Senior Product Designer (User Research & AI-Assisted Prototyping) at 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, the company has grown to 10,000+ paying users and earned adoption at 17 of Japan’s top 20 law firms—through word-of-mouth, profitability, and without external funding until January 2025.

Why you should join BoostDraft:

• Enjoy the entire process of achieving product-market fit and scaling the business.
• Learn from founders and management, leveraging Japan’s experience and product development insights.
• Work in an international environment with daily challenges.
• Interact with industry leaders focused on delivering exceptional user experiences.
• Use the latest technologies and bring your unique flair to the role.

Key Challenges:

Drive user insight through rapid exploration

• Own and lead user research with a bias toward early, prototype-driven testing.
• Use AI-assisted prototyping to explore ideas, validate assumptions, and identify risks before engineering investment.
• Convert ambiguous feedback and fragmented requests into clear hypotheses, prototypes, and actionable learnings.

Set the bar for product design

• Define and refine the design philosophy, balancing speed vs. polish and AI-enabled workflows vs. traditional processes.
• Ensure design decisions are evidence-based, grounded in real user insights—not opinions or hierarchy.

Make design a force multiplier

• Build, scale, and maintain a design system that encodes user insights and enables fast, confident teamwork.
• Champion modern tools and workflows—especially AI—to reduce cycle time from idea to prototype to user feedback to 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

• Collaborate closely 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.
• Bias to action—plan for multiple iterations to move releases forward and reduce risk, not 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 across 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 and desktop surfaces.

Submission Guidelines

• Design Process: Include detailed insights into your design process, challenges addressed, and results achieved in your portfolio.
• Leadership & Management: Provide a clear description of your managerial philosophy and key leadership achievements in your resume.

Applications without required materials may not be considered.

Benefits

Visa and Relocation: Fully remote teams with global expansion. Relocation to Japan is optional; we assist with visa support if desired.

Working Arrangement:

• Fully remote with flexible hours (6:00 AM–11:30 AM / 3:00 PM–10:00 PM) and a core time of 11:30 AM–3:00 PM.
• Virtual office environment with interactive colleague engagement.

Other Benefits:

• 5-day workweek (Saturday, Sunday, public holidays, and company-set holidays).
• Full-time position with fixed overtime pay and permanent employment.
• 6-month probation period.
• Prevention of passive smoking policy.