Software Engineer II (Remote)

Posted Yesterday
Hiring Remotely in Chicago, IL, USA
In-Office or Remote
87K-111K Annually
Junior
Fintech
Inspira Financial's innovative financial wellness solutions help people plan, save, and invest.
The Role
Supports the reliability and operational excellence of health benefits systems involving HSA administration, banking integrations, compliance, and money movement. Responsibilities include independently resolving escalations, monitoring dashboards and logs, triaging incidents, executing data corrections, maintaining runbooks, analyzing recurring support issues, and collaborating with engineering, product, treasury, and operations teams. The role also mentors teammates, contributes to postmortems, improves troubleshooting processes, and uses AI tools for prototyping and debugging.
Summary Generated by Built In
Join Us!
Take the next step in your journey at Inspira Financial. Guided by our mission to enable better health and greater wealth, we help businesses and individuals thrive today, tomorrow, and into retirement by strengthening and simplifying the health and wealth journey.
Serving more than 7 million clients and representing over $62 billion in assets, Inspira partners with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners to help the people they support plan, save, and invest for a brighter future. Through solutions including automatic rollover services, health savings accounts, emergency savings, and custody services, Inspira is focused on delivering better outcomes for all. Learn more at inspirafinancial.com .
Our values shape how we show up every day. We Lead with Heart by acting with compassion, empathy, and doing what's right; Cultivate Trust through integrity, transparency, and accountability; Aim Higher by never settling for what's expected and continually raising the standard; and Win Together by collaborating inclusively to achieve the best outcomes.
Our growth and culture haven't gone unnoticed -- we've been recognized on Crain's Fast 50 and Inc. 5000 for remarkable growth, and named to Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer for our workplace culture and benefits.
Don't meet every single requirement? That's okay. We know growth comes from people who are willing to learn and challenge themselves, not just check every box. If you're energized and inspired by meaningful work, continuous development, and being part of a team that turns collective effort into real impact, we want to hear from you. We look forward to receiving your application.
Remote status and role locations are subject to change, and relocation is not provided.
Job Summary & Responsibilities
Software Engineer II willplay 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:

o Support Engineering and Operations
  • 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

o System Monitoring and Incident Triage
  • 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

o 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
  • 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
$87,100-$111,000 per year

Skills Required

  • 2+ years of experience in software engineering or support engineering roles
  • Strong analytical and problem-solving skills
  • Practical experience using AI tools such as Claude Code, GitHub Copilot, or ChatGPT for prototyping, debugging, and problem-solving
  • Bachelor's degree in computer science or equivalent experience
  • Working understanding of JavaScript
  • Working understanding of TypeScript and React
  • Working understanding of Git version control
  • Working understanding of databases such as PostgreSQL
  • Working understanding of cloud platforms such as GCP
  • Excellent communication and teamwork skills
  • Strong attention to detail and organizational skills
  • Willingness to learn and adapt in a fast-paced environment
  • Familiarity with observability tools such as Datadog
  • Understanding of GraphQL
  • Experience writing and maintaining technical documentation
  • Experience with banking or payment APIs such as Plaid
  • Experience with Google BigQuery or similar data warehousing tools
  • Strong sense of ownership and follow-through
  • Prior customer support or technical troubleshooting experience
  • Ability to occasionally work overtime or after hours

What the Team is Saying

Hugh
Rachel Nielsen
Albert
Rebecca Karnoscak
Lauren Schulz
Oliver Siafa

Inspira Financial Compensation & Benefits Highlights

  • Leave & Time Off Breadth The package advertises substantial PTO, 10 paid holidays, and dedicated volunteer time off, alongside paid parental leave. These provisions indicate broad time-away support across multiple leave types.
  • Retirement Support A 401(k) with a “generous” employer match is highlighted, with tax-advantaged accounts (HSAs/FSAs) administered in-house to simplify savings. This combination supports longer-term financial security and ease of use.
  • Wellbeing & Lifestyle Benefits Offerings include a mindfulness/meditation app subscription, pet insurance, and other lifestyle perks. These additions round out the core benefits with everyday wellbeing support.

Inspira Financial Insights

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The Company
HQ: Oak Brook, IL
1,805 Employees
Year Founded: 2000

What We Do

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.

Why Work With Us

Inspira Financial is a leading financial services company offering specialized financial wellness solutions to employers, institutions, advisors, and individuals.

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Inspira Financial Offices

Remote Workspace

Employees work remotely.

Typical time on-site: None
HQOak Brook, IL
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Longwood, FL
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