About the Role
As a Senior Product Designer at DraftWise, you will be primarily responsible for the design quality and intuitive flow of our core product experiences inside Microsoft Word. Lawyers are a demanding user base, so our product must be engaging, simple, and learnable in minutes while still handling complex drafting, review, negotiation, and search workflows. You will help raise the design standard across the product, contribute to evolving our design system, and partner closely with Product, Customer Success, Engineering, and our AI teams as we ship new capabilities for lawyers.
A big part of the role is designing AI powered experiences that lawyers can trust and control. You will craft interfaces that help users understand what the system is doing, guide outputs effectively, and iterate safely, with the right balance of automation and human judgment. You will also be AI enabled in your own practice, using modern AI tools to accelerate exploration, research synthesis, prototyping, and iteration while maintaining high craft and strong product judgment.
You will conduct user research directly with lawyers, build and iterate on prototypes, deliver polished screens and interaction specs to engineering, and validate that your designs drive real improvements in adoption, satisfaction, and workflow efficiency.
We are quickly growing the number of lawyers on the platform and need DraftWise to be compelling, valuable, and enjoyable to use. We can only do that with your help.
We are a small team and expect everyone to flex to what the company needs most. If you see an opportunity to make DraftWise better, we want to empower you to pursue it. You will have broad ownership over your initiatives, real influence on our culture as we grow, and the chance to lead key efforts that put our technology in the hands of lawyers.
What we value:
- Strong communication in an open and collaborative environment.
- Creating trust through thoughtful, well intentioned feedback.
- High ownership, independence, and comfort making decisions with minimal supervision.
- Comfort operating in a dynamic environment with shifting priorities.
- A high bar for craft and clarity, where every detail matters and every interaction earns its place.
About You
We're looking for employees who have:
- We are looking for someone who has
- Exceptional communication skills with an emphasis on building trust across functions.
- Passion for customer outcomes and a desire to see lawyers succeed with what you build.
- 3 plus years of product design experience on production B2B software with real users.
- Experience collaborating closely with product, engineering, customer teams, and founders, synthesizing multiple perspectives into a clear direction.
- Proven end to end design process skills, including research, prototyping, iteration, and post release validation.
- Strong UI and interaction design craft, with an instinct for simplicity and polish.
- AI enabled, comfortable using AI tools in your workflow, and good judgment about how to design AI features that users can understand, guide, and trust.
- Proficiency with Figma or similar design and prototyping tools.
What we offer
- All-remote work style, work anywhere. Ideally within UTC+4 to UTC-7
- Equity plan
- Competitive salary
- Private medical care
- New laptop and a work-from-home stipend for necessary accessories
- Generous PTO / sick leave
- Opportunity to lead our company as we disrupt the legal world
π Y Combinator Company Info
Y Combinator Batch: S20
Team Size: 50 employees
Industry: B2B Software and Services -> Legal
Company Description: Contract and negotiation AI built for lawyers
π° Compensation
Salary Range: $70,000 - $90,000
π Job Details
Job Type: Full-time
Experience Level: 3+ years
Design Type: UI / UX
Time to Hire: 14
π― Interview Process
- Intro Chat: We want to share with you what we are building and to learn more about your interests and experience. We are searching for enthusiasm, ownership and autonomy. We'd love to see an example of a project you've worked on. (30 mins)
- Case Study Discussion: We'll share a user need and some background context and we'll ask you to walk us through your user research process (45 mins)
- Take-Home Project: We'll share a set of features that we need to incorporate into a new search page and we ask that you spend a small amount of time producing a design for this new search page (<2 hours)
We would also love for you to meet the team! We have excellent people working here and we want to help you feel welcome before making your decision.
The typical interview process takes 2 weeks from start to finish.