Senior Director of Engineering, Billing Platform

Cloudflare•San Francisco, CA

8d•Hybrid

About The Position

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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.

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
Short and Long Term Disability Insurance
Life & Accident Insurance
401(k) Retirement Savings Plan
Employee Stock Participation Plan
Flexible paid time off covering vacation and sick leave
Leave programs, including parental, pregnancy health, medical, and bereavement leave