VP of Engineering

Rain•New York, NY

7d•$320,000 - $450,000•Hybrid

About The Position

Rain is seeking a VP of Engineering to lead its roughly 50-person engineering organization. This role focuses on enhancing the quality and technical direction of a senior team to achieve output comparable to a much larger organization. The ideal candidate will improve engineering standards, strengthen systems for handling real money, and be actively involved in code and architecture. The role involves leading through direct reports, engineering managers, and tech leads, collaborating with Product, Risk, and Compliance. Responsibilities include design reviews, incident retrospectives, hiring, and making key technical decisions to support future growth in transaction volume. This is a hands-on role for someone who thrives on technical debates, code reviews, and coaching, rather than solely focusing on calendar blocks and roadmap decks.

Requirements

15+ years building production software, including 8+ years leading engineers and meaningful time leading managers.
Current technical credibility; have written or reviewed meaningful production code recently enough to add value in architecture reviews.
Deep experience with distributed backend systems at scale: data modeling, consistency and idempotency, queues and event-driven design, and operational realities.
A track record of raising an engineering bar, with specific examples of introduced practices and their measurable impact on quality, velocity, or reliability.
Real reliability ownership: experience carrying a pager, running incident command during serious outages, and implementing follow-through to prevent recurrence.
Experience in payments, fintech, banking infrastructure, or a domain where correctness is non-negotiable due to money, ledgers, or regulatory obligations.
Experience hiring and developing engineering managers, with leaders who would work for you again.
Clear written communication skills, able to explain complex technical tradeoffs to diverse audiences (CEO, compliance officer, partner's engineering team).
Executive range: comfortable in board or partner conversations as well as design reviews, able to hold technical positions under commercial pressure.
Comfort with ambiguity and speed; preference for shipping correct solutions quickly over designing perfect long-term solutions.

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

Own engineering strategy and architecture across card issuing, wallets, ledger, money movement, onchain settlement, and integrations with card networks and banking partners — including the multi-year technical roadmap.
Set and own Rain's engineering quality bar across system design, code review, testing, observability, documentation, and technical decision-making, ensuring correctness for systems that move customer funds.
Review critical designs, weigh in on high-consequence architecture and build-vs.-buy decisions, and ensure technical understanding to prevent flawed designs.
Drive reliability, scalability, and operational excellence by establishing SLOs, improving incident response, capacity planning for 10x growth, and designing resilient systems.
Build security, compliance, and correctness into the platform by design, partnering with Risk, Compliance, and Security to meet PCI, SOC 2, fraud-control, regulatory, and blockchain infrastructure requirements.
Increase engineering velocity through improvements to CI/CD, developer tooling, local environments, technical debt management, and architecture that enables independent team shipping.
Build and develop a high-performing engineering organization by hiring and coaching engineering managers and technical leads, establishing clear team ownership, and owning headcount planning and performance.
Operate as a member of the leadership team — translating company strategy into technical plans, partnering across Product, Design, Risk, Compliance, and GTM, and representing engineering to the board, partners, and customers.

Benefits

Unlimited time off (minimum 10 days required)
Flexible working (work from home, office, or both)
Home office setup stipend
Health, dental, and vision plan costs covered at 95% for employees and 90% for dependents (US)
100% company-subsidized life insurance plan (US)
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 (company and team offsites, domestic and international)