Position SummaryThe Senior Director of IT is a hands-on technology leader responsible for the reliability, security, support, and continuous improvement of the company's technology environment. Reporting to the Chief Information Officer, this role will lead day-to-day IT operations across stores, warehouses, offices, and remote users; ensure business-critical systems and infrastructure operate optimally with minimal downtime; and build trusted relationships with leaders across the organization.
This leader will oversee the responsibilities currently performed by the IT operations and field-support function, including infrastructure coordination, store and warehouse technology support, new-location readiness, incident escalation, vendor management, and technology standards. The role will also own security operations, IT budgeting and licensing, contract negotiations, and the operating relationships necessary to align technology with business priorities.
Key ResponsibilitiesIT Operations and Support- Lead the IT support function and establish clear, responsive processes for incidents, service requests, escalations, and root-cause follow-up.
- Provide leadership for support across retail stores, warehouses, offices, and remote employees, including hardware, software, connectivity, endpoints, printers, point-of-sale peripherals, and user access.
- Develop service standards, operating procedures, knowledge articles, and escalation paths that improve consistency and user experience.
- Monitor service performance and recurring issues; drive corrective actions and communicate status, impact, and resolution plans to stakeholders.
Infrastructure and Availability- Own the performance, availability, and lifecycle of IT infrastructure, including networks, internet connectivity, SD-WAN, wireless, servers, cloud services, endpoints, identity, backup, and monitoring platforms.
- Ensure technology environments are designed, maintained, and supported for reliability, scalability, security, and business continuity.
- Coordinate infrastructure changes, upgrades, maintenance windows, and testing with internal teams and vendors to minimize operational disruption and downtime.
- Establish standards for configuration, documentation, redundancy, disaster recovery, and change management.
- Support new store, warehouse, office, and relocation projects from planning through readiness testing and go-live.
Cybersecurity and Risk Management- Lead the company's day-to-day security program in partnership with the CIO and relevant business stakeholders.
- Manage endpoint security, identity and access controls, patching, vulnerability remediation, security monitoring, incident response, and security awareness activities.
- Maintain practical security policies, procedures, standards, and evidence needed for audits, vendor reviews, and regulatory or contractual requirements.
- Coordinate security incident investigation, containment, communication, recovery, and post-incident improvements.
- Evaluate the security posture of technology vendors and participate in third-party risk reviews, including SOC reports and remediation tracking.
Budget, Licensing, and Asset Management- Manage the IT infrastructure and operations budget, including forecasting, expense control, renewals, capital planning, and business-case development.
- Maintain visibility into software, hardware, cloud, connectivity, security, and support licensing; identify unused or overlapping services and opportunities for savings.
- Establish asset lifecycle practices for procurement, deployment, inventory, maintenance, replacement, recovery, and disposal.
- Prepare regular budget, service-performance, risk, and roadmap updates for the CIO and executive leadership.
Vendor and Contract Management- Own day-to-day relationships with IT vendors, service providers, managed service partners, carriers, and technology suppliers.
- Set expectations for service levels, escalation management, deliverables, reporting, and issue resolution.
- Lead or support contract negotiations, renewals, statements of work, pricing reviews, service credits, and termination or transition planning.
- Evaluate vendor performance and recommend changes when services, support, security, cost, or business alignment do not meet expectations.
Business Partnership and Leadership- Build and maintain strong working relationships with business leaders throughout the organization, including Retail, Operations, Distribution, Finance, Human Resources, and Executive Leadership.
- Translate business needs into practical technology priorities and communicate technical issues in clear business terms.
- Partner with leaders to understand operational pain points, prioritize improvements, and measure whether technology changes are delivering the intended value.
- Lead, coach, and develop IT team members; establish accountability, collaboration, and a service-oriented culture.
- Represent IT professionally and promote reliable, secure, and scalable technology practices across the organization.
Expected Outcomes- Business-critical systems and infrastructure operate reliably, with minimal avoidable downtime and clear ownership of incidents.
- IT support is responsive, measurable, and consistent across stores, warehouses, offices, and remote employees.
- Security controls, incident response, vendor risk management, and technology documentation are maintained at a practical and effective standard.
- IT spending, licenses, assets, and vendor commitments are actively managed and aligned to business priorities.
- New locations, infrastructure changes, and technology projects are delivered with disciplined planning, testing, communication, and support readiness.
- Business leaders view IT as a trusted partner that understands operational needs and follows through on commitments.
Required Qualifications- Bachelor's degree in Information Technology, Computer Science, Business, or a related field, or equivalent professional experience.
- 10 or more years of progressive IT experience, including significant responsibility for infrastructure, support, cybersecurity, or IT operations.
- Experience leading teams and managing technology operations across multiple locations, preferably in a retail, distribution, or similarly distributed environment.
- Demonstrated experience managing IT budgets, licensing, vendors, contracts, and service providers.
- Strong understanding of networking, cloud and SaaS platforms, endpoint management, identity and access management, cybersecurity controls, backup, and disaster recovery.
- Experience leading incident response, root-cause analysis, change management, and operational improvements.
- Excellent communication, organization, negotiation, and stakeholder-management skills.
- Ability to balance strategic planning with hands-on execution in a fast-moving operating environment.
Preferred Qualifications- Experience supporting retail stores, warehouses, point-of-sale environments, or other distributed field operations.
- Relevant certifications such as ITIL, CISSP, CISM, CompTIA Security+, or vendor-specific infrastructure and cloud certifications.
- Experience with Microsoft 365, Azure, Entra ID, Intune, Power BI, SD-WAN, endpoint security, service management, and third-party risk reviews.
- Experience leading technology transitions, network migrations, new-location openings, or vendor replacement programs.
Work Location and TravelThis is a remote position. The Senior Director of IT must be able to travel to the Frederick, Maryland office as needed and may occasionally travel to stores, warehouses, vendor locations, or other company facilities based on business requirements, projects, incidents, or leadership needs.
