Member of Technical Staff, AI Migrations

About Cockroach Labs

Cockroach Labs is disrupting the tech landscape by making it easier for companies to build and scale applications with CockroachDB. We're focused on tackling complex infrastructure challenges, particularly in database migrations, to create lasting impact for innovative companies worldwide. When our customers succeed, we all succeed.

The Role: Member of Technical Staff, AI Migrations

We are launching a dynamic engineering team dedicated to leveraging AI for one of the most complex challenges in infrastructure: database migrations. Migrations today are often slow, manual, and risky, especially with legacy stored procedures and deeply embedded business logic. Our mission is to radically simplify this journey by building intelligent tools that can translate, evaluate, and automate the most challenging aspects of moving data across systems.

As a founding member of this team, you will be instrumental in prototyping and launching cutting-edge systems:

• Build intelligent AI agents to modernize legacy SQL: Develop LLM-powered agents capable of analyzing and converting complex legacy SQL schemas and procedural logic into scalable, CockroachDB-native equivalents. This will unlock modernization at scale for enterprises with deeply entrenched database systems.
• Design an AI-powered migration strategist: Architect an LLM-driven engine that intelligently scans source schemas and real-world workload patterns to produce actionable, tailored migration plans. This system will offer dynamic guidance on what to migrate, how to do it, and what to watch out for, bringing clarity and confidence to a traditionally risky process.

This unique opportunity allows you to apply AI/ML to significant, real-world problems, operating with a startup mentality within a product-driven company. If you are passionate about building intelligent systems, thrive on solving meaningful problems, and want to move fast, own your work, and define a new frontier, we encourage you to apply.

Key Responsibilities

• Validate ideas through experimentation: Design and conduct focused experiments to explore how current AI tools can deliver real, incremental value in the migrations space.
• Test and iterate with AI approaches: Explore APIs like OpenAI and Anthropic, refine prompts, and tune context windows to optimize LLM performance on procedural translation and analysis tasks.
• Partner with domain experts: Collaborate closely with our migrations technical field community to deeply understand user pain points throughout the migration journey.
• Prototype fast, learn faster: Build proof-of-concept tools and agents from your findings, then utilize data and feedback to shape future development.
• Track progress and define success: Establish and monitor clear evaluation criteria, such as LLM accuracy or usability metrics, to guide the validation process.
• Build for scale: Transform promising experiments into scalable systems using Go, Python, and modern cloud infrastructure.
• Explore advanced patterns: Investigate sophisticated approaches like multi-step reasoning, agentic workflows, or integration with internal control planes (e.g., MCP).

Expectations for Your First Months

As an early team member, you will hands-on shape how AI is applied to database migrations. You will quickly transition from experimentation to implementation, collaborating with users and engineers to build impactful, usable tools.

• First Month: Get up to speed on the complexities of real-world database migrations, our current AI-native development approaches, and existing tool suites. You'll begin your initial experiments, identifying early signals for potential solutions.
• After 3 Months: You will have validated key assumptions regarding how AI can reduce migration friction and complexity. You'll be actively prototyping new tools and workflows, working closely with internal stakeholders, and contributing to the roadmap based on real results.

Qualifications

• Experimental mindset: Energized by ambiguous problems, rapid prototyping, and data-driven discovery.
• AI/ML technical foundation: Experience with LLMs, prompt engineering, and model evaluation from professional work, significant side projects, or deep technical exploration.
• Strong programming skills: Proficiency in Go, Python, or similar languages, with the ability to quickly learn new technologies and APIs.
• Greenfield experience: Background in building new products, prototypes, or research projects without predefined solution paths.
• Collaborative problem-solving: Experience working directly with internal stakeholders, gathering requirements, and iterating based on user feedback.
• Technical communication: Ability to clearly explain complex experimental results and technical concepts to diverse audiences.
• Experience level: Ideally 7+ years of software engineering experience, with hands-on work in AI/ML.

The Team

You will report to Adam Storm, a Fellow at Cockroach Labs, who brings over two decades of database industry experience and is focused on improving the customer migration experience to CockroachDB. Rima Deodhar, Senior Manager, Engineering, leads the CockroachDB Application and Developer Experience organization, which includes this team.

Work Environment

Cockroach Labs operates a hybrid work model. Roachers local to one of our offices attend on Mondays, Tuesdays, and Thursdays, working flexibly the rest of the week. We value in-person connection, creativity, and collaboration while embracing flexible work arrangements.

Benefits

Cockroach Labs offers a comprehensive Total Rewards package including stock options, medical, vision, and dental insurance, life and disability insurance, professional development funds, flexible paid time off, 11 paid holidays, 10 paid sick days, paid parental leave, a 401(k) plan, and mental wellbeing benefits.

Key skills/competency

• AI/ML
• LLMs
• Prompt Engineering
• Database Migrations
• SQL Modernization
• Python
• Go
• Cloud Infrastructure
• Experimentation
• Distributed Systems