Product Director

ABOUT DOTFILE Dotfile is building the AI-native Compliance Operating System for financial institutions. Our mission is to make compliance simple, safe and smart, helping financial institutions onboard customers, manage risk and operate globally. Compliance remains one of the most manual functions in financial services. While most institutions still rely on fragmented tools and human-driven workflows, we believe AI is enabling a fundamental shift toward autonomous compliance. Our ambition is to build Level 5 Compliance: software that can gather evidence, investigate complex situations, assess risk and execute defensible decisions under defined policies. Dotfile has grown into one of Europe’s fastest-growing compliance technology companies. Today, 100+ financial institutions across 15 countries rely on Dotfile for critical compliance operations, with a rapidly growing presence in the US. We recently raised our Series A from leading US and European investors and software operators. We’re now entering our next chapter: investing heavily in product and AI, expanding internationally, and building the team that can make Dotfile the global standard for compliance infrastructure. ROLE OVERVIEW 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 our customers to turn complex compliance problems into simple, powerful product experiences. You will own major areas of the product end-to-end: understanding the problem, designing the system, prototyping solutions, shipping with Engineering, and learning from how customers use them. This is a builder role. You will be expected to go deep into workflows, data models and technical constraints, work directly with engineers and designers, and prototype ideas yourself when that is the fastest way to move forward. You should care as much about how the underlying system works as you do about the user experience built on top of it. AI is at the core of Dotfile’s product. You will design systems where agents investigate, reason and act across complex compliance workflows, and use AI extensively in your own work to research, prototype and ship faster. You will lead a small Product team while remaining deeply involved in the work yourself. You will coach and develop the people on your team, raise the bar for product thinking and execution, and create the environment for them to do their best work. This is not a role where management means stepping away from the product. You will work directly with the CEO and CTO. KEY 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 yourself • 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 actually gets done, identify recurring problems and turn them into scalable product capabilities • Define clear measures of product success, use data and customer behavior to evaluate what we ship, and iterate quickly when something is not working • Continuously improve how we build product at Dotfile, using AI to accelerate research, analysis, prototyping, specification and execution ABOUT YOU • You have 6+ years of experience building software products, including significant ownership of complex B2B or infrastructure products • You have experience managing and developing product people, while remaining close to the product and comfortable owning problems directly yourself • You are deeply technical for a product leader. You are comfortable discussing APIs, data models, system architecture, integrations and technical trade-offs directly with engineers • You think in systems. You naturally look beyond individual features to understand the underlying primitives, abstractions and interactions that make a product scalable • You are extremely hands-on. You like getting into the details, exploring data, prototyping ideas and working directly with engineers and designers • AI is already deeply embedded in how you work. You use LLMs, coding tools and agents to research, analyze, prototype and build, and actively experiment with new capabilities as they emerge • You have strong product judgment and can turn ambiguous, complex problems into products that feel simple to users • You are comfortable building AI products where outputs are probabilistic and care deeply about evaluation, reliability, observability, human oversight and feedback loops • You thrive in a fast-moving environment with high standards and strong ownership, and know how to create that environment for the people you manage THE INTERVIEW PROCESS Round 1: First conversation to get to know you, understand what drives you, and explore why this role excites you. Round 2: Two-part discussion where you’ll walk us through your career journey and the choices that shaped it, followed by a values-based interview. Round 3: Deep dive into one of your key projects with someone from a different team, offering a fresh, cross-functional perspective on how you work. Round 4: Practical exercise, case study tailored to the role, giving you the opportunity to showcase your skills on a real-world challenge. Round 5: Final conversation with our founder.