Member of Technical Staff, AI Developer Experience

The role

You will build internal systems to enable the team to develop, evaluate, and ship AI features. You will focus on improving the developer experience around LLMs, data, and experimentation.

What you will do

• Design and implement internal tools for prompt management, evaluation, experimentation, and model iteration.
• Create systems that enable rapid testing, debugging, and comparison of model outputs.
• Develop frameworks for benchmarking, regression testing, and monitoring AI system performance.
• Build pipelines and tooling to support data collection, labeling, and feedback loops.
• Partner with engineering teams to ensure AI features are reliable, observable, and easy to maintain.
• Identify bottlenecks in the development process and build systems that increase developer velocity.

Required qualifications

• 3+ years of software engineering experience
• Strong proficiency in Python
• Experience building backend systems and internal tooling
• Hands-on experience working with LLMs, APIs (e.g., OpenAI, Anthropic), and modern AI workflows
• Experience building systems for experimentation, evaluation, or data pipelines
• Strong systems thinking
• Strong communicator

Nice to have

• ideally working on developer tools, infrastructure, or platform teams

Benefits

• Unlimited PTO
• Lunch & dinner in the office every day
• Medical insurance (multiple plan options through Anthem & Cigna)
• HSA or FSA, depending on your plan choice
• Dental insurance
• Vision insurance
• One Medical membership
• 401(k) match
• In-office desk setup stipend

Before you apply

• Background checks for applicants will be administered in accordance with applicable law

About the company

Crosby is an AI-native law firm that builds proprietary tools and human-in-the-loop workflows. It was founded by Ryan and John.