# Principal Engineer, AI Systems

**Company:** [Square](https://hotfix.jobs/companies/square)
**Location:** Remote
**Role:** ML Engineering
**Salary:** $319k – $479k/yr
**Experience:** 15+ years
**Skills:** Python, LLMs, Prompt Engineering, RAG, Fine-Tuning, RLHF, Agent Orchestration, Multi-Agent Systems, Model Optimization, Production Ai Systems
**Posted:** 2026-06-10

> Principal-level IC building and scaling production autonomous agents and agentic workflows across Block's ecosystem using frontier LLMs. Requires 15+ years experience shipping AI systems from zero to production scale.

## Job Description

## Responsibilities
- Ship, architect, build, and own end-to-end delivery of autonomous agents and agentic workflows that deliver real business value for Block, ensuring reliability, safety, and performance at scale
- Design agent orchestration systems including planning, tool use, memory, evaluation, and multi-agent coordination at production scale
- Integrate and optimize frontier LLMs into agent architectures, making decisions on model selection, fine-tuning, prompt engineering, and context retrieval strategies
- Drive deeper model optimization work (fine-tuning, distillation, RLHF) where it unlocks agent capability or efficiency
- Lead detailed technical planning by breaking down ambitious objectives into concrete, sequenced tasks with clear ownership and execution paths
- Provide technical mentorship and guidance to engineers across experience levels, elevating team capabilities through code review, pairing, and knowledge sharing
- Partner closely with technical and non-technical stakeholders to translate business objectives into agent-powered product experiences
- Keep Block at the frontier by continuously evaluating emerging AI capabilities and making pragmatic tradeoffs across model performance, latency, cost, and user experience
- Foster a culture of technical excellence, high-quality delivery, rapid experimentation, and learning within your team and beyond

## Requirements
- 15+ years of experience in software engineering or machine learning, with recent professional experience building autonomous agents or agentic workflows in production
- Deep experience building autonomous agents or agentic workflows in production environments—not just prototypes or demos
- Fluency in the core primitives of agentic systems: context management, planning, tool use, memory, evaluation, and multi-step reasoning
- Experience bringing frontier LLM capabilities into production products, with hands-on experience in prompt engineering, retrieval-augmented generation, and model optimization
- A track record of taking AI-powered products from zero to scale in fast-paced, product-driven environments, with the judgment that comes from operating in production
- Strong software engineering fundamentals with the ability to write production-quality code and make sound architectural decisions
- Experience providing technical leadership within teams—you've shaped technical direction, driven execution, and elevated others
- Product-minded engineering approach—you think in terms of user outcomes, not just model metrics
- Excellent collaboration and communication skills, with ability to build alignment across engineering, product, and design
- Comfort navigating extreme ambiguity in a domain that's evolving weekly
- Alignment with Block's mission of economic empowerment and using technology to create access and opportunity

## Nice-to-Haves
- Experience at leading AI organizations with a track record of translating research into production agent systems
- Background building or scaling agentic products at startups (including early-stage or pivoting companies)
- Experience with model fine-tuning, distillation, or RLHF to improve agent performance
- Familiarity with agent evaluation, safety, and alignment challenges in production contexts

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