Systems Administrator I

Hopscotch Primary Care•Chicago, IL

11d

About The Position

We are looking for a Systems Administrator to join our team at a critical and exciting time for the company. In this role, you will be responsible for ensuring that Hopscotch’s core IT platforms are reliable, well-operated, and continuously improving as the organization scales. You will be trusted to operate independently, lead projects end-to-end, and proactively identify improvements that strengthen clinical operations, service quality, and IT system experience.

Requirements

2+ years of IT / Helpdesk / system administration experience
Bachelor’s degree (computer science, engineering or technical discipline)
A degree is not required; we heavily encourage you to apply regardless of college experience.
Experience in maintaining troubleshooting a wide variety of systems and networks.

Nice To Haves

Experience with Identity & Endpoint management for both Mac and Windows.
Experience with Network management and tooling (e.g., VLAN/WLAN)
Experience with cybersecurity principles (CIA)
Experience with AI tooling such as Claude (Code), ChatGPT (Codex), and/or similar tools.
Comp TIA
Network+ Certification
Security + Certification

Responsibilities

Own and support the full lifecycle of core IT systems used across corporate and clinic environments.
Lifecycle management of all hardware and software.
Endpoint and server management, configuration, and support.
Cloud platform and SaaS administration, including licensing and access governance.
Identity & Access Management (IAM) administration and support across systems.
Ensure systems are configured to meet security, compliance, and operational standards.
Ensure the reliability, scalability, and performance of IT infrastructure through proactive improvement and automation.
Monitor and improve service quality across IT systems and networks using defined metrics (e.g., Availability, performance, incident trends, etc).
Identify recurring operational issues and drive corrective actions within assigned systems, through change management and improvements.
Drive infrastructure efficiency and performance within assigned systems, including design, implementation, and ongoing iteration.
Design and build internal tools and automations to solve operational needs (e.g., AI agents, Foundry pipelines, Azure Playbooks).
Maintain clear, consistent, and well-documented IT standards that support scale, security, and operational reality.
Contribute to the creation, review, and implementation of IT policies and procedures.
Support disaster recovery and business continuity planning, testing, and implementation.
Ensure system changes are implemented thoughtfully and consistently to reduce variance, risk, and configuration drift.
Provide high-quality technical support while continuously improving service delivery and user experience.
Serve as the escalation point for complex or high-impact technical issues.
Own the quality, accuracy, and usefulness of IT ticket data.
Use operational signals (ticket trends, response times, failure patterns) to inform prioritization and drive improvements.
Propose and implement improvements to support workflows based on measured impact and feedback.