Founding Head of Engineering - Python, LLM, AI

We are the #1 AI lawyer for small to midsize businesses. We combine AI, our own law firm, and an expert feedback loop to deliver fast, compliant, high-quality legal work at a fraction of the cost and turnaround time of traditional firms. We grew revenue 1,500% last year.

What you will be doing:

-Take ownership of the vision and development of agentic AI.

-This is a technical leadership and hands-on role for someone who has already built agentic AI systems and has improved them while in production.

-You will own architecture and delivery, and set the engineering standard for how this work gets done.

-You will work directly with lawyers to translate legal workflows into reliable AI systems.

-You will also serve as a team lead and play a critical role in hiring, managing and scaling the AI engineering team.

-Architect expert feedback loop, agents and knowledge base

-Develop an agent architecture with a knowledge base which can be used to dynamically insert expert feedback based on user context.

-Determine the process to convert feedback from our legal team's daily operations into knowledge base updates which can rapidly improve agent performance.

-Build evaluation infrastructure - including LLM-as-a-judge evals, feedback capture and regression testing.

-Establish best practices for versioning, testing, deployment, and observability.

-Build features to gather user context while minimizing user effort (e.g., using web search and integrations like email, google drive) and using long-term and short-term memory to improve performance.

-Build tools to facilitate lawyer input into knowledge base updates, evals and other inputs to the agentic system that improve quality of results over time.

-Monitor production systems, flag and resolve bugs

-Stay on the frontier of both AI and legal AI

What you need:

-10+ years of software engineering experience (3+ yrs in Python)

-5+ years tech lead experience: you've owned architecture decisions, led development, handled deployment and monitoring

-Hired and managed software engineers

-1+ year building agentic systems in production, particularly

-Built systems with reasoning about goals, planning, tool calls and subagents

-Built context management and memory for agentic systems

-Built LLM-as-a-judge or similar evaluation frameworks

-Built expert-in-the-loop systems where domain experts continuously improve accuracy

-Experience working in an AI-native development manner using tools such as Claude Code, Cursor, Codex, or similar

-Worked in startup environment with high ambiguity, urgency, and ownership

-Experience with frontend or workflow UI development sufficient to collaborate effectively across the product stack

Benefits

-Competitive salary and meaningful founding engineer level equity

-Unlimited PTO

-High impact work: Build the AI at the center of the largest and fastest growing legal AI product

-Fully covered health, dental, and vision.