Entry Level Linux Devops Engineer Jobs in Chicago, IL

Software Engineer II will play a critical role in ensuring the reliability and efficiency of our systems, which in turn drives customer delight. The Support Engineer role will help Inspira maintain operational excellence.

This role is an excellent opportunity for someone looking to gain hands-on technical experience while working across multiple teams, and will be at the intersection of engineering, operations, and customer success, helping to diagnose issues, triage requests, execute data corrections, and ensure our systems run smoothly.

This role supports critical health benefits infrastructure such as HSA administration, banking integrations, and regulatory compliance. Support Software Engineer II work directly with production data involving real money movement, tax reporting, and multi-bank operations.

• Duties & Responsibilities:

• Ability to independently handle escalations end-to-end without manager intervention
• Demonstrated judgement on when to escalate vs. resolve, especially around money movement and compliance-sensitive issues
• Track record of identifying recurring support patterns and proposing systemic improvements
• Coach and mentor less experienced teammates on troubleshooting approaches and best practices
• Respond to internal support requests from various teams and assist in troubleshooting and fixing technical issues such as executing data corrections, processing trustee-to-trustee transfers and settlements, and overseeing money movement and remediation efforts
• Identify and route unresolved issues to the appropriate engineering or product teams for further action
• Leverage AI as a tool, not a replacement - Candidates are expected to understand that AI is a power productivity multiplier while maintaining engineering judgment, and ensuring AI generated code meets quality standards

• Monitor operational dashboards, error logs, and alerting systems to ensure system health and performance and address ongoing technical issues
• Identify and escalate any anomalies or critical system alerts that require immediate attention
• Monitor error reports, and logs and operational dashboards to help diagnose and address ongoing technical issues
• Ensure that critical alerts and operational failures are addressed by the relevant teams

• Act as a liaison between engineering support and delivery teams, translating support trends into actionable requirements
• Ownership of runbook creation and maintenance, not just consumption
• Contribute to incident postmortems and driving follow-up action items
• Partner with engineering, product, treasury and operations teams to refine internal troubleshooting processes
• Continuously develop a deeper understanding of internal systems and tools such as HSA regulations, banking integrations, and investments
• Document troubleshooting procedures findings and contribute to knowledge-sharing efforts
• Identify patterns in support requests that could inform product or engineering improvements
• Actively participate in team discussions and process improvements
  • Other duties as assigned

Education & Experience:

• 2+ years of experience in software engineering or support engineering roles
• Strong analytical and problem-solving skills
• Practical AI experience required - Comfortable using tools such as Claude Code, GitHub Copilot, ChatGPT for prototyping, debugging, and problem-solving
• Bachelor's degree in computer science or equivalent experience

Technical Proficiency and Skills:

Required Skills:

Working understanding of

• js
• TypeScript and React
• Git Version Control System
• Database (e.g. Postgres SQL)
• Cloud Platform (e.g. GCP)
• Excellent communication and teamwork skills
• Great attention to detail and organizational skills
• Willingness to learn and adapt in a fast-paced environment

Preferred Skills:

• Familiarity with observability tools (Data Dog or similar)
• Understanding of GraphQL
• Experience with writing and maintaining technical documentation
• Experience with banking/payment APIs such as Plaid (or similar)
• Experience with Google BigQuery or similar data warehousing tool
• Strong sense of ownership and follow-through
• Prior experience in a customer support or technical troubleshooting role

Other Requirements:

• Infrequent travel (10%)
• Ability to occasionally work overtime or after hours
• Prolonged periods of sitting at a desk and working on a computer