Lead Software Engineer

Lead Software Engineer Rocky Mountain Reserve | Remote | Full-Time About Rocky Mountain Reserve Rocky Mountain Reserve is a benefits administration company specializing in HSAs, FSAs, HRAs, and other consumer-directed benefit accounts. We help employers and employees get the most out of their benefits through great service and great technology. We're investing heavily in our engineering capabilities and are looking for a technical leader to help us build faster and smarter. About the Role 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 What We're Looking For Required: 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 Strongly Preferred: 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) What Success Looks Like Within 3 months: You're shipping meaningful features and have assessed our team's current workflows and tooling Within 6 months: The team has adopted AI-assisted development practices you've established, with measurable improvements in velocity — without sacrificing quality or compliance posture Within 12 months: You've built a development culture that moves fast, ships confidently, and serves as a model for how a regulated-industry engineering team can leverage AI Compensation & Benefits Competitive Total Salary & Bonus Compensation: $175,000 – $225,000 Performance Bonus Eligible based on company and individual performance. RMR is a privately held company with no debt or outside investors. We don’t offer equity because we aren’t looking for the boom and bust of the VC world nor are we interested in going public or taking PE money. We are a profitable, stable company and rather than lottery ticket RSUs we pay fair base salaries with generous performance bonuses so that when the company makes money so do you. 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 Rocky Mountain Reserve is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.