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About the Role

BoostDraft is reinventing legal drafting with a local Microsoft Word add-in that automates tedious formatting and elevates lawyers’ day-to-day work. You can enjoy the whole process of product market fit, and scale the business. You will use the latest technologies and will be encouraged to bring your flair to the role.

Responsibilities

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.
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.
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 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.
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

Portfolio must include detailed insights into your design process, challenges addressed, and the results achieved.
Resume must provide a clear description of your managerial philosophy and your key achievements as a leader.
Applications that do not include the required materials/details may not be eligible for further consideration.
During online interviews, the use of both camera and microphone is mandatory.
If suspicious behavior is detected, you may be asked to disable video filters or perform a simple on-screen action.
If you are unable or unwilling to comply with requests during an interview, 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.

Skills

Qualitative user research, especially concept testing, usability testing, and workflow validation
Leading product design with a prototype-first mindset, using early artifacts to test and learn
Bias to action—plan for multiple iterations to move releases forward and reduce risk
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—bring Product and Engineering along in the learning process
Cross platform experience, comfortable designing across web, desktop surfaces

Location

Fully remote
Near Tokyo (potential for in-person work)

Work Type

Fully remote
Flexible working time
Full-time
Permanent employment

Experience Level

6 months (probationary period)

Benefits

Virtual office environment with interactive experiences

About the Company

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.
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.

Equal Opportunity

We are committed to providing a fair and secure hiring process for all candidates.
These measures are applied equally to all candidates to ensure a trustworthy and fair hiring environment.