[Hiring] Lead Software Engineer @Rocky Mountain Reserve

Role Description

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.

What You'll Do

• 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

Qualifications

• 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

Requirements

• 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)

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
• Comprehensive health benefits
• FSA & HSA Accounts
• 401(k) with employer match
• Generous PTO that increases with tenure