IT Managed Services - Virtual CIO

The Director of IT will lead a talented team of IT professionals responsible for supporting the cloud-based IT Infrastructure of a rapidly scaling software development company. Reporting directly to the Chief Information Security Officer & Head of IT, you will be responsible for defining and driving the future of our IT infrastructure by identifying and helping set strategy, envisioning complex ecosystems, and inspiring teams to push the boundaries of what's possible. You will possess a clear vision of best-practice IT methodologies and have the courage to pursue innovative approaches to make our technology programs more efficient, resilient, and cutting-edge. This position will have an enormous impact on our success by ensuring not only that the company can grow and work efficiently, but also by ensuring that the AWS infrastructure provides a dependable platform for our flagship web application to meet our clients accounting and payroll needs. This role is remote within the United States.
IT Operations & Infrastructure
Lead and continuously improve IT service delivery across a 200+ person distributed remote workforce, ensuring consistent SLAs, first-call resolution rates, and end-user satisfaction
Own the health, performance, and lifecycle of our endpoint fleet, including patch management, imaging, remote remediation, and hardware provisioning
Oversee automated onboarding, offboarding, and device lifecycle management
Partner with business stakeholders on internal systems architecture, access management, and IT-adjacent cloud services (e.g., AWS, Google Workspace, Azure, M365)
AI Adoption & Business Process Automation
Apply an automation-first lens to every IT workflow: onboarding sequences, ticket triage, patch deployment, reporting, and SaaS provisioning should be automated by default, manual by exception
Evaluate and recommend emerging AI and automation tools that can accelerate IT operations or deliver measurable business value
IT Security Collaboration
Serve as a key operational partner to the CISO on security initiatives, translating security policy into operational IT controls, configurations, and staff behaviors
Own vulnerability response workflows for IT-managed infrastructure, coordinating with the Information Security team on CVE triage, remediation timelines, and change management
Support SOC audit readiness by maintaining accurate asset inventories, access records, and change logs within Jira and Rippling
Team Leadership & Stakeholder Management
Directly manage and develop a team of helpdesk administrators and sysadmins, fostering a culture of ownership, continuous improvement, and measurable outcomes
Conduct regular 1:1s, performance reviews, and career development conversations; actively mentor team members toward growth opportunities
Define, track, and report to senior leadership on IT KPIs, including ticket SLAs, First Call Resolution rate, fleet compliance, patch coverage, and automation ROI, on a recurring basis
Oversee the IT and SaaS portfolio budget, identifying cost reduction and consolidation opportunities without compromising capability or security
7+ years in IT infrastructure, systems administration, or IT operations roles, with at least 4 years in a management capacity

• Demonstrated experience leading IT in a remote-first or distributed environment; Deep working knowledge of Kaseya VSA or equivalent RMM platforms for fleet management, scripting, and patch automation
• Hands-on experience with Google Workspace administration at the enterprise level (OU structure, MDM, Vault, shared drives, admin console)
• Experience with ITSM platforms (Jira Service Management strongly preferred), including ticket workflows, SLA configuration, and reporting
• Familiarity with internal IT use cases: IAM, SSO, EC2, S3, and VPN/network connectivity
• Working knowledge of EDR platforms and broader endpoint security posture management.
• Experience implementing or managing device lifecycle programs, procurement, provisioning, asset tracking, and EOL, at 200+ device scale
• Strong project management skills: capable of running concurrent initiatives across teams with clear milestones, owners, and accountability
• Bachelor's degree in Computer Science, Information Technology, or a related field; AI & Automation Fluency

You use AI tools daily, not experimentally. You can articulate how you've used AI to accelerate a project, reduce manual work, or solve a problem
Direct experience with enterprise AI platforms (Claude, Copilot, or equivalent), including policy development, rollout, and user enablement
Hands-on experience with no-code/low-code automation platforms (n8n, Zapier, Make, or equivalent), you have built real automations, not just configured templates
Ability to write or review automation scripts (PowerShell, Bash, Python) to support fleet management, provisioning, and IT operations workflows
Comfort evaluating AI/automation ROI: you can estimate time savings, reduction in error rates, and business impact for proposed automations
Operates with a service mentality and executive presence: you're as effective in a board update as you are troubleshooting with a helpdesk technician
Bring a data-driven approach to decision-making. Proactive communicator: you surface risks early, document decisions, and keep stakeholders informed without being prompted