We’re on a mission to help every family leave their legacy with a fast, easy, and secure way to create, manage, and distribute their estate plan online. Since 2017, we’ve helped hundreds of thousands of families plan for their future with a streamlined and intuitive approach that makes estate planning simple, affordable, and accessible. We’re backed by leading names in venture capital including Jackson Square Ventures, Link Ventures, Revolution’s Rise of the Rest, Halogen Ventures, and more.

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.
• 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 3+ 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.

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
• • 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: 

• We are a remote-first company, giving our employees the flexibility they need to work in an environment that best suits their needs. Our hiring process is also conducted virtually unless otherwise noted. We are a company that was founded in San Diego, CA, and offer a collaborative co-working space that is available for you to use if you'd like but not required. #LI-Remote
• We are proud to be a certified B Corporation, using business as a force for good. We are committed to building a healthy, sustainable, and engaging working environment for all employees, their families, and communities. We publish an annual impact report to outline our positive contributions to our world and set an example for all employers.
• Trust & Will's mission is to help every family leave their legacy through affordable, accessible estate planning. That starts with the people we hire and the ways in which we support the development of their unique talents and capabilities. We are committed to prioritizing ways to make our company and industry more inclusive. This means we must be revolutionary in the way we value diversity to revolutionize our business sector. At Trust & Will, everyone has a seat at the table and space to be their authentic selves because only in a company that is inclusive and diverse can we truly stand in our members' shoes.