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Founded in 2017, Trust & Will is the leading digital estate planning platform trusted by over one million users. We provide modern, accessible solutions to help families protect their legacies with attorney‑approved, legally valid documents tailored to individual state requirements. Our seamless online platform simplifies the estate planning and settlement process, empowering individuals to create wills and trusts while also partnering with financial advisors, attorneys, and institutions to make legacy planning more inclusive and affordable.
About You
We are looking for an experienced and proven Head of Design to drive growth and innovation through our estate and wealth planning platform. You thrive on collaboration, creativity, and customer obsession, ensuring the experiences your team drives create real value. You will drive and execute our design strategy, ensuring it directly contributes to our business growth. As a key member of our Product, Design and Engineering leadership team, you will lead a team of Product Designers dedicated to understanding user problems, identifying unmet customer needs, and creating impactful solutions. You will work with Product and Engineering leadership to drive alignment, efficiency, and innovation, setting our teams up for success with clear objectives, streamlined processes, and the right tools to execute effectively.
About the Role
- Define and drive the overall design strategy to align with our customer needs and business outcomes.
- Lead and mentor a team of Product Designers, fostering a culture of curiosity, collaboration, and continuous improvement.
- Balance creating delightful customer experiences with the company's business outcomes.
- Oversee the end-to-end design process, ensuring a customer-centered approach in problem-solving, solution ideation, and product development.
- Collaborate closely with Product and Engineering to prioritize, scope, and execute initiatives that drive measurable customer and business impact.
- Implement and refine design processes to ensure efficient workflows, strong cross‑functional communication, and high‑quality execution.
- Develop and maintain a scalable and delightful design system that enhances usability and maintains brand consistency.
- Advocate for user experience excellence across all touchpoints, balancing business goals with customer delight.
- Utilize data‑driven insights and user research to inform design decisions and validate product direction.
- Stay ahead of industry trends, emerging technologies, and best practices to drive continuous innovation, especially as Generative AI becomes more commonplace in research and design practices.
Qualifications
- 8+ years of experience in UX/Product Design, with at least 5+ years in a leadership role.
- Proven experience leading design teams in a fast-paced, tech‑driven environment.
- Strong portfolio showcasing a history of solving complex user problems and delivering impactful products.
- Deep expertise in user research, interaction design, information architecture, and visual design.
- Strong leadership skills, with the ability to coach, mentor, and inspire designers at all levels.
- Experience working closely with Product and Engineering teams to drive alignment and execution.
- Excellent communication skills, with the ability to present design concepts and rationale to stakeholders at all levels.
- Proficiency in design tools (e.g., Figma, Sketch, Adobe Creative Suite) and familiarity with Agile methodologies.
- Ability to think strategically while maintaining a hands‑on approach to problem‑solving.
- Residence in one of the following states: CA, CO, FL, GA, ID, IL, MD, NJ, NY, NC, SC, PA, TX, VT.
Why Join Us
- Opportunity to lead and shape the design function at a growing tech startup.
- Collaborative and dynamic work environment with a strong culture of innovation.
- Competitive salary, equity options, and comprehensive benefits package.
- A chance to make a real impact by creating products that solve meaningful customer problems.
Employee Benefits & Perks
- Compensation: Salary + Equity – $210,000‑$260,000 plus equity package.
- PTO – Flexible time off, generous paid holidays, monthly friends & family days, volunteer PTO.
- Health and Wellness Benefits – Medical, dental, vision, life insurance, parental leave, 401(k), equity & tax advisory support, learning reimbursement.
- Extra – Flexible work schedule, family‑friendly environment, optional company events, $500 work‑from‑home stipend + Apple accessories.
About Trust & Will
- Remote‑first company offering flexibility for all employees.
- B Corporation committed to building a healthy, sustainable, and engaging workplace.
- Mission: to help every family leave their legacy through affordable, accessible estate planning.
- Privacy Notice: Trust & Will collects personal information from applicants to evaluate qualifications and communicate about your application. California residents have the right to know what information we collect, request a copy, correct inaccuracies, or request deletion.