Category-defining tech. Career-defining work.

Lots of tech companies disrupt. But, many fail when they try to scale. We're different. CockroachDB makes it easier for companies to build and scale apps. This is how and why we're helping some of the most innovative companies on the planet. We tackle problems head-on and focus on solutions that create lasting impact.

Because when our customers win, we all win.

The Role

We’re launching a fast-moving engineering team focused on applying AI to one of the most complex and underserved challenges in infrastructure: database migrations.

Migrations today are slow, manual, and risky—especially when they involve legacy stored procedures and deeply embedded business logic. Our goal is to radically simplify this journey by building intelligent tools that can translate, evaluate, and automate the hardest parts of moving data across systems.

As a founding member, you’ll help prototype and launch cutting-edge systems such as:

• Build intelligent AI agents to modernize legacy SQL: Develop agents powered by LLMs that can analyze and convert complex legacy SQL schemas and procedural logic into scalable, CockroachDB-native equivalents—unlocking 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 go beyond static analysis, offering smart, dynamic guidance for what to migrate, how to do it, and what to watch out for—bringing clarity and confidence to a traditionally risky process.

This is a unique opportunity to apply AI/ML to deep, real-world problems and to operate like a startup within a product-driven company. If you’re passionate about building intelligent systems that solve meaningful problems—and want to move fast, own your work, and help define a new frontier—we’d love to hear from you.

You Will

• Validate ideas through experimentation: Design and run focused experiments to explore how today’s AI tools can help us 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 how LLMs perform on procedural translation and analysis tasks.
• Partner with domain experts: Collaborate closely with our migrations technical field community to deeply understand the pain points users face throughout the migration journey.
• Prototype fast, learn faster: Build proof-of-concept tools and agents from your findings, then use data and feedback to shape what comes next.
• Track progress and define success: Establish and monitor clear evaluation criteria (like LLM accuracy or usability metrics) to guide the validation process.
• Build for scale: When experiments show promise, turn them into scalable systems using Go, Python, and modern cloud infrastructure.
• Explore advanced patterns: When the time is right, dive into more sophisticated approaches like multi-step reasoning, agentic workflows, or integrating with our internal control planes (e.g., MCP).

The Expectations

As an early team member, you’ll be hands-on shaping how we apply AI to one of the most challenging areas in data infrastructure: database migrations. You'll move quickly from experimentation to implementation, working closely with users and engineers to build real, usable tools that make a difference.

In the first month, you’ll be up to speed on the complexity of real-world database migrations, the current AI-native development approaches we use, and the suite of tools already in place. You'll begin running your first experiments, identifying early signals for what might work.

After 3 months, you'll have validated key assumptions around how AI can reduce migration friction and complexity. You'll be actively prototyping new tools and workflows, working closely with internal stakeholders, and helping define the roadmap based on real results.

You Have

• Experimental mindset: You're energized by ambiguous problems, rapid prototyping, and discovering solutions through data-driven experimentation
• AI/ML technical foundation: Experience with LLMs, prompt engineering, and model evaluation through 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 building new products, prototypes, or research projects where the solution path wasn't predefined
• Collaborative problem-solving: Experience working directly with internal stakeholders, gathering requirements, and iterating based on user feedback
• Technical communication: Ability to 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

Rima Deodhar - Senior Manager, Engineering

Rima joined Cockroach Labs in 2021 and leads the CockroachDB Application and Developer Experience organization, which includes the Disaster Recovery, CDC, and Migrations teams. She brings over a decade of experience in large-scale, distributed systems. Outside of work, Rima enjoys reading, cooking, and traveling with her family.

Isaac Wong - EVP of R&D

Isaac is responsible for the health of the engineering organization at Cockroach Labs. He partners closely with teams to ensure we have a balanced culture that promotes quality and innovation in pursuit of our goals. Before joining Cockroach Labs Isaac was in life sciences for 16 years with Medidata Solutions where he had a front row seat on the exciting ride from a 30 person startup to more than 2000 people worldwide. But the lure of distributed, resilient, and consistent SQL databases, along with the amazing technology and culture at Cockroach Labs proved too much. When not working he likes to draw, play the piano, and search NYC for cannolis with his wife and kids.

Cockroach Labs is proud to be an Equal Opportunity Employer building a diverse and inclusive workforce. If you need additional accommodations to feel comfortable during your interview process, please email us at [email protected].

Cockroach Labs has a hybrid work model, with Roachers that are local to one of our offices coming in on Mondays, Tuesdays, and Thursdays and working flexibly the rest of the week. While we’ve learned valuable lessons working remotely, nothing can replace the connection, creativity, and fun that occurs when Roachers get together and we are committed to fostering a workplace that encourages collaboration and allows us all to do our best work.

Benefits

• Stock Options
• Medical Insurance
• Vision Insurance
• Dental Insurance
• Life and Disability Insurance
• Professional Development Funds
• Flexible Time Off
• Paid Holidays
• Paid Sick Days
• Paid Parental Leave
• Retirement Benefits
• Mental Wellbeing Benefits
• And more!