Staff Machine Learning Engineer - AI Cloud

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 $1.4B+ from the world’s top investors—including Kleiner Perkins, Founders Fund, Sequoia, Greenoaks, and Bedrock—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 The Role At Rippling, we are not just building AI features, we are building an autonomous operating system for work. We are investing heavily in the next generation of enterprise AI: intelligent background automation, systems that monitor and improve themselves, and a custom intelligence layer built on Rippling’s unique data and workflows.

The opportunity is to push the boundaries of what machine learning can do in the enterprise through purpose-built ML systems that learn from Rippling’s proprietary data graph to deliver compounding intelligence across every product surface.

You will be joining the team that recently launched Rippling AI, the fastest-growing product in Rippling’s history. The models and ML systems you build will be the intelligence powering every AI surface at Rippling.

As a Staff Machine Learning Engineer, you will own the end-to-end ML lifecycle: problem formulation, data strategy, model development, evaluation, and production deployment. You will lead technical direction for ML initiatives across the AI org and drive the science that makes Rippling’s agents reliable, accurate, and continuously improving. This is a deeply hands-on role.

What You Will Do

• Own the end-to-end machine learning lifecycle for high-impact AI initiatives
• Design and implement novel ML architectures (fine-tuned LLMs, RAG, reward models, multi-agent orchestration) tailored to Rippling’s enterprise domain
• Build robust evaluation and experimentation infrastructure: offline benchmarks, A/B testing, and continuous monitoring of model quality Develop training pipelines and data flywheels that leverage Rippling’s structured data graph
• Lead research-to-production efforts: identify where frontier techniques (RLHF, distillation, structured decoding, tool-use training) unlock step-function improvements
• Design self-improving systems: feedback loops, active learning, and automated retraining pipelines
• Partner closely with Product and Platform teams
• Mentor engineers across the org on ML best practices
• Track the frontier of ML research and translate breakthroughs into production systems

What You Will Need

• 8+ years of software engineering experience with 5+ years focused on ML, shipping ML systems to production at scale
• Deep expertise in modern ML: LLMs, transformer architectures, fine-tuning, RLHF, RAG
• Strong fundamentals in classical ML and statistics
• Hands-on proficiency with ML frameworks (PyTorch, JAX) and production ML infrastructure
• Experience building evaluation systems for generative AI
• Proven ability to lead complex, cross-functional technical initiatives
• Strong product instincts
• Clear, precise communication to diverse audiences
• Comfort with ambiguity and high velocity
• Publications in top ML venues (NeurIPS, ICML, ACL, EMNLP) are a plus
• Experience with enterprise data or knowledge graphs is a plus

Additional Information Rippling is an equal opportunity employer. We are committed to building a diverse and inclusive workforce and do not discriminate based on race, religion, color, national origin, ancestry, physical disability, mental disability, medical condition, genetic information, marital status, sex, gender, gender identity, gender expression, age, sexual orientation, veteran or military status, or any other legally protected characteristics, Rippling is committed to providing reasonable accommodations for candidates with disabilities who need assistance during the hiring process. To request a reasonable acc…