An opportunity is available for a Director of IT Systems at Jumpstart, a national early education organization dedicated to ensuring every child enters kindergarten prepared to succeed. This mid-level leadership role is responsible for the strategy, performance, and hands-on management of the organization’s entire IT infrastructure.

This is a full-time, remote position, flexible anywhere within the U.S. The salary range is $93,500 – $126,500 annually.

Role Summary and Hands-On Strategy

Reporting to the Head of Digital Enablement and Operations, this Director ensures secure, reliable, and user-friendly technology for a national, remote-first staff. The role demands both strategic vision and deep technical proficiency in administration, security, and support.

Key Responsibilities

• IT Operations & Support Oversight (35%): Manage and coordinate with the Managed Service Provider (MSP). Oversee the internal help desk, triaging and resolving tickets directly, managing metrics, and handling seamless technology onboarding/offboarding for the entire staff.
• Systems Administration & Configuration (20%): Serve as the principal administrator for the Microsoft 365 ecosystem (Entra/Azure AD, Teams, SharePoint, Group Policy). Configure and support networking, file permissions, and identity management. Implement and maintain automation and scripting solutions (e.g., PowerShell).
• Security, Risk & Continuity (20%): Lead cybersecurity and risk management efforts, including incident response, access controls, and vulnerability mitigation. Verify and test backups and disaster recovery processes to ensure business continuity.
• Vendor & Technology Management (15%): Lead contract review, renewal, and selection processes for IT vendors and platforms. Monitor vendor and MSP performance against service-level agreements.

Required Experience and Technical Qualifications

The ideal candidate is a mission-driven technologist with a proven background in managing IT infrastructure, specializing in the Microsoft and cloud ecosystem.

• Experience: 5+ years of experience in IT systems administration, infrastructure support, and vendor/MSP management.
• Core Systems Expertise: Advanced knowledge of Microsoft 365 ecosystem (Windows OS, Entra/Azure AD, Teams, SharePoint, Group Policy) and proficiency in Active Directory management.
• Infrastructure & Automation: Experience with server administration (physical and virtual) and cloud infrastructure (such as AWS). Scripting and automation skills (PowerShell required).
• Technical Skills: Familiarity with networking principles, backup systems, and disaster recovery planning.
• Work Style: Strong organizational, troubleshooting, and communication skills, with the ability to work independently in a distributed, remote-first environment.