About Crosby

Crosby is built on a simple conviction: a great legal system is the watermark of a great society — and the best legal work comes from combining human expertise with the right technology, not replacing one with the other.

Crosby is the first AI-native law firm, helping ambitious companies like Cursor, Ramp, and Cognition sign commercial contracts faster.

Legal work is both art and science, and we're mapping the frontier between the two — codifying what can be systematized, amplifying human judgment where it matters most. That's why the right way to bring AI into law isn't to sell software and walk away. It's to own the outcome together: higher-quality work, delivered faster. We build proprietary tools and human-in-the-loop workflows that change what's possible for corporate legal teams.

Crosby was founded by Ryan (Stanford Law, Cooley, startup GC) and John (Penn, first 15 engineers at Ramp). Help us transform one of society's most important industries.

About the role

As an AI Developer Experience Engineer at Crosby, you'll play a critical role in building the internal systems that enable our team to develop, evaluate, and ship AI features quickly and reliably. You’ll focus on improving the developer experience around LLMs, data, and experimentation — creating tools and infrastructure that accelerate iteration while maintaining quality.

You’ll partner closely with engineers, data scientists, and researchers to streamline workflows across prompting, evaluation, fine-tuning, and deployment. This role is for someone who is obsessed with leverage — building systems that make other engineers dramatically more productive.

What you'll do

Build AI developer tooling: Design and implement internal tools for prompt management, evaluation, experimentation, and model iteration.
Improve iteration speed: Create systems that enable rapid testing, debugging, and comparison of model outputs across different approaches.
Own evaluation infrastructure: Develop frameworks for benchmarking, regression testing, and monitoring AI system performance.
Streamline data workflows: Build pipelines and tooling to support data collection, labeling, and feedback loops for model improvement.
Support production systems: Partner with engineering teams to ensure AI features are reliable, observable, and easy to maintain in production.
Enable the team: Identify bottlenecks in the development process and build systems that increase developer velocity and confidence.

Who You Are

3+ years of software engineering experience, ideally working on developer tools, infrastructure, or platform teams
Strong proficiency in Python and 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 with the ability to design tools that scale across teams
Highly pragmatic with a focus on improving developer velocity and real-world outcomes
Strong communicator who can work closely with engineers, researchers, and product teams
Proactive, resourceful, and excited about building foundational systems in a fast-moving environment

Benefits & Perks

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

Equal Opportunity

Crosby is an equal opportunity employer. We do not discriminate based upon race, religion, color, national origin, sex (including pregnancy, childbirth, reproductive health decisions, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, genetic information, political views or activity, or other applicable legally protected characteristics.

Background checks for applicants will be administered in accordance with applicable law, and qualified applicants with arrest or conviction records will be considered for employment consistent with those laws, including the New York City Fair Chance Act.

Pursuant to New York Labor Law Section 194-b, the US Pay Range for this position is listed in the job post. Final compensation will be determined based on skills, experience, and qualifications.