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 fluency: uses AI tools to accelerate engineering work, improve operating leverage, and raise the team's quality bar without weakening ownership or judgment. Bonus Points • Experience modernizing or replacing legacy billing, payments, ERP, CRM, tax, entitlement, or revenue systems in a public company or high-growth SaaS business. • Experience supporting enterprise contracts, reseller or partner billing, marketplace billing, multi-currency billing, global taxation, or public-sector billing requirements. • Experience with internet-scale SaaS, developer platforms, cloud infrastructure, security products, or consumption-based monetization. • Experience building platforms that support product-led growth and enterprise sales motions at the same time. • Experience leading financial-systems organizations through scale, transformation, and cross-functional operating model changes. • Experience with financial controls, SOC 2, PCI, privacy, fraud prevention, audit support, or regulated financial workflows. • Experience leading large data migrations or phased platform transformations without interrupting revenue operations or customer billing. • Strong product sense around pricing flexibility, customer transparency, billing explainability, and self-service administration. Compensation Compensation may be adjusted depending on work location. • For Seattle/NYC/California based hires - Estimated annual salary of: $273,000 - $341,000 • For SF/Bay Area based hires - Estimated annual salary of: $286,000 - $258,000 • For Lisbon based hires - Estimated annual salary of: €146,000 - €183,000 Equity This role is eligible to participate in Cloudflare’s equity plan. Benefits Cloudflare offers a complete package of benefits and programs to support you and your family. Our benefits programs can help you pay health care expenses, support caregiving, build capital for the future and make life a little easier and fun! The below is a description of our benefits for employees in the United States, and benefits may vary for employees based outside the U.S. Health & Welfare Benefits • Medical/Rx Insurance • Dental Insurance • Vision Insurance • Flexible Spending Accounts • Commuter Spending Accounts • Fertility & Family Forming Benefits • On-demand mental health support and Employee Assistance Program • Global Travel Medical Insurance Financial Benefits • Short and Long Term Disability Insurance • Life & Accident Insurance • 401(k) Retirement Savings Plan • Employee Stock Participation Plan Time Off • Flexible paid time off covering vacation and sick leave • Leave programs, including parental, pregnancy health, medical, and bereavement leave What Makes Cloudflare Special? We’re not just a highly ambitious, large-scale technology company. We’re a highly ambitious, large-scale technology company with a soul. Fundamental to our mission to help build a better Internet is protecting the free and open Internet. Project Galileo: Since 2014, we've equipped more than 2,400 journalism and civil society organizations in 111 countries with powerful tools to defend themselves against attacks that would otherwise censor their work, technology already used by Cloudflare’s enterprise customers--at no cost. Athenian Project: In 2017, we created the Athenian Project to ensure that state and local governments have the highest level of protection and reliability for free, so that their constituents have access to election information and voter registration. Since the project, we've provided services to more than 425 local government election websites in 33 states. 1.1.1.1: We released 1.1.1.1 to help fix the foundation of the Internet by building a faster, more secure and privacy-centric public DNS resolver. This is available publicly for everyone to use - it is the first consumer-focused service Cloudflare has ever released. Here’s the deal - we don’t store client IP addresses never, ever. We will continue to abide by our privacy commitment and ensure that no user data is sold to advertisers or used to target consumers. Sound like something you’d like to be a part of? We’d love to hear from you! Please note that applicants who progress to the offer stage of the interview process may be asked to attend an in-person interview within one of the Cloudflare Offices or Cloudflare Hubs. More details about this will be available at that stage of the interview process. This position may require access to information protected under U.S. export control laws, including the U.S. Export Administration Regulations. Please note that any offer of employment may be conditioned on your authorization to receive software or technology controlled under these U.S. export laws without sponsorship for an export license. Cloudflare is proud to be an equal opportunity employer. We are committed to providing equal employment opportunity for all people and place great value in both diversity and inclusiveness. All qualified applicants will be considered for employment without regard to their, or any other person's, perceived or actual race, color, religion, sex, gender, gender identity, gender expression, sexual orientation, national origin, ancestry, citizenship, age, physical or mental disability, medical condition, family care status, or any other basis protected by law. We are an AA/Veterans/Disabled Employer. Cloudflare provides reasonable accommodations to qualified individuals with disabilities. Please tell us if you require a reasonable accommodation to apply for a job. Examples of reasonable accommodations include, but are not limited to, changing the application process, providing documents in an alternate format, using a sign language interpreter, or using specialized equipment. If you require a reasonable accommodation to apply for a job, please contact us via e-mail at [email protected] or via mail at 101 Townsend St. San Francisco, CA 94107.