Senior Director of Engineering, Billing Platform

About Us At Cloudflare, we are on a mission to help build a better Internet. Today the company runs one of the world’s largest networks that powers millions of websites and other Internet properties for customers ranging from individual bloggers to SMBs to Fortune 500 companies. Cloudflare protects and accelerates any Internet application online without adding hardware, installing software, or changing a line of code. Internet properties powered by Cloudflare all have web traffic routed through its intelligent global network, which gets smarter with every request. As a result, they see significant improvement in performance and a decrease in spam and other attacks. Cloudflare was named to Entrepreneur Magazine’s Top Company Cultures list and ranked among the World’s Most Innovative Companies by Fast Company. At Cloudflare, we’re not looking for people who wait for a polished roadmap; we’re looking for the builders who see the cracks in the Internet that everyone else has simply learned to live with. We value candidates who have the instinct to spot a "normalized" problem and the AI-native curiosity to create a solution using the latest tools. Our culture is built on iteration, leveraging AI to ship faster today to make it better tomorrow, while ensuring that every improvement, no matter how small, is shared across the team to lift everyone up. If you’re the type of person who values curiosity over bureaucracy, and that AI is a partner in solving tough problems to keep the Internet moving forward, you’ll fit right in. Locations: Austin, London, Lisbon, SF, NYC, and Seattle About the Role Cloudflare's billing platform is a critical part of how customers buy, adopt, and expand across Cloudflare's products. It sits at the intersection of product monetization, customer experience, financial correctness, revenue operations, and enterprise trust. We are hiring a Senior Director, Engineering to lead the engineering organization responsible for Cloudflare's billing platform and adjacent quote-to-cash systems. This leader will own the technical strategy, organizational design, execution model, and operational health of the systems that support usage-based billing, subscriptions, invoicing, payments, entitlements, tax, revenue data, customer account lifecycle, and financial reconciliation. This is a senior director-level role for someone who has led managers before and can scale a multi-team platform organization where correctness, reliability, auditability, and customer trust are mandatory. The right leader will combine strong engineering judgment, manager-of-managers leadership, and executive-level partnership across Product, Finance, Revenue Operations, Legal, Sales, Support, and external platform vendors. What You'll Do • Own the multi-year engineering strategy, investment plan, and execution roadmap for Cloudflare's billing platform and quote-to-cash integrations. • Lead and develop a distributed organization of engineering managers, senior technical leaders, and product engineering teams. • Build the next layer of leadership by coaching managers, strengthening technical leadership, and improving planning, accountability, and execution predictability. • Drive platform architecture that improves correctness, scalability, reliability, auditability, and speed of product launch. • Build systems that support usage-based billing, subscriptions, enterprise contracts, self-serve purchasing, partner and reseller motions, invoicing, payments, credits, refunds, adjustments, entitlements, tax, and customer lifecycle changes. • Strengthen financial data integrity across billing, payments, revenue recognition, ERP, CRM, data warehouse, tax, and reporting systems. • Improve reconciliation, observability, alerting, SLOs, incident response, and operational controls for billing-critical services. • Partner with Product, Finance, Revenue Operations, Accounting, Tax, Legal, Sales, and Support to turn ambiguous business requirements into durable engineering systems. • Make pragmatic build, buy, and integrate decisions across billing, payment processing, tax, ERP, CRM, entitlement, and revenue platforms. • Represent billing engineering in executive forums with clear tradeoffs, delivery status, risks, and investment recommendations. Desirable Skills, Knowledge, and Experience • 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, quote-to-cash systems, or other systems where correctness and auditability are mandatory. • Strong technical judgment in distributed systems, SaaS platforms, service-oriented architectures, APIs, data pipelines, and cloud-native infrastructure. • Proven ability to define and execute a multi-year platform strategy across multiple teams, business functions, and executive stakeholders. • Experience with usage-based billing, subscription billing, metering, invoicing, payments, credits, refunds, disputes, taxation, entitlement management, revenue data, or reconciliation. • Familiarity with platforms such as Stripe or other payment processors, Salesforce or other CRM systems, ERP systems, tax engines, revenue recognition systems, data warehouses, and BI/reporting tools. • Track record improving operational excellence for critical systems through SLOs, observability, incident response, change control, migrations, reconciliation, and customer-impact reduction. • Ability to translate complex technical, financial, and organizational tradeoffs into clear decisions for executive, finance, product, and engineering audiences. • Experience recruiting, coaching, and retaining strong engineering managers and senior technical leaders. • High standards for engineering quality, accountability, documentation, customer empathy, and cross-functional follow-through. • Practical AI fluen