Head of Information Technology (Remote)

AI2IO helps organizations navigate the complex landscape of technology solutions, from foundational IT services and system support to advanced software integration, automation, and cutting-edge AI implementations. Our expertise spans IT infrastructure management, custom software development, seamless system integrations, and optimization of low-code business automation, empowering clients to maximize their existing technology investments.
Director of Information Technology
Remote - work virtually from anywhere in the United States
The Director of Information Technology is responsible for the tactical execution of the strategic technology roadmap defined by the CTO. This role translates strategy into operational reality, directing multidisciplinary teams across security, cloud infrastructure, SaaS Business Applications, M365 application management, and IT operations to deliver reliable, secure, and scalable technology services across the Company's family of affiliated organizations.
The Director owns the day-to-day operational direction of the IT function, builds and leads high-performing teams, and is personally accountable for the stability, security, and service quality of the technology environment the organization depends on. the Director must possess the technical depth to credibly direct teams operating on the Microsoft platform, but hands-on execution is delegated to engineers, administrators, and operations staff on the team. The Company is projecting significant headcount growth over the next 12 months, and this role is expected to personally drive a substantial share of that hiring for the IT function.
The Director leads the IT organization toward maturity in IT Service Management, establishing and continuously improving ITIL-aligned processes for incident, problem, change, request, and asset and configuration management. The Director partners closely with the Director of Software Engineering on infrastructure needs and the roadmap for software development operations, partners with the Director of Tech Talent & People Operations on staffing and hiring pipelines for the IT organization, and works across the business to align technology delivery with operational and strategic priorities.
This role is responsible for establishing and maintaining IT operational standards, securing and modernizing the technology state across the Microsoft 365 ecosystem and Azure PaaS and IaaS environments, and ensuring consistency, governance, and operational integrity across the Company's infrastructure and end-user services, in alignment with SOC 2 and other applicable security and compliance standards. Key areas of responsibility include IT operations and end-user services, security and cloud infrastructure, business continuity and disaster recovery, M365 application management, cloud hosted SaaS applications, IT service management maturity (ITSM/ITIL), team building and development, vendor management, and executive-level reporting on IT initiatives and roadmap progress. This role also includes oversight of procurement, employee onboarding and offboarding, contribution to IT budget planning, and partnership with software engineering leadership on the infrastructure supporting development operations.
The Director of Information Technology operates with a high degree of autonomy, setting operational direction across the IT function, prioritizing work, and ensuring effective collaboration across security, infrastructure, applications, and operations teams.
This role is intended as a leadership development track toward broader executive technology responsibility. As the Director demonstrates impact and readiness, the scope of the role may expand to include oversight of additional technical functions such as software engineering, business intelligence, and product, with the potential to grow toward senior executive scope over time.
Advancement is not guaranteed and depends on demonstrated performance, organizational needs, and business conditions. This position is structured to develop and prepare a leader for that broader scope, but does not constitute a commitment to a specific future role.
IT Operations, Infrastructure & Security

Lead IT Operations: Direct day-to-day IT operations including end-user support, procurement, and employee onboarding and offboarding, ensuring responsive, reliable service across the organization
Own Security & Cloud Infrastructure: Direct the security and cloud infrastructure functions, ensuring the technology environment is secure, resilient, performant, and cost-optimized across hybrid on-premises and Azure cloud environments, in alignment with SOC 2 and other applicable security and compliance standards
Manage M365 Applications: Oversee administration and management of the Microsoft 365 ecosystem, ensuring application reliability, security, governance, and effective adoption across the organization
SaaS Business Applications: Oversee administration and configuration of hosted 3rd party applications that are crucial to continued business functions
Business Continuity & Disaster Recovery: Establish and maintain business continuity and disaster recovery plans for the technology environment, including backup, failover, and recovery procedures, and ensure they are tested on a regular cadence
Execute the Roadmap: Own the tactical implementation of the technology roadmap and strategic priorities established by the CTO, converting strategy into actionable plans, timelines, and measurable outcomes
Drive ITSM/ITIL Maturity: Lead the organization toward maturity in IT Service Management, establishing and continuously improving ITIL-aligned processes for incident, problem, change, request, and asset and configuration management, and defining service-level metrics and operational KPIs
Partner with the Director of Software Engineering: Align on infrastructure needs and the roadmap for software development operations, maintaining working familiarity with development platforms and practices including Azure DevOps, SQL Server, and IIS
Partner with the Director of Tech Talent & People Operations: Coordinate on staffing plans and hiring pipelines for IT roles, and partner on career track development and role leveling for the IT organization
Serve as a trusted technology partner to leadership across the organization; Build and Develop the IT Team: Recruit, build, and mentor high-performing, multidisciplinary teams at the pace required to support rapid organizational growth, establishing clear structure, roles, accountabilities, and career paths, and providing direct mentorship and performance management
Manage vendor and technology partner relationships across the IT function, including contract negotiation, renewal management, and performance oversight
Contribute to IT budget planning and forecasting in partnership with the CTO, including cost forecasting for infrastructure, licensing, and vendor spend
Report to Leadership: Provide executive-level reporting on IT initiatives, roadmap progress, service performance, risks, and resource needs to the CTO and senior stakeholders, translating technical details for both technical and non-technical audiences
Proven experience leading multidisciplinary IT teams across security, cloud infrastructure, application management, and IT operations (end-user support, procurement, onboarding and offboarding)
Deep hands-on and leadership experience with the Microsoft ecosystem, including the full Microsoft 365 suite and Azure PaaS and IaaS environments
SOC 2) and experience operating IT environments under audit
Substantial ITSM/ITIL experience with a demonstrated track record of driving IT service management process maturity
Working knowledge of software development operations and supporting platforms, including Azure DevOps, SQL Server, and IIS, sufficient to partner effectively with software engineering leadership
Demonstrated experience personally leading high-velocity technical hiring, building out and staffing multidisciplinary teams at pace, including experience supporting significant headcount growth (e.g., Experience negotiating and managing vendor and technology partner contracts, including renewal negotiation and vendor performance management
Strong executive communication skills, including the ability to provide executive-level reporting and influence senior leadership
Familiarity with SDLC and Agile delivery practices
Ability to leverage AI and emerging technologies to streamline workflows, optimize operational processes, and contribute to company-wide innovation
Demonstrated aptitude for learning new technology and adapting to evolving requirements
Travel / Relocation Requirements
Up to 5%, this may include travel to any or all 50 US states
Travel is defined as physically leaving home on behalf of business activities including but not limited to client sites, meetings with other employees, meeting for business development purposes, running errands on behalf of the business, attending industry conferences, etc.
Bachelor's degree in IT, Information Systems, Computer Science, or related discipline

10+ years of experience in IT infrastructure, operations, or technology leadership, including 5+ years leading and growing multidisciplinary IT teams

Choice of comprehensive medical plans (including two PPO-style plans and a HDHP w/ HSA option)

• Flex spending accounts (FSA)
• Dental and vision plans
• Comprehensive medical, dental and vision benefits extended to spouse / domestic partner and dependent children up to age 26
• 401k with company match and self-directed brokerage account option
• Company paid life insurance coverage for employees and their eligible dependents
• Short and long-term disability, AD&D coverage
• Professional development opportunities, tuition reimbursement and professional licensing assistance
• CO, CA, IL, NY, WA, and Washington DC residents only: We encourage diversity in our workforce.

Unsolicited resumes include any resume or hiring document sent to AI2IO in the absence of a signed Service Agreement where AI2IO has expressly requested recruitment/staffing services specific to the position at hand. 141,750 - 172,462.50 USD per year (Remote (United States))