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Senior Product Designer II, Professionals

Trust & Will Remote (πŸ‡ΊπŸ‡Έ United States of America)

Remote $175,000 - $200,000 Full-time Senior

Lead the end-to-end design of complex B2B platform products for financial advisors, attorneys, and nonprofit partners. Collaborate with Product and Engineering squads to translate research and behavioral data into high-quality, AI-enhanced user experiences.

Responsibilities

  • Start with the right problem, doing the work of understanding what actually needs solving through research and turning it into a point of view that the team can build toward
  • Shape what gets prioritized, working closely with PMs to influence the roadmap
  • Own complex, multi-sided design problems end-to-end, designing for the tension between advisors and clients
  • Set the craft bar, bringing a sophisticated visual design sensibility to the product
  • Move fast and know when to slow down, making smart tradeoffs with Product and Engineering
  • Use AI as a design tool and a design medium, integrating AI tools into your workflow and designing AI-powered features
  • Contribute to systems, helping extend the design system in ways that scale
  • Raise the bar for the team around you, bringing a point of view on where design is headed and sharing thinking to elevate the team

Requirements

  • 7+ years in product design with a portfolio that demonstrates strong visual craft, clear design thinking, and shipped work across web and mobile - AI-powered experiences included
  • Proven experience on B2B or platform products with multiple, distinct user types
  • Ability to work 0-to-1, the level of new product areas or audience segments
  • Hands-on fluency with AI tools in your actual workflow - show us how you use them
  • Fluency in Figma; meaningful experience contributing to or owning a design system
  • Track record of shipping high-quality work on time with edge cases considered - you catch what others miss
  • Strong communicator who can advocate for design decisions with PMs, engineers, and business stakeholders
  • Experience working in a high-growth startup and/or fintech or regulated consumer product β€” this space carries real stakes for real families and you take that seriously

Benefits

  • Salary + Equity
  • Flexible time off that you are encouraged to use
  • Generous paid company holidays and breaks throughout the year
  • Monthly friends & family day
  • Paid time off to volunteer in your community
  • Exceptional health benefits including medical, dental, vision, life, and disability insurance
  • Mental health support through Spring Health, plus access to One Medical for primary care and Cleo for family planning and caregiving
  • Financial wellness benefits (unlimited 1:1 sessions with a UBS financial coach and employer-sponsored 401k with up to 4% company match)
  • Extra Flexible work schedule + hours
  • Family-friendly work environment
  • Up to $1,000 annually in learning & development reimbursement
  • Optional company-sponsored events and travel throughout the year
  • $500 Work from home stipend + Apple accessories

Key Skills

Product design Visual design AI-powered design Figma Design systems Communication skills Collaboration skills Problem-solving skills User research User experience (UX) design B2B or platform products Hands-on fluency with AI tools Strong visual craft Clear design thinking Shipped work across web and mobile AI-powered experiences Multi-sided design problems Sophisticated visual design sensibility Scalable design systems Design leadership Influence on product roadmap Tradeoffs with Product and Engineering Cross-functional collaboration Agile methodologies Design thinking User-centered design Wireframing Prototyping Usability testing A/B testing Data analysis Research synthesis Concept generation Rapid prototyping

About Trust & Will

Founded in 2017, Trust & Will is the leading digital estate planning platform in the U.S., trusted by over one million individuals and families. Our simple, secure, and attorney-approved online solutions help Americans create wills, trusts, healthcare directives, and other essential estate planning documents tailored to state-specific laws. With a focus on accessibility and a guided experience, we’re transforming how families plan for the future and protect their legacies. In 2025, we launched EstateOSβ„’, the first intelligent platform built to modernize how legacies are planned, managed, and preserved. EstateOS powers dynamic, connected estate plans for families, and introduces AI-enabled workflows, document intelligence, and multi-party collaboration tools for professionals. Our platform supports over 20,000 financial advisors and 200+ enterprise partners and institutions β€” including AARP, Fifth Third Bank, LPL Financial, UBS, and USAA. By integrating estate planning into client ser

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