Director of IT Systems

Location: Flexible within the U.S. (Remote)
Reports to: Head of Digital Enablement and Operations
FLSA Status: Exempt

Organizational Overview

Jumpstart is a national early education organization working toward the day every child in America enters kindergarten prepared to succeed. We provide evidence-based language, literacy, and life skills programming for preschool children from underserved communities, delivered by a broad network of trained college students and community volunteers. Since our founding 1993, Jumpstart has supported over 209,000 children and mobilized more than 71,000 volunteers.

Position Overview

The Director of IT Systems is a mid-level leader responsible for the strategy, performance, and hands-on management of our IT infrastructure. This role ensures secure, reliable, and user-friendly technology for our national, remote-first staff and will lead efforts in systems administration, vendor management, and technical support operations. The Director of IT Systems will work closely with our three-person Digital Enablement & Operations team to ensure seamless technology delivery and continuous improvement.

This role is ideal for a mission-driven technologist with both strategic vision and hands-on technical skills. They will be a key enabler of Jumpstart's impact through reliable technology infrastructure and responsive user support.

What We’re Looking For

• Technically adept and hands-on – You can configure systems, troubleshoot issues, and optimize infrastructure.
  

• Strategic and proactive – You anticipate future needs and plan for scalable, secure systems.

• Service-oriented – You support colleagues with patience, clarity, and a solutions mindset.

• Operationally excellent – You maintain IT systems with discipline, security, and consistency.

• A strong partner – You work well with vendors, MSPs, and cross-functional teams to deliver results.
  

Key Responsibilities

IT Operations & Support Oversight – 35%

• Manage and coordinate with our managed service provider (MSP) to ensure proactive monitoring, timely issue resolution, and high-quality support.

• Oversee Jumpstart’s internal help desk: triage and resolve tickets directly, assign to appropriate resources, and monitor metrics to identify trends and recurring issues.

• Manage smooth technology onboarding and offboarding.

• Maintain accurate device, license, and equipment inventory, ensuring compliance with policies.

• Provide direct technical support to staff at all levels, including executive leadership.

Systems Administration & Configuration – 20%

• Administer Microsoft 365 (Entra/Azure AD, Teams, SharePoint, OneDrive, Outlook) and manage Group Policy and other remote configuration tools for security and performance.

• Maintain and troubleshoot on-premises and cloud-hosted servers in partnership with MSP.

• Alongside MSP, manage Active Directory, including user/group administration, security policies, and integration with cloud applications.

• Configure and support networking, file permissions, storage, and identity management.

• Implement and maintain automation and scripting solutions (e.g., PowerShell, Python) to improve efficiency.

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.

• Regularly update and enforce IT policies and security documentation.

Vendor & Technology Management – 15%

• Lead contract review, renewal, and selection processes for IT vendors, platforms, and tools.

• Monitor vendor and MSP performance to ensure service-level agreements are met.

• Evaluate and recommend new platforms and services based on cost, performance, and organizational needs.

Documentation, Training & Collaboration – 10%

• Maintain clear technical documentation, systems diagrams, and IT policies.

• Provide user training and guidance to improve staff confidence in using IT systems.

• Collaborate with the Director of Data Governance and Reporting to ensure system alignment with organizational workflows and data needs

• Support the Marketing and Communications team with the update of our websites

Qualifications

Required:

• 5+ years of experience in IT systems administration, infrastructure support, and vendor/MSP management.

• Advanced knowledge of Microsoft 365 ecosystem (Windows OS, Entra/Azure AD, Teams, SharePoint, OneDrive, Group Policy).

• Experience with server administration (physical and virtual) and cloud infrastructure such as AWS.

• Proficiency in Active Directory management, security policies, and identity integration with cloud platforms.

• Familiarity with networking principles, backup systems, and disaster recovery planning.

• Scripting and automation skills (PowerShell required; Python or similar a plus).

• Strong organizational, troubleshooting, and communication skills.

• Ability to work independently in a distributed, remote-first environment.

Preferred:

• Experience with Remote Desktop, SSH, or other remote management tools.

• Experience with containerized applications (Docker) and AWS.

• Knowledge of cybersecurity frameworks and IT compliance best practices.

• Experience supporting technical documentation and version control (e.g., Git).

• Ability to lift and transport up to 25 lbs of IT equipment as needed.

Travel

Approximately 4 to 6 days of travel a year

Start Date

ASAP

Location

Remote

Salary & Benefits

Salary Range: $93,500 - $126,500, commensurate with experience. Jumpstart also offers excellent benefits and a mission-driven work environment.

To Apply

Please complete an online application. A cover letter, resume, and responses to the screening questions are required to complete your application. Applications without a cover letter and responses to the screening questions may not be considered. Candidates will be reviewed on a rolling basis.

Jumpstart for Young Children, Inc. is an Equal Opportunity Employer that does not discriminate on the basis of actual or perceived race, creed, color, religion, gender identity or expression, national origin, ancestry, citizenship status, age, disability or handicap, sex, marital or parental status, amnesty, political affiliation, veteran status, military service, sexual orientation, genetic information, or any other characteristic protected by applicable federal, state or local laws.

Consistent with the Americans with Disabilities Act, applicants should reach out to HR @ jstart.org to request accommodations needed to participate in the application process.