Senior Staff Software Engineer - Monetization Platform

About Rippling

Rippling gives businesses one place to run HR, IT, and Finance. It brings together all of the workforce systems that are normally scattered across a company, like payroll, expenses, benefits, and computers. For the first time ever, you can manage and automate every part of the employee lifecycle in a single system.

Take onboarding, for example. With Rippling, you can hire a new employee anywhere in the world and set up their payroll, corporate card, computer, benefits, and even third-party apps like Slack and Microsoft 365, all within 90 seconds.

Based in San Francisco, CA,Rippling has raised $1.85B+ from the world’s top investors, including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, Bedrock, GIC, Elad Gil, and Goldman Sachs, and was named one of America's best startup employers by Forbes.

We prioritize candidate safety. Please be aware that all official communication will only be sent from @rippling.com addresses.

About Monetization Platform

The Monetization Platform team owns the systems behind how Rippling sells, contracts, bills, collects, and recognizes revenue across products and countries.

The team owns the platform behind the complete monetization lifecycle:

Quote → Contract → Entitlement → Subscription → Usage → Bill → Revenue

These systems support a $1B+ sales base, manage entitlements, metering, and usage-based billing rules, and enable localized billing as Rippling launches into new countries.

As Rippling continues to introduce new products, pricing models, packaging structures, and markets, the Monetization Platform provides the common infrastructure that allows teams to move quickly without rebuilding monetization logic each time.

Our vision is simple:

Let any team monetize any product, anywhere, without writing code.

This is a platform for engineers who enjoy solving foundational problems where correctness matters, abstractions need to last, and the impact extends far beyond a single product or team.

The opportunity

• Rippling's product portfolio is expanding rapidly across HR, IT, Finance, and new product categories.
• Every new product introduces monetization complexity: what a customer purchased, what they are entitled to use, how their subscription evolves, how usage should be measured, what they should be charged, how payments are collected, and how that activity is ultimately reflected in financial systems.
• We are hiring a Senior Staff Software Engineer to provide technical leadership for the next generation of Rippling's Monetization Platform.
• You will own broad, ambiguous, multi-team technical charters spanning contracts, entitlements, subscriptions, usage metering, billing, invoicing, payments, tax, compliance, and revenue workflows.
• You will work on systems where errors are expensive. Incorrect contract state, entitlement state, usage calculations, invoices, payments, taxes, or revenue records can directly affect customers, financial accuracy, and trust.
• This role combines:
• • Hands-on backend and platform engineering
  • Org-level architectural leadership
  • Technical leadership and mentorship
  • Cross-functional influence across Engineering, Product, Finance, Accounting, Revenue Operations, Payments, Security, and Data
• You will define architecture, make difficult technical tradeoffs, align teams around durable solutions, mentor technical leaders, and help build a platform that allows Rippling to monetize new products and markets faster and with greater confidence.
• This is not an architecture-only role. You will stay close to execution through design reviews, code reviews, debugging, prototyping, production investigations, and implementation-level technical decisions.

What you'll own

• Own major technical charters across CPQ, contracts, entitlements, subscriptions, usage metering, billing, invoicing, payments, tax, compliance, and revenue workflows.
• Define architecture for systems requiring strong guarantees around data integrity, auditability, reliability, recoverability, and clear ownership across service boundaries.
• Design durable platform abstractions that allow product teams to introduce new packaging, pricing, entitlement, metered billing, subscription, and contract models without building custom one-off solutions.
• Lead multi-team initiatives from problem definition and architecture through technical design, execution, migration, launch, and long-term operational ownership.
• Define clear service boundaries, APIs, data models, ownership models, and failure-handling strategies across interconnected monetization systems.
• Make high-quality technical tradeoffs across correctness, scalability, performance, cost, compliance, maintainability, and delivery speed.
• Stay hands-on through design reviews, code reviews, debugging, prototyping, production investigations, and implementation-level decisions.
• Partner closely with Product, Revenue Operations, Finance, Accounting, Payments, Platform, Security, Data, and product engineering teams.
• Identify systemic technical risks early and drive alignment on durable solutions, particularly where customer trust or financial accuracy is at stake.
• Establish engineering standards for critical monetization systems, including testing, observability, incident learning, migration safety, rollout mechanisms, and operational readiness.
• Mentor Staff, Senior, and mid-level engineers and help grow technical leadership across the organization.
• Raise the engineering bar through strong technical judgment, thoughtful design reviews, clear technical writing, and operational excellence.

What success looks like

• Platform leverage: Product teams can launch new products, pricing structures, packaging models, entitlement models, and usage-based offerings without rebuilding core monetization infrastructure.
• Correctness and trust: Critical contract, entitlement, subscription, billing, payment, tax, and revenue workflows maintain a high standard of data integrity, auditability, and reliability.
• Clear architectural boundaries: Monetization capabilities have well-defined ownership, APIs, data contracts, and service boundaries, reducing coupling and one-off implementations.
• Faster product and market expansion: New products and country launches can adopt common monetization capabilities rather than creating bespoke billing and entitlement systems.
• Operational excellence: Critical monetization systems have strong observability, safe migration patterns, effective incident learning, and clear operational ownership.
• Technical leadership: Engineers across teams look to you for architectural guidance, difficult technical decisions, and direction on complex cross-system problems.
• Stronger technical leaders: Staff, Senior, and mid-level engineers around you develop greater technical judgment, ownership, and ability to lead increasingly complex initiatives.

What we're looking for

• 15+ years of software engineering experience, preferably across backend engineering, platform engineering, infrastructure, distributed systems, product engineering, or systems engineering.
• Proven experience operating at Senior Staff, Principal Engineer, or equivalent Staff+ scope.
• Deep hands-on engineering foundation with strong coding, debugging, system design, and production ownership experience.
• Experience building and operating large-scale distributed systems with demanding reliability, observability, and data correctness requirements.
• Strong architecture depth across APIs, databases, data modeling, concurrency, event-driven systems, service boundaries, reliability, performance, failure modes, and long-term maintainability.
• Demonstrated ability to own ambiguous, cross-functional, multi-team technical initiatives from definition through production ownership.
• Strong technical judgment and the ability to make tradeoffs across product needs, business constraints, engineering quality, and long-term platform direction.
• Ability to influence senior engineers, product leaders, and cross-functional stakeholders without relying on formal authority.
• Strong mentorship record and a track record of raising the technical bar for engineers around you.
• Clear written and verbal communication, especially when explaining complex technical decisions to technical and non-technical audiences.
• Comfort operating in fast-paced, high-ambiguity environments.
• Deep backend programming experience in one or more languages. Python and Django experience is a strong plus.

Bonus points

• Experience building monetization, entitlement, metered or usage-based billing, subscription, pricing, payments, accounting, revenue, tax, or fintech systems.
• Experience building internal platforms used by multiple product engineering teams.
• Experience working in SaaS, enterprise software, HR technology, payroll, compliance, workflow-heavy domains, or high-growth product companies.
• Experience with MongoDB or similar NoSQL databases.
• Experience with reliability engineering, incident response, performance tuning, observability, and operational excellence.
• Experience with security, permissions, auditability, compliance, or enterprise-grade controls.
• A builder-leader mindset: someone who can define direction, align stakeholders, establish durable architecture, and remain close to execution.

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