Senior Machine Learning Engineer Applied AI Quality
Block, Inc. is a technology company building tools for economic empowerment, operating a portfolio of financial brands including Square, Cash App, Afterpay, TIDAL, Bitkey, and Proto. It serves sellers, consumers, artists, and bitcoin users through payments, banking, buy-now-pay-later, music streaming, and bitcoin self-custody and mining products.
About Block, Inc.
Block, Inc. builds technology aimed at increasing access to the global economy. Its brands each unlock different aspects of the economy: Square makes commerce and financial services accessible to sellers; Cash App is an easy way to spend, send, and store money; Afterpay (Clearpay in the UK) helps customers manage spending over time; TIDAL is a music platform empowering artists as entrepreneurs; Bitkey is a self-custody bitcoin wallet; and Proto builds open, accessible bitcoin mining hardware and services. Block has been a long-time advocate for bitcoin, integrating bitcoin buying/selling and Lightning Network payments into Cash App and Square, funding open-source bitcoin infrastructure through Spiral (including the Lightning Development Kit), and engaging in bitcoin policy advocacy through groups like COPA, the Digital Energy Council, the Crypto Council for Innovation, and the Texas Blockchain Council. The company also runs a significant open source program (contributing to projects like Goose, an on-machine AI developer agent, OkHttp, Retrofit, gRPC, Envoy, and MySQL) and an AI research effort, including co-founding the Agentic AI Foundation with Anthropic and OpenAI. Block serves individual consumers, small and medium-sized businesses/merchants, artists, and developers.
Skills
About the Role
You will lead the technical direction for AI-driven quality and evaluation systems. You will develop scalable systems using LLMs, agents, and behavioral signals to evaluate quality, detect regressions, and generate product insights. You will define evaluation and measurement approaches, translate organizational needs into technical roadmaps, influence engineering standards, lead cross-functional initiatives, and mentor engineers.
Requirements
- 5+ years of experience in software engineering, machine learning engineering, or applied AI.
- Experience designing and shipping large-scale AI and machine learning systems in production.
- Expertise with LLMs, agents, evaluation systems, retrieval architectures, and AI infrastructure.
- Ability to lead ambiguous, high-impact technical initiatives from concept through adoption across multiple teams.
- Experience defining technical strategy and influencing roadmaps.
- Communication and cross-functional leadership skills.
- Experience creating platforms, frameworks, and systems that enable other engineers and teams.
Responsibilities
- Lead the technical strategy and architecture for AI-driven quality and evaluation systems.
- Develop scalable systems that use LLMs, agents, and behavioral signals to evaluate quality, detect regressions, and generate product insights.
- Define long-term approaches for evaluation, measurement, and quality intelligence.
- Translate organizational needs into technical direction, roadmap priorities, and platform capabilities.
- Influence engineering standards and best practices for reliable, measurable, and trustworthy AI systems.
- Lead cross-functional initiatives spanning product, infrastructure, data, and applied AI.
- Mentor engineers through technical leadership, design reviews, and systems thinking.
- Identify opportunities for AI systems to improve product understanding, debugging, and behavior.
Benefits
- Remote work
- Medical insurance
- Flexible time off
- Retirement savings plans
- Family planning