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Cloudflare is seeking a Senior Director of Engineering to lead the engineering organization responsible for its billing platform and quote-to-cash systems. This is a manager-of-managers role overseeing multiple engineering teams responsible for usage-based billing, subscriptions, invoicing, payments, entitlements, tax, revenue data, customer account lifecycle, and financial reconciliation.
Key responsibilities include owning the multi-year engineering strategy and execution roadmap for the billing platform; leading and developing a distributed organization of engineering managers and senior technical leaders; building the next layer of leadership through coaching and mentorship; driving platform architecture improvements in correctness, scalability, reliability, and auditability; and building systems that support complex billing motions including usage-based pricing, enterprise contracts, self-serve purchasing, partner and reseller channels, and customer lifecycle management.
You will strengthen financial data integrity across billing, payments, revenue recognition, ERP, CRM, data warehouse, tax, and reporting systems. You'll improve reconciliation, observability, alerting, SLOs, and incident response for billing-critical services. Cross-functional partnership is essential—you'll work closely with Product, Finance, Revenue Operations, Accounting, Tax, Legal, Sales, and Support to translate business requirements into durable engineering systems. You'll make pragmatic build/buy/integrate decisions across the billing and payments ecosystem and represent billing engineering in executive forums with clear tradeoffs and investment recommendations.
The ideal candidate has 15+ years of software engineering experience, including 7+ years leading engineering teams and 3+ years directly managing engineering managers. Experience leading billing, payments, fintech, financial platforms, commerce platforms, or quote-to-cash systems is highly desirable. Strong technical judgment in distributed systems, SaaS platforms, service-oriented architectures, APIs, data pipelines, and cloud-native infrastructure is required. You should have a proven ability to define and execute multi-year platform strategies across multiple teams and executive stakeholders.
