Head of Design / Principle Designer

About BoostDraftBoostDraft is reinventing legal drafting with a local Microsoft Word add-in that automates tedious formatting and elevates lawyers’ day-to-day work. Founded by MIT and Stanford alumni, we’ve grown to 10,000+ paying users and earned adoption at 17 of Japan’s top 20 law firms—mostly through word-of-mouth, profitability, and without external funding until January, 2025. Company Slides: Why you should join BoostDraft You can enjoy the whole process of product market fit, and scale the business A lot of opportunities to learn from the founders / management, including leveraging our Japan experience and product development International environment with significant challenges to be met every day Lots of opportunities to interact with industry leaders who are focused on delivering products that offer exceptional user experiences You will use the latest technologies and will be encouraged to bring your flair to the role What’s your challenges Drive user insight through rapid exploration Own and lead our user research practice, with a strong bias toward early, prototype-driven user testing. Default to using AI-assisted prototyping to quickly explore ideas, validate assumptions, and surface risks before engineering investment. Turn ambiguous feedback and fragmented requests into clear hypotheses, prototypes, and learnings that guide product direction. Set the bar for product design Define and evolve our design philosophy and principles, including how we balance speed vs. polish and AI-enabled workflows vs. traditional processes. Ensure design decisions are grounded in evidence from real users, not opinions or hierarchy. Make design a force multiplier Build, scale, and maintain a design system that encodes user insight and enables teams to move fast with confidence. Champion modern tools and workflows—especially AI—that reduce cycle time from idea → prototype → user feedback → decision. Lead and grow the design team Lead and coach a team of product designers to