Head of Design / Principal Designer

About BoostDraft BoostDraft 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. 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 adopt prototype-first, research-led workflows. Set expectations that learning happens through making, testing, and iterating—not long handoffs or static specs. Stay hands-on when needed: prototyping, testing flows with users, and unblocking high-impact work. Partner deeply across the company Work shoulder-to-shoulder with Product and Engineering to ensure learning velocity drives roadmap and prioritization. Help the organization build shared understanding of users through prototypes, narratives, and clear synthesis—not just documents.com/boostdraft ---------- Ensuring a Fair and Secure Recruitment Process: In recent years, there has been a growing number of applications submitted with fake or AI-generated profiles, including fabricated work history or impersonated identities. At BoostDraft, we are committed to providing a fair and secure hiring process for all candidates and have implemented the following measures: During online interviews, the use of both camera and microphone is mandatory . If we detect suspicious behavior, we may ask you to disable video filters or perform a simple on-screen action . If you are unable or unwilling to comply, the interview may be terminated on the spot . By applying for a position or participating in an interview, you are deemed to have agreed to these measures and to cooperate if such requests are reasonably made. These measures are applied equally to all candidates to ensure a trustworthy and fair hiring environment. We appreciate your understanding and cooperation. If you have any concerns or questions regarding these measures, please feel free to contact our recruiting team. Requirements Fluency in qualitative user research , especially concept testing, usability testing, and workflow validation Strong experience leading product design with a prototype-first mindset , using early artifacts to test and learn. Bias to action —you plan for multiple iterations to move releases forward and reduce risk, not to seek perfection. Design systems thinking —ability to translate learnings into scalable design systems, patterns, and principles. Scaling quality through the team - coaching and leading designers, both in product, marketing, and external teams. Hands-on experience with AI-assisted design and prototyping tools , and curiosity to continuously explore new approaches.. Collaborative leadership style —you bring Product and Engineering along in the learning process. Cross platform experience, comfortable designing across web, desktop surfaces Submission Guidelines: Design Process: We value the rationale and methodology behind your work as much as the final visuals. When submitting your portfolio, please ensure it includes detailed insights into your design process, challenges addressed, and the results achieved. Leadership & Management: We are seeking a trustworthy, autonomous leader. In your resume, please provide a clear description of your managerial philosophy and your key achievements as a leader. Please note that applications that do not include the required materials/details above may not be eligible for further consideration. Benefits Visa and Relocation Our teams are working fully remotely, and we are expanding our global presence. While our headquarters are currently in Japan, relocation to Japan is not mandatory. If you wish to relocate, we are happy to help you obtain a visa. Working Arrangement Fully remote ※For employees residing near Tokyo, there may be opportunities to work in person several times a month Flexible working time Flexible time: 6:00 am - 11:30 am / 3:00 pm - 10:00 pm Core time: 11:30 am - 3:00 pm Virtual Office You'll have the ability to craft a character within a virtual office environment and engage with fellow colleagues through interactive experiences Others Home, or any other place equivalent to home ※There is a possibility of commuting to a location designated by the company due to business reasons 5-day workweek（Saturday, Sunday, Public Holidays / End of Year and New Year holidays (set by company) / others set by company） Full-time（Fixed overtime pay included） ※permanent employment 6 months Yes Additional Details to Follow During Hiring Process