Head of Design / Principal Designer

BoostDraft Job Opportunity 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.
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 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.
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