We collaborate and innovate… At Top Hat Engineering, we’re revolutionizing supply chain management with cutting-edge software & automated solutions that empower businesses to optimize operations, reduce costs, and scale efficiently. Our platform is trusted by industry leaders, and we’re on a mission to transform how supply chains operate globally. Join our dynamic team and be part of the innovation driving the future of logistics and procurement. If you are interested in leveraging your talents to drive innovation, customer satisfaction, market growth, personal development and industry change in a dynamic teamwork environment, please explore the opportunities within our world class supply chain team! Position Summary: Top Hat Engineering is seeking a hands-on Director of IT to lead our day-to-day technology operations, oversee our cloud and corporate IT infrastructure, and ensure our engineering teams have the tools and systems they need to succeed. This role combines strategic IT leadership with direct technical involvement. You will lead the IT team while remaining comfortable troubleshooting infrastructure, managing servers, resolving complex technical issues, and supporting employees when needed. You will oversee our AWS and Microsoft Azure environments, Microsoft 365, Linux and Windows systems, endpoint infrastructure, and 3CX phone system. A key responsibility will be preparing, securing, deploying, and supporting Linux servers installed at customer locations to run Top Hat Engineering applications. This is a remote position with occasional travel to customer sites for infrastructure deployments, troubleshooting, and technical support. The ideal candidate is an experienced IT leader who enjoys building reliable, secure, and well-documented environments, improving operational efficiency through automation, and working directly with engineering teams and customers. Primary Duties and Responsibilities: IT Leadership and Strategy • Lead, mentor, and develop the IT team, managing priorities, resources, and service delivery. • Partner with the CIO and company leadership to establish the IT roadmap, budget, technology standards, and operational priorities. • Manage IT vendors, hardware procurement, software licensing, and service contracts. • Establish and maintain IT policies, documentation, asset inventories, and operational procedures. Cloud and Infrastructure • Manage and maintain AWS infrastructure, including EC2, S3, VPC, IAM, networking, and storage. • Administer Microsoft Azure and Entra ID services, including identity, access management, and cloud services as required. • Monitor cloud performance, security, availability, and costs. • Own backup, disaster recovery, and business continuity planning. • Improve infrastructure reliability and efficiency through automation and standardization. Microsoft 365 and Identity • Administer Microsoft 365, including Exchange Online, Teams, SharePoint, OneDrive, and Intune. • Manage user accounts, licensing, access permissions, MFA, conditional access, and single sign-on (SSO). • Integrate identity and access management with SaaS applications. • Maintain endpoint management, email security, and data protection policies. Linux, Windows, and Customer-Site Deployments • Provision, configure, and maintain Linux servers running Red Hat Enterprise Linux (RHEL) and Ubuntu, both in AWS and at customer facilities. • Manage the complete customer-site server deployment lifecycle, including hardware selection, operating system installation, security hardening, configuration, testing, upgrades, and troubleshooting. • Develop standardized server builds, deployment checklists, installation guides, and troubleshooting runbooks. • Work directly with customer IT teams to validate server readiness, networking, firewall rules, access requirements, and security policies. • Troubleshoot server, operating system, networking, and application infrastructure issues remotely and on-site as needed. • Travel to customer locations as needed to support deployments, resolve infrastructure issues, and coordinate technical activities. • Administer Windows Server and Windows 10/11 environments, including Active Directory, Group Policy, and system updates. • Automate routine infrastructure and administration tasks using Bash, PowerShell, Python, Ansible, Terraform, or similar tools. End-User Support and Hardware • Serve as the senior escalation point for complex hardware, software, network, and access issues. • Diagnose and repair laptops and desktops, including component replacement when necessary. • Manage device procurement, imaging, deployment, inventory, maintenance, and retirement. • Oversee the help desk, ticket queue, service-level targets, and employee support experience. Telephony and Security • Administer and maintain the 3CX phone system, including extensions, call routing, IVR, SIP trunks, desk phones, and softphones. • Maintain endpoint protection, firewalls, VPNs, identity controls, and secure remote access. • Lead vulnerability management, patch compliance, security incident response, and remediation activities. • Conduct security awareness training and maintain security policies, access reviews, and operational documentation. Collaborate with customers to address infrastructure security requirements for on-premises and cloud deployments. Qualifications: • 15+ years of IT experience, including at least 5 years leading an IT team. • Strong hands-on experience with AWS infrastructure and cloud operations. • Experience administering Microsoft 365, Entra ID, identity management, SSO, and MFA. • Strong Linux administration skills, particularly with RHEL and/or Ubuntu. • Experience provisioning, securing, deploying, and troubleshooting servers in on-premises or customer-managed environments. • Experience managing Windows Server, desktop operating systems, networking, and endpoint infrastructure. • Knowledge of security best practices, patch management, vulnerability remediation, backups, and disaster recovery. • Strong troubleshooting, documentation, organizational, and communication skills. • Ability to work directly with customers and coordinate technical deployments with their IT teams. • Willingness and ability to travel occasionally to customer sites. • Ability to safely lift, carry, push, and pull objects weighing 40+ pounds. • Ability to stand and walk for extended periods of time, including throughout full work shifts. • Ability to follow safety procedures, wear required personal protective equipment and maintain a clean and organized work area. • Reliable attendance and punctuality, including flexibility to work extended hours, overtime, or varying shifts when required. Preferred Qualifications • Experience leading IT operations in an engineering, software, or technical professional services organization. • Experience with infrastructure automation tools such as Ansible and Terraform. • Familiarity with virtualization platforms such as VMware, Nutanix, or Hyper-V. • Experience with IT service management platforms such as ServiceNow. • Familiarity with IT security and compliance frameworks. • Relevant certifications, such as AWS Solutions Architect, Microsoft Azure Administrator, Microsoft 365 Administrator, RHCSA/RHCE, CompTIA Security+, ITIL Foundation, or 3CX certifications. The Qualities That Will Make You Successful • Hands-on leadership: Equally comfortable setting direction, coaching a team, and troubleshooting a failing server or laptop. • Strong ownership: Accountable for reliability, security, service quality, and successful customer deployments. • Customer focus: Understands that responsive support and reliable infrastructure are essential to customer success. • Security mindset: Makes security and access control part of everyday IT operations. • Automation-oriented: Looks for ways to reduce manual effort and establish repeatable, scalable processes. • Calm under pressure: Responds methodically and decisively to outages, security incidents, and critical technical issues. • Commitment to documentation: Builds maintainable systems supported by clear procedures, runbooks, and configuration records. Why Join Top Hat Engineering? This is an opportunity to take ownership of a broad technology environment and make a direct impact on how our company operates and delivers solutions to customers. You will work across cloud infrastructure, corporate IT, cybersecurity, and customer-facing deployments, with the opportunity to shape our technology roadmap and build a more reliable, secure, and efficient IT organization. Top Hat Engineering is an equal opportunity employer. We welcome qualified candidates from all backgrounds, including veterans and transitioning service members. Salary: $130K - $150K AnnuallyOriginally posted on Himalayas