Billing Platform Engineering Executive

CloudFlare; Canada; Hybrid; CAD 388,000 - 527,000; Full time

Job summary

Cloudflare is seeking a Senior Director of Engineering for the Billing Platform to steer the multi-year strategy and architecture of usage-based billing, invoicing, payments, and tax within a hybrid work model. You will lead a large, distributed team of engineering managers and product engineers, aligning Product, Finance, and Revenue Ops to deliver durable, scalable systems.

The role emphasizes leadership of managers, strong engineering judgment, and collaboration with executive stakeholders to

Qualifications

• 15+ years of software engineering experience, including 7+ years leading engineering teams and 3+ years directly.

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.

Skills

Software engineering

Leadership

Manager of managers

Job description

Cloudflare is seeking a Senior Director of Engineering for the Billing Platform to steer the multi-year strategy and architecture of usage-based billing, invoicing, payments, and tax within a hybrid work model. You will lead a large, distributed team of engineering managers and product engineers, aligning Product, Finance, and Revenue Ops to deliver durable, scalable systems.

The role emphasizes leadership of managers, strong engineering judgment, and collaboration with executive stakeholders to