Head of Design

About the role

BoostDraft is a legal drafting tool built as a Microsoft Word add-in, founded by MIT and Stanford alumni and now used by more than 10,000 paying users, including 17 of Japan's top 20 law firms. It is looking for a Head of Design to drive user insight, define its design philosophy and lead a team of product designers. The role is full-time and fully remote, with flexible hours and a 6-month probation period.

Key responsibilities

• Own and lead the user research practice, with a focus on early, prototype-driven testing and AI-assisted prototyping to validate assumptions before engineering investment.
• Turn ambiguous feedback into clear hypotheses, prototypes and learnings that guide product direction.
• Define and evolve the design philosophy and principles, balancing speed versus polish and AI-enabled workflows versus traditional ones, and ground design decisions in evidence from real users.
• Build, scale and maintain a design system, and champion modern tools and workflows, especially AI, that shorten the cycle from idea to decision.
• Lead and coach a team of product designers, setting expectations that learning comes from making, testing and iterating rather than long handoffs.
• Partner closely with Product and Engineering so that learning velocity drives roadmap and prioritization, and help the organization share a common understanding of users through prototypes and narratives.

Required profile

• Fluency in qualitative user research, especially concept testing, usability testing and workflow validation.
• Strong experience leading product design with a prototype-first mindset, planning for multiple iterations to reduce risk.
• Ability to turn learnings into scalable design systems, patterns and principles, and to coach designers across product, marketing and external teams.
• Hands-on experience with AI-assisted design and prototyping tools, and a collaborative leadership style.
• Cross-platform experience, comfortable designing across web and desktop surfaces.

What we offer

• Fully remote work, with possible in-person days for those living near Tokyo.
• Flexible working hours (6:00-11:30 and 3:00-10:00, core 11:30-15:00) and a 5-day workweek.
• A virtual office environment and visa and relocation support for those wishing to move to Japan.
• Permanent employment with fixed overtime pay and a 6-month probation period.