Director of Information Technology

53d•$160,000 - $170,000•Hybrid

About The Position

The Director of Information Technology serves as the second-in-command of the IT department and a key operational partner to the Vice President of IT. This role is responsible for the day-to-day performance of IT operations, support services, infrastructure, endpoint management, hardware provisioning, vendor relationships, and major technology projects across the organization. This is a hands-on leadership role, not a position focused solely on management or vendor coordination. The Director must be technically strong, closely involved with the company's systems, and able to step into complex issues, make sound decisions, and drive work through completion without constant direction or follow-up.

Requirements

7+ years of progressive experience in IT operations, systems administration, technical support, infrastructure, or a related field.
3+ years of experience leading an IT support, infrastructure, or systems administration team.
Demonstrated experience serving as a hands-on technical leader in a multi-site or distributed organization.
Advanced working knowledge of Microsoft 365, Microsoft Entra ID, Microsoft Intune, Exchange Online, PowerShell, Group Policy, Active Directory, and Windows administration.
Hands-on experience with Windows Autopilot, endpoint configuration and compliance, application deployment, device provisioning, patch management, feature updates, and large-scale Windows rollouts.
Strong knowledge of networking fundamentals, endpoint security, identity and access management, infrastructure troubleshooting, and cybersecurity best practices.
Proven ability to lead major IT projects from planning through completion and maintain accountability for timelines, risks, communications, and outcomes.
Experience managing IT vendors, telecom providers, hardware procurement, asset lifecycle, and service contracts.
Strong troubleshooting, decision-making, organizational, communication, and leadership skills.
Ability to travel 25% of the time
Ability to explain technical issues in practical business terms and work effectively with executives, department leaders, store personnel, vendors, and technical staff.
Ability and willingness to travel regularly to company locations. Travel frequency will vary based on store openings, projects, deployments, and support needs.
Ability to perform hands-on installation, configuration, troubleshooting, and equipment deployment activities as needed.
Ability to manage competing priorities and respond effectively during outages, incidents, and other time-sensitive situations.
Valid driver's license and ability to travel by air or automobile, as required.

Nice To Haves

Microsoft certifications related to Microsoft 365, Azure, Entra ID, Intune, Windows, security, or endpoint administration. Certifications are valued when supported by strong practical experience.
Experience with Microsoft Azure services and administration, including Logic Apps, Blob Storage, cloud integrations, automation, and hybrid environments. Experience with Azure-based data platforms, such as data lakes, data warehouses, and related analytics or integration services, is a plus.
Experience supporting retail, warehouse, point-of-sale, or other multi-location business operations.
Experience administering a Jira Service Management environment, including service projects, request types, workflows, queues, automation rules, permissions, SLAs, reporting, and ongoing platform improvement.
ITIL, CISSP, PMP, or other relevant technical, security, or project management certifications.
Eastern Time Zone strongly preferred.

Responsibilities

Act as the primary operational partner and backup to the Vice President of IT, helping lead the department and maintain continuity of IT operations.
Lead, coach, and hold accountable the IT support and infrastructure team, with clear expectations for service quality, technical accuracy, documentation, and follow-through.
Oversee IT service desk operations in Jira, including ticket prioritization, escalations, response and resolution performance, recurring issue analysis, and customer service standards.
Remain closely involved with all major systems, applications, integrations, vendors, and support processes to ensure the department has effective internal ownership and is not overly dependent on any one employee or outside provider.
Communicate risks, delays, outages, and other concerns early and provide clear, accurate status updates to leadership.
Administer, troubleshoot, secure, and improve the Microsoft 365 environment at an advanced, hands-on level.
Manage Microsoft Entra ID, including identity lifecycle, authentication, Conditional Access, multifactor authentication, enterprise applications, role assignments, guest access, and access controls.
Lead Microsoft Intune administration, including enrollment, configuration profiles, compliance policies, application deployment, Windows Autopilot, remediation scripts, device lifecycle management, and endpoint security.
Develop, maintain, and use PowerShell scripts to automate administration, reporting, provisioning, remediation, and other repetitive IT processes.
Administer and troubleshoot Microsoft Exchange, including mail flow, permissions, shared mailboxes, distribution groups, security settings, and related integrations.
Manage and troubleshoot Group Policy, Active Directory, DNS, and DHCP.
Plan and execute large-scale Windows deployments, feature updates, security patches, application rollouts, configuration changes, and device replacement initiatives.
Monitor device compliance, vulnerabilities, encryption, endpoint protection, privileged access, and patching to maintain a secure and supportable environment.
Oversee the stability, security, performance, and supportability of network infrastructure, internet connectivity, wireless systems, servers, printers, POS-related hardware, and other store technology.
Lead or assist with the technical response to outages, cybersecurity incidents, infrastructure failures, and complex escalations.
Identify technical debt, unsupported systems, recurring failures, and control gaps, and develop practical plans to address them.
Maintain accurate technical documentation, standards, diagrams, procedures, recovery information, and system ownership records.
Oversee hardware provisioning, configuration, deployment, replacement, recovery, and retirement for laptops, desktops, POS terminals, printers, network equipment, mobile devices, and related technology.
Ensure equipment standards, asset records, inventory controls, warranties, spare equipment levels, and replacement cycles are maintained.
Manage technology purchasing and vendor relationships with attention to pricing, standardization, lead times, service quality, and total cost of ownership.
Work alongside the team when needed to resolve escalated support issues, provision equipment, or address operational problems.
Participate in a 24/7 on-call rotation and respond to critical incidents, outages, and business-impacting technology issues outside normal business hours as needed.
Own major IT projects from planning through implementation, including scope, timelines, resources, testing, communications, training, documentation, risk management, and transition to support.
Coordinate effectively with Operations, Supply Chain, Finance, Human Resources, Marketing, Loss Prevention, and other departments to understand business needs and deliver practical technology solutions.
Set realistic expectations and ensure proposed solutions align with company standards, security requirements, operational needs, and long-term technology strategy.
Manage vendors and service providers, challenge incomplete or inaccurate work, and hold partners accountable for commitments, performance, cost, and outcomes.
Drive standardization and process improvement across company locations to improve reliability, security, efficiency, and supportability.
Travel regularly to stores, warehouses, and corporate locations for new store installations, infrastructure upgrades, equipment deployments, project work, assessments, and other activities requiring on-site participation.
Provide or coordinate on-site support when remote troubleshooting is unsuccessful or when an issue is business-critical and requires hands-on technical involvement.
Be available for occasional early-morning, evening, weekend, or short-notice work based on store openings, outages, implementations, and project schedules.