Head of Engineering

Rain•New York, NY

5d•$300,000 - $400,000•Hybrid

About The Position

Rain is seeking a Head of Engineering to lead a roughly 30-person engineering organization, focusing on enhancing the craft, quality, and technical direction. This role emphasizes making a small, senior team highly productive by elevating the engineering bar, strengthening systems that handle real money, and maintaining hands-on involvement in code and architecture. The Head of Engineering will lead through direct reports, engineering managers, and tech leads, collaborating closely with Product, Risk, and Compliance. Responsibilities include design reviews, incident retrospectives, hiring, and making key technical decisions to support significant growth in transaction volume. This is not a role for those who prefer solely strategic planning; it requires active engagement in technical debates, code reviews, and coaching.

Requirements

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.

Nice To Haves

Hands-on experience with card issuing, processing, or the Visa and Mastercard network stack.
Working knowledge of stablecoins, onchain settlement, custody and key management, or EVM and Solana infrastructure.
Experience operating under SOC 2, PCI DSS, or bank and program-manager oversight.
Experience leading distributed or multi-region teams.

Responsibilities

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.

Benefits

Unlimited time off (minimum 10 days required)
Flexible working (work from home, office, or both)
Home office setup stipend
95% coverage of health, dental, and vision plan costs for US employees
90% coverage of health, dental, and vision plan costs for dependents
100% company-subsidized life insurance plan
401(k) with a 4% company match
Equity option plan
Monthly stipend for health and wellness spending (gym memberships, fitness classes, massages, etc.)
In-office meals (lunch and dinner covered with DoorDash credit for those working in the office)
Team summits (team and company offsites, domestic and international)