Software Engineer II (Remote)

Join Us!
Take the next step in your journey at Inspira Financial. You will help businesses and individuals thrive today, tomorrow, and into retirement. Become part of a company that is people centric and client obsessed in every interaction; a community of forward-thinking individuals focused on driving results to deliver our mission with an unwavering commitment to integrity. Join us as we strengthen and simplify the health and wealth journey -- relentlessly pursuing better outcomes for all. We believe in finding the best talent! While some roles are based at one of our office locations, remote roles can sit in any of the following states: AL, AZ, FL, GA, IA, IL, IN, MI, MN, MO, NC, NE, PA, SC, TN, TX, UT, VA and WV. Remote status and role locations are subject to change. Relocation is not provided.
Employees within a 90-minute radius of our Oak Brook, IL headquarters are required to adhere to the company in-office work guidelines of 4 days per month minimum from 10 am to 2 pm (1 of the 4 days must be a Monday or Friday).
This requirement does not apply to support specialist positions.
Don't meet every single requirement? Here at Inspira Financial, we believe there is no "perfect" candidate and want to encourage applying even if all the requirements listed aren't met. Our goal is to build an authentic workplace by valuing diversity in our candidates. We work to ensure that our team reflects the diversity of the businesses and clients we serve. We are always looking to expand our growing team with dynamic and enthusiastic individuals. If you enjoy a collaborative, fun environment that champions career development, Inspira Financial is the place for you! We look forward to receiving your application! Check out this Inspira Financial video to learn more about our company!
Inspira Financial provides health, wealth, retirement, and benefits solutions that strengthen and simplify the health and wealth journey. With more than 7 million clients, representing over $62 billion in assets, Inspira works with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners -- helping the people they care about plan, save, and invest for a brighter future. Inspira relentlessly pursues better outcomes for all with our automatic rollover services, health savings accounts, emergency savings funds, custody services, and more. Learn more at inspirafinancial.com .
We have been recognized for our remarkable growth on lists such as Crain's Fast 50 and Inc. 5000, and for our outstanding workplace culture and benefits with Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer awards.
Job Summary & Responsibilities
We are seeking a talented Support Software Engineer II to join our growing team. Our engineering team plays a critical role in ensuring the reliability and efficiency of our systems, which in turn drives customer delight. The Support Engineer role will help us maintain operational excellence.
This role is an excellent opportunity for someone looking to gain hands-on technical experience while working across multiple teams. You 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. You'll work directly with production data involving real money movement, tax reporting, and multi-bank operations.
At First Dollar, we believe in empowering engineers to build a smarter health benefits platform - one where human expertise is amplified, not replaced, by AI tools. We seek engineers who have demonstrated experience using AI responsibly to accelerate their development workflow, improve code quality, and solve complex problems more efficiently.
O ur engineering team is built on the principles of humans over code. We are a tight-knit group of lifelong learners in a constant quest to be a team that is greater than the sum of its parts. Come join us!

• Duties & Responsibilities:

• Support Engineering and Operations

• Ability to independently handle escalations end-to-end without manager intervention

• Demonstrated judgement on when to escalate vs. r esolve, 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

• System Monitoring and Incident Triage

• Monitor operational dashboards, error logs, and alerting systems to ensure system health and performance and ad d ress 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

• Cross-Team Collaboration and Learning

• 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

Preferred Qualifications
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

• Node.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

Compensation & Benefits
$91,000-$111,000 per year