About Rippling
Rippling is the first way for businesses to manage all of their HR & IT—payroll, benefits, computers, apps, and more—in one unified workforce platform.
By connecting every business system to one source of truth for employee data, businesses can automate all of the manual work they normally need to do to make employee changes. Take onboarding, for example. With Rippling, you can just click a button and set up a new employees’ payroll, health insurance, work computer, and third-party apps—like Slack, Zoom, and Office 365—all within 90 seconds.
Based in San Francisco, CA, Rippling has raised $1.35B from the world's top investors—including Kleiner Perkins, Founders Fund, Sequoia, Bedrock, and Greenoaks—and was named one of America's best startup employers by Forbes (#12 out of 500)
We are building one of the most compliance-critical platforms in the company: the system responsible for filing payroll taxes for over
30,000 businesses and 1M+ employees across the United States
, growing 50% year-over-year.Tax filing is not just another product surface. It is a mission-critical platform where correctness, reliability, and automation directly impact financial liability, regulatory compliance, and customer trust. We are at an inflection point.As we scale rapidly, we are evolving from a functional tax filing system into a fully automated, reliable, and centralized compliance platform. We are hiring a
Staff Engineer
to own this transformation. This is a platform architecture and engineering leadership role — not a feature delivery position.
What You’ll Own
Platform Architecture
- Define the long-term technical architecture of the US Tax Filing platform
- Centralize tax calculation and filing logic into a deterministic, auditable core
- Establish strong domain boundaries across a hybrid monolith/microservice environment
- Drive architectural decisions that support scale, reliability, and compliance
Reliability & Automation
- Eliminate manual operational workflows through system design
- Architect idempotent, resilient filing pipelines
- Improve rejection handling and recovery flows with government agencies
- Build pre-submission validation and data quality enforcement layers
- Design systems that make year-end filing predictable and scalable
Explainability & Compliance Integrity
- Embed traceability and auditability into the core system
- Ensure we can clearly answer:
- Why was this tax calculated?
- Which rule version applied?
- What changed between filings?
- Improve reconciliation and reduce quarterly discrepancies
Engineering Culture & Quality
- Raise the bar on design rigor, reliability standards, and testing discipline
- Influence a team of 20 engineers, including 4 Staff Engineers
- Establish stronger observability, SLOs, and operational excellence practices
- Mentor senior engineers and shape technical strategy across teams
The Challenges
- 30,000+ customers and 1M+ employees — scaling at 50% YoY
- Highly complex federal, state, and local tax regulations
- Government e-file integrations with inconsistent APIs and legacy constraints
- Quarterly reconciliation edge cases
- Year-end filing at significant scale
- A system transitioning from partially distributed tax logic toward centralized domain ownership
- Eliminating manual interventions in a compliance-sensitive environment
This is a rare opportunity to architect and harden a system where zero-defect expectations meet high-scale distributed systems.
What We’re Looking For
- You are a systems thinker who thrives in high-stakes domains.
- You likely have:
- Experience owning architecture for large-scale distributed systems
- A track record of improving reliability and eliminating operational toil
- Strong domain modeling instincts
- Experience centralizing fragmented logic into coherent platforms
- Deep interest in determinism, correctness, and auditability
- The ability to influence across teams and elevate engineering culture
- Comfort operating in ambiguous, high-growth environments
- Experience in fintech, payroll, compliance systems, payments, or other correctness-critical domains is highly valued but not required.