Lead Software Engineer
About The Position
We're looking for a Lead Software Engineer who represents the best of both worlds: someone who has fully embraced AI-assisted development tools (Claude Code, Cursor, Copilot, and similar) to ship software at a pace that wasn’t possible a few years ago — and someone with the engineering depth to know exactly where those tools fall short. You know the difference between moving fast and "vibe coding." You understand that AI-generated code still needs architecture, testing, security review, and thoughtful design — especially in a regulated industry handling sensitive health and financial data. And you're excited to teach others how to work this way. This is a hands-on leadership role. You'll write code, set technical direction, and mentor our existing development team as they adopt AI-assisted workflows.
Requirements
- 7+ years of professional software engineering experience, with at least 2 years in a lead or senior role
- Demonstrated, hands-on fluency with AI coding tools (Claude Code, Cursor, Copilot, or similar) in real production work — not just experimentation
- Strong software engineering fundamentals: system design, testing strategy, code review, and debugging skills that let you catch what AI tools miss
- Experience mentoring engineers and raising the technical bar of a team
- Experience building and operating production systems that handle sensitive data
Nice To Haves
- Experience in benefits, payroll, fintech, or HR tech — companies like Rippling, Gusto, Justworks, Lively, HealthEquity, or similar
- Working knowledge of HIPAA compliance and SOC 2 audit processes from an engineering perspective
- Experience integrating with financial systems (banking rails, custodial accounts, payment processing)
- Familiarity with the consumer-directed benefits space (HSA/FSA/HRA/COBRA administration)
Responsibilities
- Design, build, and ship features across our benefits administration platform using modern, AI-accelerated development workflows
- Establish best practices for AI-assisted development: when to lean on the tools, when to slow down, and how to review and validate generated code
- Mentor and upskill our existing engineering team in using tools like Claude Code effectively and responsibly
- Own architectural decisions and ensure our systems remain maintainable, secure, and scalable as development velocity increases
- Champion engineering rigor — testing, code review, documentation, and observability — in an AI-augmented workflow
- Help ensure our systems and processes meet HIPAA and SOC 2 requirements, working alongside our compliance team
- Contribute to hiring and team growth as we scale
Benefits
- Competitive Total Salary & Bonus Compensation: $175,000 – $225,000
- Performance Bonus Eligible based on company and individual performance.
- Guaranteed Remote: RMR is a remote first company. Our team is spread across the country so you can live where you want provided it’s a US state we can employ you in.
- Comprehensive health benefits
- FSA & HSA Accounts
- 401(k) with employer match
- Generous PTO that increases with tenure
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
