations are reliable, well-governed, and operationally optimized.

Working in close partnership with the Levy Digital Strategy team, the Regional Field IT Director serves as the regional technical authority and solution advisor, helping translate technology strategy into scalable and supportable implementations across venues.

If Digital Strategy leaders define what technology should be deployed and why, the Regional Field IT Director determines how those technologies should be implemented, supported, and operated at scale within live event environments.

This role leads a regional team of Area IT Managers, Field Engineers, and venue technology associates, and partners closely with Levy operational leadership to ensure consistent support practices, strong vendor accountability, and event-ready technology environments.

The Regional Field IT Director also plays an important role in evolving the field technology organization into a data-informed, operationally disciplined, and innovation-ready technology function.

Responsibilities:

Technical Advisory & Solution Architecture

• Serve as the regional subject matter expert for venue technology platforms and infrastructure.
• Partner with Levy Digital Strategy to evaluate new technologies and provide input on technical feasibility, deployment considerations, infrastructure requirements, and operational support needs.
• Translate strategic technology initiatives into scalable and operationally sound implementations across venues.
• Provide technical guidance across the hospitality technology ecosystem including POS platforms, payment systems, self-checkout and frictionless technologies, mobile ordering platforms, kiosks, networking infrastructure, and digital guest experience technologies.

Regional Technology Operations & Event Readiness

• Ensure stable operation of technology systems across approximately 75–80 venues within the region.
• Establish consistent operational support practices across venues and regional IT teams.
• Serve as the regional escalation point for major technology incidents impacting venue operations.
• Drive improvements in technology reliability and operational performance, including reductions in system outages, event-day failures, and offline payment transactions.
• Establish event readiness standards and ensure systems are validated prior to scheduled events.
• Provide on-site leadership during major national events or high-profile venue operations when required.

Regional Team Leadership

• Lead and develop a regional team of Area IT Managers, Field Engineers, and venue technology associates.
• Promote a culture of accountability, collaboration, and technical excellence within the field IT organization.
• Ensure teams maintain strong technical expertise across all deployed technology platforms.
• Encourage knowledge sharing and cross-training to support consistent service delivery across venues.

Responsibilities Cont:

Technology Standards, Governance & Compliance

• Ensure venues operate in alignment with Compass Digital and Levy technology standards.
• Partner with Network Engineering and Information Security teams to support compliance with network architecture, security, and PCI requirements.
• Maintain oversight of POS configuration standards and system documentation in collaboration with POS vendors and internal teams.
• Coordinate regional participation in audits, compliance reviews, and remediation initiatives.

Vendor & Cross-Functional Collaboration

• Lead technical collaboration and escalation management with technology vendors supporting Levy venues.
• Partner with the Compass’ Vendor Strategy Office to ensure vendor accountability and service performance.
• Work closely with internal Compass teams including Digital Care, technology delivery teams, network engineering, and security to support venue operations and deployments.
• Maintain strong partnerships with Levy venue leadership including Vice Presidents of Hospitality, Directors of Operations, Regional Vice Presidents, and Division Presidents.

Data, Asset Management & Emerging Technology

• Promote a data-driven operational culture across the regional IT organization.
• Use operational data to identify trends related to system reliability, incident patterns, vendor performance, and event-day operations.
• Establish standardized processes for technology asset lifecycle and inventory management, ensuring accurate tracking of devices including POS systems, kiosks, networking infrastructure, and payment hardware.
• Identify opportunities to leverage emerging technologies, automation, and artificial intelligence to improve operational efficiency, incident response, and technology performance.
• Participate in pilots or proof-of-concept initiatives and provide field-level insights on new technologies.

Qualifications:

Required

• 10+ years of experience in IT operations, hospitality technology, or venue technology environments.
• 5+ years of leadership experience managing regional or multi-site technical teams.
• Experience supporting high-volume hospitality or live event environments.
• Strong knowledge of POS systems, payment infrastructure, and networking technologies.
• Experience managing vendor technical relationships and escalations.
• Strong communication skills and ability to collaborate with operational leadership and cross-functional teams.

Core Competencies

• Venue Technology Operations Leadership
• Technical Advisory & Solution Architecture
• Event-Day Technology Readiness
• Technology Governance & Standards
• Vendor Technical Management
• Data-Driven Operational Leadership
• Technology Asset Lifecycle Management
• Cross-Functional Collaboration