Head of Information Technology (Remote)

The Director of Information Technology is responsible for the oversight of all technology operations and infrastructures to ensure alignment with established goals and best practices. This individual works with cross‑functional business leaders to solve complex business problems, champion AI system adoption, and support the organization’s goals. The role reports directly to the Chief Digital and Transformation Officer and requires experience managing an IT infrastructure in a remote/hybrid environment, with a critical focus on advanced data security, AI governance, and protection of highly confidential client information. It is a hands‑on, player‑coach role balancing strategic leadership with direct ownership of enterprise systems, infrastructure, automation initiatives, cybersecurity, and operational excellence.

This remote‑first organization hires specifically within 60 miles of the following cities: Employees may work remotely or in‑person as appropriate.

Manage and execute the strategic direction of the company’s enterprise IT policies and systems to support organizational goals, while serving as the senior technical resource and escalation point for infrastructure, networking, endpoint, identity, and enterprise applications.

Partner with key functional directors and business leaders to communicate IT needs, evaluate technology investments (including implementations, migrations, upgrades and modernization projects) and support organizational growth.

Own the architecture, administration, and continuous improvement of the technology stack, including Google Workspace, Jamf, Okta, Slack, Zoom, Cisco Meraki, and enterprise SaaS platforms.

Manage hardware and software lifecycle, licensing, procurement, asset management, and vendor relationships.

Lead the evaluation, implementation, and governance of Artificial Intelligence (AI) systems and emerging AI tools across the organization to drive operational efficiency and innovation.

Develop AI‑powered workflows, internal applications, and automations using platforms such as Replit to improve productivity and operational efficiency.

Establish robust data security frameworks for AI models and external API integrations ensuring proprietary and sensitive company data remains protected against unauthorized access and AI‑specific vulnerabilities.

Establish, maintain, and enforce comprehensive information security and disaster recovery programs to protect company data, networks, applications, proprietary intellectual property, and highly confidential client data from internal and external risks.

Implement and manage robust monitoring systems to oversee the software, applications, and tools being utilized by internal teams, mitigating shadow IT and ensuring all tools meet the company’s security standards.

Partner with the Human Resources department to establish secure, compliant, and reliable protocols for HR to access necessary organizational and employee data.

Evaluate information risk on a regular time schedule and promote continuous information security awareness and compliance training within the organization.

Speak to internal and external stakeholders about data security policies, procedures and standards, including AI ethics, data privacy, and compliance.

Identify and recommend new technologies and services that will improve efficiency, processes, and operations; Provide direct support to employees on technology hardware and software to ensure operating availability, and implement training programs (including the safe and secure use of AI platforms).

Manage the quarterly IT budget to align with open targets, and compile formal business cases for hardware, software, or system upgrades to present to upper leadership.

Create personalized coaching plans for direct reports to continuously improve performance and facilitate career progression.

Play an integral role in the hiring process, and oversee new direct reports’ onboarding and training in order to achieve fast ramp goals.

10+ years of progressive IT leadership experience, with a strong preference for managing IT infrastructure within a cloud‑first, professional services environment.

Demonstrated leadership skills with the ability to define and execute a high‑level technology vision, lead and develop high‑performing teams, and direct complex, cross‑functional projects from inception to deployment.

Hands‑on experience leading enterprise‑wide AI initiatives (from vendor selection to deployment) combined with expertise in data loss prevention (DLP), software monitoring tools, and secure data‑access protocols.

Experience deploying enterprise AI platforms such as "ChatGPT Enterprise", "Claude", "Google Gemini", or similar technologies, and developing internal automations or lightweight business applications using platforms such as Replit.

Experience in establishing, monitoring and managing corporate IT budgets.

Advanced knowledge of macOS, Google Workspace, Microsoft Operating Systems and Office, and Adobe Creative Cloud. Experience administering Jamf, Okta, Zoom, Slack, Cisco Meraki, and identity and access management. Microsoft or Cisco certifications are a plus.

Ability to think critically and solve and overcome complex IT problems and challenges.

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