Director of AI

We are seeking a Director of AI to own the AI technology strategy, architecture, and execution for a small, highly technical startup building a B2B legal SaaS platform where AI is the core product capability. This role reports directly to the CTO and is a hands‑on leadership position for someone who wants to build, ship, and scale applied AI in a company where the work is central to product success.

This is not a pure management role. Initially, roughly 75% of the role will be hands‑on technical work and 25% will be team leadership and management . You will be expected to make key technical decisions yourself, build critical systems, and help recruit and lead a small team of senior generative AI engineers.

• Own the company’s AI/ML technology and feature direction across the product
• Define and execute the technical AI roadmap, balancing near‑term product delivery with longer‑term platform investment, technical debt reduction, and strategic innovation
• Deliver technical, product, and operational outcomes tightly aligned with company goals and overall business success
• Hire, mentor, and manage a small team of senior generative AI engineers (Expected team size: 2–5)
• Partner closely with Product Management and Project Management to balance new feature delivery against execution of the technical roadmap
• Lead architecture and implementation for core AI systems including:
  • LLM‑based workflows
  • RAG systems
  • AI agents
  • Evaluation and testing systems
  • Observability and performance monitoring
  • Model selection and routing
  • Data ingestion and retrieval systems
• Own major parts of the company’s data ingestion pipeline into platform storage and analytics systems, including ETL‑related design and execution where it supports AI product capabilities
• Work across graph databases, traditional databases, retrieval systems, and analytics infrastructure to support product quality and scale
• Own the AI vendor and external service provider budget, with responsibility for evaluating cost, performance, and strategic fit
• Evaluate proprietary and open‑source model options, and select the right models for the right tasks
• Build infrastructure to host LLMs in the company’s new data center environment using company‑provided hardware
• Establish strong experimentation and measurement practices for AI features, including A/B testing, offline evaluations, and production‑informed assessment loops
• Serve as an internal evangelist for effective use of AI agents inside the engineering organization, especially for coding workflows
• Maintain and continuously improve a practical set of coding agents and AI‑assisted engineering practices that help the team produce better software

Why this role matters

AI is not an add‑on for this company. It is the product. The person in this role will shape the technical direction of the business, build the systems that determine product quality and differentiation, and help define how a modern AI‑first legal SaaS company operates.

Requirements

• 15+ years of experience in software engineering, machine learning, AI, or closely related technical fields
• Proven track record building and shipping production AI/ML systems
• Strong hands‑on depth with modern AI systems, especially in areas such as:
  • LLMs
  • generative AI applications
  • RAG
  • agents
  • model evaluation
  • observability
  • data pipelines / ETL
  • vector, graph, and relational data systems
• Experience selecting, integrating, and operating external AI vendors and services with cost accountability
• Experience evaluating and deploying open‑source models in production or near‑production environments
• Strong system design judgment and the ability to move fluidly between architecture, implementation, and operational execution
• Comfort operating in an early‑stage, pre‑revenue startup where speed, ownership, and technical judgment matter
• Ability to lead senior engineers while remaining deeply involved in design and execution