Senior Machine Learning Engineer, Stripe Assistant

Who we are About Stripe

Stripe is a financial infrastructure platform for businesses. Millions of companies—from the world’s largest enterprises to the most ambitious startups—use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone’s reach while doing the most important work of your career.

The Stripe Assistant team is transforming how users interact with Stripe by building an intelligent and proactive assistant that not only answers users’ queries but efficiently resolves issues and provides valuable business insights. We leverage LLMs and agentic systems to elevate the user experience across Stripe—from the dashboard to support surfaces—and we enable other teams to build and integrate their AI agents on our platform.

We’re evolving from a helpful support tool to a trusted pilot that anticipates, optimizes, and executes on behalf of our users.

As a Staff Machine Learning Engineer on the Stripe Assistant team, you’ll own the end-to-end ML and agent architecture that makes Stripe Assistant safe, reliable, and deeply useful. You’ll set the strategy for how the Assistant executes high-trust actions, delivers accurate analytical answers across Stripe and the broader web, orchestrates capabilities across many tools and agents, and grounds responses in authoritative Stripe and user data—so users can resolve issues quickly and confidently.

You’ll drive conversation continuity and personalization across surfaces, evolve the Assistant into a proactive partner that anticipates user needs, and deepen its presence in the dashboard to streamline critical workflows. You’ll establish rigorous evaluation and SLOs and deliver step‑change improvements in quality, latency, cost, and availability—paving the way for configurable levels of autonomy and, ultimately, a dependable operating layer over a merchant’s Stripe account.

Our team operates fluidly and here are some problems you may tackle:

• Establish trustworthy, human-in-the-loop execution for high-trust “write” actions—prioritizing user control, transparency, accountability, and auditability so customers can delegate with confidence.
• Define and evolve the Assistant’s capability and governance model across hundreds of tools and agents, balancing power, permissions, and consistency at scale.
• Raise answer quality and usefulness by grounding in authoritative Stripe knowledge and live user data, building cross-surface memory and personalization, and making the Assistant proactive and present in the dashboard.
• Explore and apply optimal machine learning methods to improve Stripe Assistant’s overall performance, including but not limited to fine‑tuning LLMs with RLHF, synthetic data generation, optimizing RAG pipelines via domain‑specific embedding and retriever fine‑tuning, and automatic prompt tuning, etc.
• Make quality and reliability a product: set and meet SLOs, build rigorous evaluation and benchmarking loops, and drive sustained improvements in latency, cost, and availability.
• Lead as a tech lead: mentor and grow engineers, uphold high bars for code quality, security, observability, and operational rigor, and align cross‑functionally to ship safely and fast.

We’re looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirements, you are encouraged to apply. The preferred qualifications are a bonus, not a requirement.

• 8+ years in AI/ML and backend engineering (4+ years building and operating production ML systems) with technical leadership.
• Deep and up-to-date applied LLM experience: RAG/embeddings, tool use/function calling, agentic planning/orchestration, fine‑tuning, code generation, evaluations, etc.
• Proficient in Python (Ruby is a plus); strong distributed systems fundamentals.
• Experience working closely with product management, design, other engineers, and other cross‑functional partners.

• Experien…