Product Director

Dotfile is building the AI-native Compliance Operating System for financial institutions. We are looking for a highly technical, hands-on Product Director to help define and build the next generation of Dotfile. You will work at the intersection of Product, Engineering, Design and customers to turn complex compliance problems into simple, powerful product experiences, lead a small Product team while remaining deeply involved in the work, and work directly with the CEO and CTO.

Responsibilities

Own major product areas end-to-end, from understanding the problem and defining the underlying system to shipping, adoption and iteration; Lead and develop a small Product team, setting a high bar for product thinking, execution and ownership while remaining deeply hands-on; Turn complex compliance workflows into simple, programmable product experiences that can scale across customers, use cases and jurisdictions; Work closely with Engineering and Design on product architecture, data models, workflows and technical trade-offs; Design how AI agents interact with data, users and other systems to investigate cases, make recommendations and increasingly automate compliance work; Prototype ideas quickly using AI and modern development tools to explore interactions, validate concepts and communicate what should be built; Spend significant time with customers and internal teams to understand how compliance gets done and turn recurring problems into scalable product capabilities; Define clear measures of product success, use data and customer behavior to evaluate what ships, and iterate quickly; Continuously improve how product is built at Dotfile, using AI to accelerate research, analysis, prototyping, specification and execution

Requirements

6+ years of experience building software products, including significant ownership of complex B2B or infrastructure products; Experience managing and developing product people while remaining close to the product; Deeply technical for a product leader, comfortable discussing APIs, data models, system architecture, integrations and technical trade-offs with engineers; Thinks in systems and looks beyond individual features to underlying primitives, abstractions and interactions; Extremely hands-on, comfortable exploring data, prototyping and working directly with engineers and designers; Uses LLMs, coding tools and agents to research, analyze, prototype and build; Strong product judgment and ability to turn ambiguous, complex problems into simple products; Comfortable building AI products with probabilistic outputs, with care for evaluation, reliability, observability, human oversight and feedback loops; Thrives in a fast-moving environment with high standards and strong ownership