Senior Systems Administrator

DREAM•New York, NY

6d•$105,000 - $115,000•Hybrid

About The Position

DREAM is a youth-serving organization operating a network of PreK–12 charter schools and community programs in East Harlem and the South Bronx. 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. The role safeguards systems and student data, modernizes infrastructure management through automation and AI, and supports the organization through growth and technology transitions. The position calls for broad hands-on experience across networking, security, and systems, along with ownership, sound judgment, collaboration with partners and vendors, and continuous learning. The role also requires commitment to DREAM’s mission and values and the ability to work in person across campuses, with occasional after-hours work for maintenance windows and incident response.

Requirements

At least a high school diploma and 5+ years of IT and systems administration experience, or an associate degree or higher and 3+ years of IT and systems administration experience.
Hands-on experience with next-generation firewalls, VPN, switching, wireless, and multi-site networks.
Cybersecurity operations experience, including EDR, vulnerability management, incident response, and security monitoring through a SIEM.
Experience building and tuning monitoring and alerting for network and server health.
Strong identity administration experience with Active Directory, Google Workspace Admin, and an identity provider such as Okta, Entra ID, or JumpCloud.
Virtualization experience and practice with backup and disaster recovery.
Experience managing macOS and Windows endpoints through MDM platforms.
Experience automating administrative work with scripting languages such as PowerShell, Python, or Bash, and building automation or AI-assisted workflows that replace manual processes.
Database and cloud experience, including writing SQL and working with BigQuery in GCP.
Experience coaching or mentoring 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 technical and non-technical readers.
Ability to learn new tools quickly and adapt to changing priorities.
Strong belief in DREAM’s mission and values, including a desire to make a difference in the lives of students, families, and the community.
Ability to travel between campuses in East Harlem and the South Bronx.
Ability to work occasional after-hours for maintenance windows and incident response.
Ability to lift, carry, push, pull, or position items up to 50 pounds.

Nice To Haves

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 such as n8n or Zapier, and REST APIs.
Practical experience with additional cloud platforms such as AWS or Azure.
Background as an infrastructure lead with ownership of 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 such as Snowflake, Redshift, or Databricks, and relational databases such as 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 change, incident, and problem management practices.
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.

Responsibilities

Design, operate, and secure the multi-campus network, including firewalls, VPN, switching, and wireless.
Maintain cybersecurity, including endpoint detection and response (EDR), vulnerability and patch management, security monitoring, and incident response.
Maintain monitoring and alerting for network and system health, investigate outages, and prepare clear incident reports.
Administer Active Directory, Google Workspace, and Okta, including single sign-on (SSO) and provisioning.
Operate virtualization, servers, backup, and disaster recovery; manage macOS and Windows device fleets through mobile device management (MDM).
Administer Google Cloud Platform (GCP) environments, including BigQuery, and use SQL to support integrations, reporting, and automation.
Lead automation and AI projects from scoping through production.
Coach IT staff and resolve escalated support requests.
Plan sprints, manage vendors, document and communicate changes, and report status to leadership.
Travel between campuses in East Harlem and the South Bronx, and work occasional after-hours for maintenance windows and incident response.

Benefits

Medical plans with the employer subsidizing the majority of costs for employees and eligible family members.
Dental and vision plans.
Disability benefits.
Life insurance.
Up to 12 weeks of fully paid parental leave.
Flexible spending account options.
Pre-tax commuter benefits for parking and transit.
Fitness and entertainment discounts.
Employee assistance program (EAP) support.
403(b) retirement plan with an employer match starting at 4% after one year, with increases tied to DREAM tenure.
Referral, performance, and tenure milestone bonuses.
Discounted school meals through the in-house Scratch Food Program.
Tuition reimbursement support for all full-time roles.
Professional development fund access for NEST roles.
Approximately 48 days off throughout the year for full-time Network Support Team employees, including holidays, sick days, personal days, and summer Fridays.