Head of Design

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' 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

Why Join Us?

Employee Benefits & Perks

Compensation : Salary + Equity

Our salary range for this position is $210,000 - $260,000, in addition to compensation we also include an employee equity package as a component of our offer along with other benefits and perks outlined below.

PTO

Flexible time off that you are encouraged to use; Generous paid company holidays and breaks throughout the year; Monthly friends & family days; Paid time off to volunteer in your community.

Health and Wellness Benefits

Fantastic health benefits including medical, dental, vision, life insurance, and generous parental leave; Financial wellness benefits (Equity & tax advisory support, savings options, and employee-sponsored 401k); Guest speakers & reimbursement for learning opportunities.

Extra

Flexible work schedule + hours; Family‑friendly work environment. We support the complexity of a remote world with the needs of families; Optional company‑sponsored events and travel throughout the year; $500 Work from home stipend + Apple accessories.

About Trust & Will

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