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.

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 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.

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.

Design systems thinking—ability to translate learnings into scalable design systems, patterns, and principles.

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.

Bias to action—you plan for multiple iterations to move releases forward and reduce risk, not to seek perfection

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 fellows