Director of Engineering, Core AI Experience

Retool•San Francisco, CA

About The Position

Retool is seeking a Director of Engineering to lead its Core AI Experience: product experiences that help people turn business problems into working software with AI. The role will shape how users move from an idea to an app or agent connected to real data, and how they test, refine, and confidently put what they build into use. The Director will lead work to make AI-assisted software creation quick for initial versions while remaining intuitive, reliable, and useful as customer requirements become more complex. The experience should help users understand and guide what AI builds and move fluidly between AI generation and direct editing. At the intersection of product engineering, developer experience, and applied AI, this role partners closely with Product and Design to define the core experience, make technical investments that improve quality and speed, and build teams that learn quickly from customers. The position calls for strong product judgment, technical depth, and the ability to turn an ambitious direction into focused execution.

Requirements

Experience leading multiple product engineering teams, with a track record of developing managers and senior engineers.
Strong product instincts and experience partnering deeply with Product and Design to deliver intuitive, technically complex software.
Technical depth in interactive applications, developer tools, or similarly complex products where frontend experience and underlying systems are closely connected.
Experience shipping AI-powered products and understanding the challenges of model variability, latency, evaluation, and user trust.
Judgment to distinguish where experimentation will help a team learn and where a more durable technical investment is needed.
Track record of turning ambiguous opportunities into clear priorities and helping teams make progress as requirements evolve.
Strong communication and organizational leadership, including creating alignment, surfacing risks early, and making decisions understandable.
A practical, involved leadership style, with the ability to move between organizational strategy, technical reviews, and detailed product discussions as needed.

Nice To Haves

Experience with AI-assisted software creation, developer workflows, or enterprise software.

Responsibilities

Own engineering strategy and execution for Retool’s Core AI Experience, connecting the long-term product vision to clear priorities and measurable customer outcomes.
Partner with Product and Design to shape how users build, edit, debug, and iterate on software with AI, from their first interaction through ongoing use.
Collaborate with go-to-market teams on product launches, positioning, and sales strategy.
Lead and develop engineering managers and senior technical leaders, building clear ownership and strong collaboration across teams.
Set a high bar for product quality, including the reliability, responsiveness, and usability of AI interactions.
Guide architectural decisions across the user experience, application state, AI orchestration, and connections to the broader Retool platform.
Build effective ways to evaluate AI behavior, combining customer feedback, product data, and systematic evaluations to determine whether changes improve the experience.
Help teams balance rapid experimentation with the engineering foundations needed to support increasingly complex customer use cases.
Work with platform and infrastructure partners to ensure the core experience meets enterprise requirements for data access, permissions, and governance.
Stay close to customers and the work, helping teams resolve ambiguity, make tradeoffs, and ship.