Naboo - Head of Engineering

Are you ready to join Connecticut Innovation’s vibrant community of innovators? Connecticut Innovations (“CI”) is Connecticut’s strategic venture capital arm, and we are passionate about serving our portfolio of 220+ companies across various industries, with strengths in life sciences, technology, and climate tech.

Come join Naboo | Enterprise Context Layer for AI Agents & Developers!

This role partners with the Founders to provide architectural clarity, hands-on technical leadership, and strong engineering execution. As Naboo scales, the Head of R&D scope is expected to evolve toward broader organizational leadership and execution.

About Naboo

At Naboo.ai, we harness the power of artificial intelligence to transform data into actionable insights. Our cutting-edge platform integrates advanced analytics and machine learning, enabling businesses to streamline operations, enhance customer experiences, and drive innovation.

We provide an AI context layer that feeds engineering and agent workflows with precise, intent-aware data from code, logs, tickets, and documentation. Unlike generic retrieval stacks, Naboo maps software context, so AI agents and copilots can execute actions reliably instead of guessing. Our user-friendly tools empower teams to make informed decisions faster, adapt to market changes, and unlock new growth opportunities.

Join us on our mission to make intelligent decision-making accessible for everyone. Naboo | Enterprise Context Layer for AI Agents & Developers

Head of Engineering/R&D | Position Overview

Head of R&D will be responsible for defining and executing Naboo’s overall technology strategy, ensuring the platform’s architecture, AI capabilities, and engineering execution support the company’s product vision and long-term scalability. This role combines deep technical leadership with hands-on engagement in a highly differentiated, early-stage enterprise AI company.

This role is situated in an early-stage, high-growth environment. Success requires comfort operating with ambiguity, evolving requirements, and limited formal process, while maintaining strong technical judgment, ownership, and execution discipline.

Job Duties and Responsibilities

In addition to the responsibilities below, success will be measured in tangible delivery within the first year of several self-service use cases that create a repeatable adoption motion

• Own Naboo’s end-to-end technology strategy, architecture, and engineering execution.
• Partner closely with the Founders to translate Naboo’s core technical differentiation into a robust, scalable enterprise platform.
• Provide hands-on technical leadership across AI/ML, data platforms, and system architecture, particularly in the company’s early stages.
• Lead and mentor the engineering and applied AI teams, setting high standards for design, code quality, reliability, and security.
• Guide architectural decisions around data infrastructure, model integration, evaluation frameworks, and production AI systems.
• Balance rapid experimentation with enterprise-grade robustness, scalability, and compliance.
• Collaborate with Founders and Product to support customer engagements, technical due diligence, and partner relationships.
• Establish engineering processes, metrics, and hiring standards appropriate to Naboo’s stage of growth.

Skills You Must Have

• 12+ years of experience in software engineering and technology leadership, including senior technical roles in comparable AI-driven technology ecosystems.
• Deep expertise in AI/ML systems, data platforms, or applied intelligence, with experience bringing complex AI capabilities into production.
• Proven ability to design and scale complex, distributed systems in enterprise environments.
• Prior experience in early-stage or high-growth companies, with demonstrated comfort building from first principles.
• Strong communication skills and ability to engage credibly with technical and non-technical stakeholders, including customers and investors.
• Experience in adjacent domains such as data infrastructure, analytics platforms, or enterprise AI software may be considered equivalent to direct domain experience.

Naboo is proud to be an equal opportunity workplace. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Naboo is committed to working with and providing reasonable accommodation to applicants with physical and mental disabilities