Senior Systems Administrator

Reporting to the Infrastructure Manager, the Senior Systems Administrator ensures that DREAM's technology infrastructure is secure, reliable, and ready to scale across four campuses of a K-12 charter school network. This role safeguards the systems and student data that classrooms and operations depend on, modernizes how infrastructure is managed through automation and AI, and helps guide the organization through growth and technology transitions. The ideal candidate is a mission-driven professional who believes students of all backgrounds can achieve at high levels. They bring broad, hands-on expertise across networking, security, and systems, take full ownership of their work, and raise the team's standards through sound judgment, strong collaboration with partners and vendors, and a commitment to continuous learning. Responsibilities • Network: Design, operate, and secure the multi-campus network, including firewalls, VPN, switching, and wireless. • Cybersecurity: Maintain the organization's security posture, including EDR, vulnerability and patch management, security monitoring, and incident response. • Monitoring: Maintain monitoring and alerting for network and system health, and investigate outages with clear incident reports. • Identity: Administer Active Directory, Google Workspace, and Okta, including SSO and provisioning. • Systems and endpoints: Operate virtualization, servers, and backup and disaster recovery, and manage macOS and Windows fleets through MDM. • Cloud and data: Administer Google Cloud (GCP) environments, including BigQuery, and use SQL to support integrations, reporting, and automation. • Automation and AI: Lead automation and AI projects from scoping to production. • Leadership: Coach IT staff and resolve escalated support requests. • Delivery: Plan sprints, manage vendors, document and communicate changes, and report status to leadership. Qualifications Required • At a minimum, a High School Diploma and 5+ years of experience in IT and systems administration; or Associates Degree or higher and 3+ years of experience IT and systems administration; • Hands-on experience with next-generation firewalls (such as Palo Alto, Fortinet, or Cisco), VPN, switching, wireless, and multi-site networks. • Cybersecurity operations experience, including EDR, vulnerability management, incident response, and security monitoring through a SIEM (such as Wazuh, Splunk, or Microsoft Sentinel). • Experience building and tuning monitoring and alerting for network and server health (such as Zabbix, PRTG, or Datadog). • Strong identity experience with Active Directory, Google Workspace Admin, and an IdP such as Okta, Entra ID, or JumpCloud. • Virtualization experience (VMware, Hyper-V, or Proxmox) and backup and disaster recovery practice. • Endpoint management experience for macOS and Windows through MDM platforms (such as Jamf, Kandji/Iru, Mosyle, or ManageEngine Endpoint Central). • Experience automating administrative work with scripting (PowerShell, Python, or Bash) and building automation or AI-assisted workflows that replaced manual processes. • Database and cloud experience, including writing SQL and working with BigQuery in Google Cloud (GCP). • Experience coaching or mentoring other IT staff and handling escalated support. • Track record of leading projects from planning to delivery, including sprint planning and status reporting. • Strong documentation habits and clear writing for both technical and non-technical readers. • Demonstrated ability to learn new tools quickly and adapt to changing priorities. • A strong belief in the mission and values of DREAM, including the desire to make a difference in the lives of our students, families, and community. Preferred • Proven experience leading an AI or automation project end to end, from scoping to production, with attention to data privacy, cost, and output quality. • Working knowledge of workflow and integration platforms (n8n, Zapier, or similar) and REST APIs. • Practical experience with additional cloud platforms, such as AWS or Azure. • Background as an infrastructure lead, owning areas such as network, security, or systems. • Experience with technology migrations, such as mergers or email and directory transitions. • Familiarity with enterprise data methodologies and platforms (e.g. Snowflake, Redshift, or Databricks) and relational databases (e.g. SQL Server, PostgreSQL, or MySQL). • K-12 or nonprofit experience, including familiarity with FERPA, NY Education Law 2-d, COPPA, and CIPA. • Familiarity with ITIL or similar practices for change, incident, and problem management. • Exposure to Q-SYS or similar AV control systems, such as Crestron or Extron. • Relevant certifications, such as Network+, Security+, CCNA, PCNSA, or cloud certifications. Physical Demands of Position This section describes the physical requirements that are necessary to successfully perform the essential responsibilities and functions of the position. Reasonable accommodations may be made to enable individuals with disabilities to perform these functions. • Ability to lift, carry, push, pull or position items up to 50 pounds. Benefits • We offer comprehensive benefits including: • Flexible Medical Health Plans, subsidizing the majority of costs for the employee, their spouse/domestic partner and children; • The ability to select between a variety of medical plans according to what best suits the employee's needs; • Dental and vision plans; • Disability benefits; • Life insurance; • Up to 12 weeks fully paid of Parental Leave; • Flexible spending account options; • Pre-tax commuter benefits (parking and transit); • Fitness and entertainment discounts; • A variety of support through our employee assistance program (EAP); • 403(b) retirement plan with employer match starting at 4% after one year, with increases tied to DREAM tenure; • Referral, performance, and tenure milestones bonuses; • Discounted school meals through our in-house Scratch Food Program; • Tuition reimbursement support (All FT Roles); • Access to a professional development fund (NEST Roles); • All full-time Network Support Team employees are eligible for approximately 48 days off throughout the year including holidays, sick days, personal days and summer Fridays. • Benefits are subject to change. Working Expectations • Able to travel between campuses in East Harlem and the South Bronx. • Able to work occasional after-hours for maintenance windows and incident response. • 5 days a week in person, with some optionality for one remote day per week based on operational need and manager pre-approval. Compensation DREAM offers a competitive salary commensurate with relevant experience. The incoming annual salary range for this position is $105,000 to $115,000 per year. New hires are typically brought into the organization at a salary closer to the start of the range depending on qualifications, internal equity, and the budgeted amount for the role. All regular employees receive annual compensation increases and have the opportunity to earn both performance- and tenure-based bonuses. Because we value tenure in each role, our salary ranges are not capped.