Systems Administrator I New Chicago, IL

Hopscotch Healthcare, Inc.; Chicago, Northern (IL, KY); Hybrid; USD 85,000 - 110,000; Full time

Job summary

Hopscotch Primary Care is seeking a Systems Administrator to ensure reliable IT platforms across corporate and clinic environments. You will lead end-to-end projects, optimize healthcare IT operations, and drive improvements that enhance service quality for patients and clinicians.

The role emphasizes cloud and SaaS administration, IAM governance, security compliance, and proactive automation. You will collaborate with teams to maintain scalable, secure infrastructure as the company grows.

Qualifications

• Experience administering IT systems across corporate and clinic environments.
• Experience with cloud platforms and SaaS administration.
• Strong IAM administration and security/compliance focus.
• Ability to lead end-to-end projects.

Responsibilities

• Own and support lifecycle of core IT systems across environments.
• Manage hardware/software lifecycle, endpoints, and servers.
• Administer cloud platforms and SaaS, including licensing.
• IAM administration and access governance.
• Ensure security, compliance, reliability, and performance.
• Drive automation and internal tooling.
• Develop IT standards and policies.
• Support disaster recovery and business continuity.
• Provide high-quality technical support and incident escalation.
• Act as escalation point for complex issues.

Skills

Systems administration

IAM administration

Cloud platforms

Automation & scripting

Security & compliance

Technical support

Stakeholder communication

Tools

Azure

Foundry pipelines

IAM tooling

Server management tools

Job description

At Hopscotch Primary Care, we believe great healthcare should be accessible to all people across all communities. Today, almost 20% of Americans live in a rural community, yet only 11% of physicians practice in those same communities. We are on a mission to transform healthcare in rural America. We provide high-quality primary care tailored to meet the needs of our patients through our robust care model and comprehensive care team, delivering care in our clinics, and across settings, and wrapping resources around the patients who need them most.

Our patients and the care teams who serve them sit at the center of everything we do at Hopscotch. Hopscotch Primary Care takes a team approach to serve patient needs and provide the best care possible. Our goal is to provide the care each of us would want for ourselves or for our family members, in the right setting, and at the right time.

Today, we are serving thousands of patients in our value-based care model and the number is growing every day. If you want to bring your experience, skill and passion to make a lasting impact in healthcare, we’d like to meet you.

About the role

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.

Responsibilities

Near-term focus areas for this role will include, but are not limited to:

• 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.

About you

• Business-oriented with the ability to articulate business needs, scope solutions and clearly communicate value and timing of work.
• Data-informed and decisive - confident making prioritization decisions using a mix of qualitative insights, quantitative data, KPIs and expected business impact.
• A clear and compelling communicator ; able to articulate the strategy and value of the tactical roadmap items to audiences ranging from technical peers to executive leadership.
• Self-aware and resilient , able to recognize missteps, learn from execution failures and re‑engage with confidence and a bias toward action.
• From a cultural perspective, you are:
• Accountable . You hold a high standard and you expect it from others too.
• Someone who treats mistakes as data. You move fast, name what isn't working, fix it, and carry the lesson forward.
• Customer-obsessed. You build genuine empathy with users, dig into what they actually need, and stay focused on solving real problems.
• A problem-solver, not a finger-pointer. You own challenges alongside your teammates - no blame, no deflection, just shared accountability for finding the way forward.
• A contributor who shapes the answer. You bring your strengths and perspective to