Member of Technical Staff, AI Developer Experience

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