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 every conversation because rigorous debate is how the strongest solutions get built. 
• Comfortable with uncertainty. The plan will change and the priorities will shift - you make smart calls with what you have and course-correct with good judgement when things evolve. 

QUALIFICATIONS:

• 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.

Preferred:

• 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

In accordance with the Illinois Pay Transparency Act, we’re providing the full salary range for this position. Actual compensation will be determined based on location, relevant experience and qualifications. Most offers will fall within a portion of the listed range. This position has a salary range of$80,000 - 110,000 annually, based on location, relevant experience and qualifications. In addition to base salary, we offer a comprehensive benefits package that includes:

• Paid holidays + PTO
• Company sponsored medical, dental, and vision insurance for you + your family
• FREE short-term and long-term disability insurance
• FREE $100k life insurance policy
• 401k plan with 4% company match + no vesting period
• $720 - $1,000 added to employee Health Savings Account annually for eligible health plans
• And more!