Senior Director of Engineering, Cloudflare
Billing Platform
$273-341k
+ Equity. Salary is benchmarked based on US rates and may vary depending on the location
Web performance and security platform
Be an early applicant
Web performance and security platform
1001+ employees
Be an early applicant
$273-341k
+ Equity. Salary is benchmarked based on US rates and may vary depending on the location
1001+ employees
Company mission
To help build a better Internet that is bold and ambitious.
Role
Who you are
- 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
- 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
- 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
Desirable
- 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
What the job involves
- 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
- 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
- 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
Our take
Cloudflare is a multi-service global network that provides web security and infrastructure, DDoS mitigation services, and a content delivery network. Founded in 2009, Cloudflare has risen to become an industry giant, with over 25 million global internet properties on its network.
Cloudflare has been responsible for a number of admirable initiatives, offering free web protection to human rights groups, journalists, artists, and US election websites. This goes some way to counteracting the flak Cloudflare has received in some circles for the controversial groups and users who use its services. This chequered history, however, has not affected its over 80% market share in the content delivery network field.
This is perhaps in part because it has proven sharp at staying abreast of the rapidly morphing tech and digital space and customer demands. For example, Cloudflare is shifting to 100% renewable energy usage to create a zero-emissions internet, and in 2020 released a feature that would help users navigate data privacy regulations by selecting where their data is stored.
And impressive third-quarter 2025 results show strong momentum, with revenue rising to $562 million from $430 million a year earlier. The company also raised its full-year guidance, underscoring confidence in continued growth. As demand for secure, cloud-based infrastructure keeps growing, Cloudflare's expanding platform and improving efficiency leave it well positioned to capture further gains in a rapidly growing market.
Steph
Company Specialist at Welcome to the Jungle
Insights
16% employee growth in 12 months
Company
Company benefits
- Competitive pay: We offer a competitive total rewards package, where every employee is an owner of our stock.
- Take-what-you-need vacation: We encourage employees to find a comfortable work-life balance by taking as many days off as they need while still being able to perform their jobs satisfactorily. (We really mean it!)
- Paid maternity & paternity leave: Our global parental leave policy allows up to sixteen paid weeks of bonding leave time for all qualifying new parents.
- Employee benefits: We offer a comprehensive benefits package including healthcare, life insurance, short- and long-term disability, pension plans in accordance with the market practice in our locations.
- Commuter program: We are flexible about where we work and value connecting at the office. Our commuter benefits program is in place to support team members' commute to work via public transportation without the extra cost burden.
- Wellbeing: Global offerings that provide mental health, childcare and family forming support to our employees across our offices.
Company HQ
China Basin, San Francisco, CA
Leadership
Lee Holloway
(Co-Founder & Lead Engineer)Lee began their career as an Engineer at Homewarehouse for a year before working at Unspam Technologies for 4 years. They co-created Project Honey Pot in 2004 and Cloudflare in March 2009, serving as Lead Engineer of both to present.
Michelle Zatlyn
(Co-Founder, President & Co-Chair)Having worked for Investor Economics and I Love Rewards for a combined 4 years, Michelle worked at Toshiba for 3 years as a Product Manager. She then co-founded Cloudflare in 2009 as COO, and has served as President since 2020. She is also a Board Member at Atlassian.
Matthew Prince
(Co-Founder & CEO)Matthew studied for an MBA at Harvard Business School before co-founding Unspam Technologies in December 2001, and Cloudflare in 2009, where he has served as CEO ever since.
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