Head of Engineering

Head Of Engineering

We are hiring a Head of Engineering to own the craft, quality, and technical direction of a roughly 30-person engineering organization. This is deliberately not a role about growing headcount to 150. It is a role about making a small, senior team produce output that looks like a much larger one — by raising the engineering bar, tightening the systems that move real money, and being genuinely in the code and the architecture rather than adjacent to it.

You will lead through a mix of direct reports and a small group of engineering managers and tech leads, partnering closely with Product, Risk, and Compliance. You will spend your time on design reviews, incident retros, hiring, and the handful of technical bets that determine whether we can support the next order of magnitude of transaction volume.

If your ideal week is entirely calendar blocks and roadmap decks, this is not the right role. If your ideal week includes a hard design debate, a code review that changes someone's mind, and a coaching conversation that raises a manager's ceiling, keep reading.

• Set and own Rain's engineering quality bar across system design, code review, testing, observability, documentation, and technical decision-making, ensuring correctness is treated as critical for systems that move customer funds.

• Provide hands-on technical leadership by staying active in the codebase, reviewing critical PRs and designs, prototyping high-risk components, debugging production issues, and making key architectural and build-vs.
  
  -buy decisions.

• Own the technical architecture and strategy across card issuing, wallets, ledger, money movement, onchain settlement, and integrations with card networks and banking partners.

• Drive reliability, scalability, and operational excellence by establishing SLOs, improving incident response, capacity planning for 10x growth, and designing resilient systems with graceful degradation, idempotency, and replay capabilities.

• Build security, compliance, and correctness into the platform by design, partnering closely with Risk, Compliance, and Security to meet PCI, SOC 2, fraud-control, regulatory, and blockchain infrastructure requirements.

• Increase engineering velocity without sacrificing quality through improvements to CI/CD, developer tooling, local environments, technical debt management, and architecture that enables teams to ship safely and independently.

• Build and develop a high-performing engineering organization by coaching engineering managers and technical leads, maintaining a high hiring and performance bar, establishing clear team ownership, and partnering effectively across Product, Design, Risk, Compliance, and GTM.

• 10+ years building production software, including 4+ years leading engineers — ideally as a Head of Engineering, Director, or Senior EM at a company where the systems handled real consequences.

• Currently and demonstrably hands-on. You have written or reviewed meaningful production code within the last year and you want a role where that continues.

• Deep experience with distributed backend systems at scale: data modeling, consistency and idempotency, queues and event-driven design, and the operational reality of running all of it.

• A track record of raising an engineering bar. You can point to specific practices you introduced and the measurable change in quality, velocity, or reliability that followed.

• Real reliability ownership — you have carried a pager, run incident command during a serious outage, and built the follow-through that kept it from recurring.

• Experience in payments, fintech, banking infrastructure, or another domain where money, ledgers, or regulatory obligations made correctness non-negotiable.

• Strong hiring and coaching instincts, with managers or senior engineers you have developed who would work for you again.

• Clear written communication. You can make a complex technical tradeoff legible to a CEO, a compliance officer, and a partner's engineering team in the same week.

• Comfort with ambiguity and speed. You would rather ship something correct this quarter than design something perfect for next year.