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BoostDraft

MS Word-integrated legal document drafting tool

Head of Design

Full-TimeUpdated on 10/23/2026
No salary listed
Expert
Remote in Japan
Remote
Product & Experience DesignProduct Design

About the job

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.
  • Plan for multiple iterations to move releases forward and reduce risk rather than seeking perfection.
  • Apply design systems thinking to translate learnings into scalable design systems, patterns, and principles.
  • Coach and lead designers across product, marketing, and external teams.
  • Have hands-on experience with AI-assisted design and prototyping tools, and curiosity to continuously explore new approaches.
  • Use a collaborative leadership style that brings Product and Engineering into the learning process.
  • Have cross-platform experience designing across web and desktop surfaces.
  • Submit a portfolio that details the design process, methodology, challenges addressed, and results achieved.
  • Provide a clear description of managerial philosophy and key leadership achievements in the resume.
Responsibilities
  • Own and lead the user research practice, emphasizing early, prototype-driven user testing.
  • Use AI-assisted prototyping to 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 design philosophy and principles, including balancing speed with polish and AI-enabled workflows with traditional processes.
  • Ensure design decisions are grounded in evidence from real users.
  • Build, scale, and maintain a design system that encodes user insight and enables teams to move quickly with confidence.
  • Champion modern tools and workflows, especially AI, to reduce the cycle time from idea to prototype, user feedback, and 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 rather than long handoffs or static specifications.
  • Stay hands-on when needed by prototyping, testing flows with users, and unblocking high-impact work.
  • Work closely with Product and Engineering so learning velocity drives roadmap and prioritization.
  • Build shared understanding of users through prototypes, narratives, and clear synthesis.

About the company

BoostDraft is a tool that helps lawyers review, draft, and edit complex legal documents inside Microsoft Word. It works by integrating directly with Word to provide features like navigation, editing, proofreading, and auto-completion that suggests the correct section or defined term, so users don’t have to search for references or definitions. This seamless Word integration keeps documents consistent and secure while reducing manual minutiae and scrolling. Compared with other drafting tools, BoostDraft is differentiated by its tight Word integration and legal-focused features that streamline the drafting workflow rather than offering a general-purpose editor. The company’s goal is to give lawyers more time to focus on substantive legal work by speeding up document review and drafting and improving accuracy and consistency.

Company Size

11-50

Company Stage

N/A

Total Funding

N/A

Headquarters

San Francisco, California

Founded

2021

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Simplify Jobs

Simplify's Take

What believers are saying

  • BoostDraft launched Compare in 2025, expanding beyond drafting into file-version comparison.
  • Case studies show Silicon Legal Strategy saving 10% review time and Farella expanding usage.
  • February 2026 CEO Sean Yu and COO Haruku Horiuchi signal stronger global operating discipline.

What critics are saying

  • Microsoft or CLM suites can bundle similar Word-native review features by 2027.
  • Vendor fatigue is intense; legal buyers now compare four to twelve tools before choosing.
  • If BoostDraft cannot deepen integrations, workflow-native rivals will displace it in APAC and America.

What makes BoostDraft unique

  • BoostDraft lives inside Microsoft Word, reducing lawyer training and adoption friction.
  • Its product targets tedious review basics: cross-references, defined terms, formatting, and proofreading.
  • The January 2026 Actionstep partnership widens distribution into midsize law-firm workflows.

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Benefits

  • Remote Work Options
  • Flexible Work Hours

Growth & Insights and Company News

6 month growth

24%

1 year growth

24%

2 year growth

24%
BoostDraft
Mar 6th, 2026
5 things we heard at Future Contracts Miami 2026: interoperability, security, and the return of the basics.

5 things BoostDraft inc. heard at Future Contracts Miami 2026: interoperability, security, and the return of the basics. 03/06/2026 Introduction: A Maturing Conversation Around Contract Innovation The legal tech community gathered in Florida for Future Contracts Miami 2026, a fast-growing conference focused on the future of contract management, AI, and commercial legal operations. Hosted at the University of Miami, the event brought together hundreds of legal, procurement, and contract innovation professionals, with speakers and attendees representing organizations ranging from global enterprises to fast-growing startups. This year's conference featured insights from leaders across companies such as Airbus U.S., Royal Caribbean Group, UKG, and Ontop, alongside legal tech founders and operators building the next generation of contract tools. Discussions ranged from AI governance and vendor evaluation strategies to the evolving structure of the legal tech stack. For the BoostDraft team, the conversations were particularly illuminating - not just because of what was said on stage, but because of the discussions happening throughout the event floor. Across panels, booth conversations, and informal discussions with in-house counsel and legal operations professionals, several themes emerged about where contract technology is headed next. Below are five market signals that stood out most from Future Contracts Miami 2026, and what they suggest about the future of contract review and legal workflows. 1. Vendor Fatigue Is Real One theme came up repeatedly at the conference: the legal tech market has become crowded, and buyers are feeling it. Over the past few years, the explosion of AI-driven legal tools has dramatically expanded the contract technology landscape. While innovation has accelerated, many legal teams now find themselves evaluating multiple products that appear to solve similar problems. Several attendees described running pilots with four or five different tools simultaneously, while others reported reviewing as many as a dozen vendors before making a decision. This evaluation fatigue is becoming a real challenge for legal operations teams and general counsel. Even when a product solves a specific problem well, gaining internal approval for an additional tool can be difficult - especially when leadership is already investing heavily in contract lifecycle management (CLM) systems or AI drafting platforms. As a result, many conversations at the conference focused on consolidation and ecosystem partnerships. Legal teams increasingly want tools that integrate naturally with the rest of their contract workflows and tech stacks instead of forcing them to change how or where they work. 2. Security and AI Governance Are Rising to the Top of the Vendor Evaluation Checklist Another theme that surfaced repeatedly at Future Contracts Miami was the growing importance of security and governance in AI-enabled legal tools. Security has always been a key consideration for legal departments, particularly when evaluating tools that interact with sensitive contracts and confidential business information. But as AI capabilities become embedded in more legal software, many organizations are expanding their focus beyond traditional security measures to include how AI systems are managed, governed, and controlled. Several conference discussions highlighted that legal teams are increasingly asking deeper questions about AI-enabled tools: How is the technology trained? How is data handled? What safeguards are in place to ensure reliability and accountability? For many legal departments, these questions are no longer theoretical; they are becoming part of the standard procurement process. In practical terms, this means vendors must be able to clearly explain how their technology works, how it protects customer data, and how AI features are governed within their products. Transparency around these issues is becoming just as important as functionality. As AI adoption continues to accelerate across the legal profession, trust, governance, and security are quickly becoming key differentiators in the legal tech market. 3. Buying decisions are not just about technology. Another insight that emerged from conversations at the conference was that technology alone is rarely the deciding factor in vendor selection. In a market where many tools offer similar capabilities - particularly in areas like AI-assisted drafting, contract analytics, and workflow automation - buyers often find it difficult to distinguish between competing products based on features alone. As a result, legal teams increasingly evaluate vendors across a broader set of criteria. User experience, onboarding, customer support, and vendor relationships all play an important role in the decision-making process. When multiple tools appear capable of solving the same problem, factors such as intuitive design, ease of implementation, and responsive support can ultimately tip the balance. It's also increasingly common for legal teams to pilot several tools at once before making a final decision. These evaluations allow teams to see how a product performs in real-world workflows and whether it integrates smoothly into their existing processes. In a crowded legal tech market, the takeaway is clear: product experience and customer partnership can be just as important as technical capability when it comes to winning real adoption inside legal teams. 4. AI is expanding the tech stack...but also creating fragmentation. AI innovation is rapidly expanding what contract technology can do, but it is also creating a more complex technology landscape for legal teams to navigate. Rather than relying on a single, monolithic platform, many organizations are increasingly adopting specialized tools that address different layers of the contract workflow. Many conference attendees described contract processes that involve multiple technologies working together across stages such as intake and request management, drafting, review and analysis, and obligation management. In some cases, vendors are even forming partnerships to bridge these stages. One example discussed at the conference involved tools that handle the initial intake of legal requests and then route the work into a separate system designed for contract drafting or review. These kinds of integrations reflect an emerging reality: no single product currently solves every part of the contract lifecycle equally well. As a result, many organizations are building layered contract technology stacks, combining tools that each specialize in a specific part of the workflow. While this approach allows teams to take advantage of best-in-class capabilities, it also increases the importance of interoperability and seamless workflow integration between systems. 5. The basics of contract review are still key. One of the most interesting takeaways from conversations at the BoostDraft booth was how often attendees returned to a surprisingly simple point: many of the most time-consuming parts of contract review are still manual. While much of the legal tech conversation today focuses on AI-assisted drafting, contract analytics, and lifecycle management, many lawyers still spend a significant amount of time checking the fundamentals of a document. Tasks such as reviewing formatting, correcting spacing, resolving internal inconsistencies, and catching grammar or typographical errors remain a significant part of everyday contract work. For many legal teams - particularly those with small departments or solo reviewers - these operational details can consume a meaningful portion of the contract review process. Even experienced attorneys often find themselves manually scanning documents to catch errors or inconsistencies before a contract is finalized. The contrast between sophisticated AI drafting tools and these practical review tasks came up repeatedly. As contract technology becomes more advanced, many legal teams are still looking for ways to reduce the time spent on the operational mechanics of reviewing and cleaning up contracts. In other words, even in an era of rapid AI innovation, the fundamentals of contract review remain an important - and often underserved - part of a lawyer's deal workflow. What this means for the future of contract tech. Taken together, the conversations at Future Contracts Miami point to a legal tech market that is evolving quickly, but also becoming more pragmatic. The contract tech market is becoming more integrated, more security-focused, and more grounded in the realities of day-to-day legal work. The next phase of contract technology may not be about adding more AI. Instead, it may be about building tools that fit naturally into the day-to-day workflow of legal teams, helping them work faster, more accurately, and with greater confidence. If you're interested in seeing how BoostDraft helps legal teams streamline contract review directly inside Microsoft Word, book a demo and see how much time your team could save.

LawNext
Feb 5th, 2026
BoostDraft Appoints Sean Yu as CEO, Haruku Horiuchi as COO to Drive Global Growth

BoostDraft appoints Sean Yu as CEO, Haruku Horiuchi as COO to drive global growth. Tweet Share Share [San Francisco, California] - February 5, 2026 - BoostDraft, a leading provider of AI-assisted legal document automation solutions, today announced a new executive leadership structure to support its next phase of global growth. Effective January 31, 2026, Sean Yu has been appointed Chief Executive Officer, and Haruku Horiuchi has been appointed Chief Operating Officer. Yu succeeds the company's co-founders, Yohei Fujii and Hiroshi Watanabe, who will continue to support BoostDraft as founders and advisors. Founded in 2021, BoostDraft has established a strong presence across Japan, South Korea, and other APAC markets, while expanding rapidly in the United States, the United Kingdom, and other international markets. As demand grows for practical, workflow-native legal technology,the company is evolving its leadership structure to scale product development and operations globally. "BoostDraft has always been a product-first company, grounded in close collaboration with our customers," said Sean Yu, CEO of BoostDraft. "As we scale, my focus is on preserving that discipline - building reliable, intuitive tools that fit naturally into how lawyers already work, while expanding our ability to serve teams around the world." Yu brings extensive experience leading product growth at global technology companies including Wise, Skyscanner, and Alibaba. He joined BoostDraft in 2024 as Product Manager and has led product development during a period of rapid customer adoption. As COO, Haruku Horiuchi will oversee business operations and organizational scaling, translating product strategy into repeatable execution across the company's growing global footprint. "Scaling successfully requires more than just a strong vision. It requires systems that allow teams to execute consistently," said Haruku Horiuchi, COO of BoostDraft. "My role is to build the operational foundation that supports growth while preserving the culture and product quality that have defined BoostDraft from the beginning." Horiuchi previously held leadership roles at Yahoo Japan and Rakuten Group, where he managed large, multinational product organizations. He joined BoostDraft in 2025 as Senior Strategy and Business Operations Manager. About BoostDraft BoostDraft transforms Microsoft Word into an AI-assisted legal document editor, helping transactional lawyers automate tedious contract tasks such as checking internal cross-references, standardizing defined terms, and fixing formatting. With minimal training required and seamless integration into existing workflows, BoostDraft empowers legal teams to focus on the substance of business agreements instead of rote work. Learn more at boostdraft.com.

BoostDraft
Apr 15th, 2025
CLM vs. Contract Automation: What's the Difference?

BoostDraft, for example, integrates directly with Microsoft Word to automate rote review tasks and accelerate drafting, from running redlines between different document formats to checking defined terms - without requiring users to learn a new platform or change how they work.