Senior Product Designer II, Professionals

📍 Job Overview

Job Title: Senior Product Designer II, Professionals

Company: Trust & Will

Location: United States

Job Type: Full-Time

Category: Product Design / UX/UI

Date Posted: May 20, 2026

Experience Level: Mid-Senior Level (7+ years)

Remote Status: Remote OK

🚀 Role Summary

• Lead end-to-end product design for complex B2B and platform products, focusing on the Professionals channel within the estate planning domain.

• Drive product strategy and roadmap influence by synthesizing user research, behavioral data, and market trends into actionable design points of view.

• Develop sophisticated visual design and interaction patterns for a professional user base, balancing functionality with a high-craft aesthetic to build trust.

• Integrate AI tools into the design process for research, concept generation, and prototyping, while also designing AI-powered features with a focus on user trust and helpfulness.

• Collaborate closely with Product Management and Engineering teams in a high-autonomy, fast-paced startup environment to deliver high-quality, impactful user experiences.

📝 Enhancement Note: This role is specifically for a Senior Product Designer focusing on the "Professionals" segment of Trust & Will's platform, which serves financial advisors, attorneys, and nonprofit partners. This implies a need for expertise in B2B or platform design, an understanding of professional user workflows, and the ability to design for a multi-sided market (professionals and their clients). The emphasis on AI integration suggests a forward-thinking approach to design tools and product features.

📈 Primary Responsibilities

• Conduct comprehensive user research, including interviews and behavioral data analysis, to deeply understand the needs and pain points of financial advisors, attorneys, and nonprofit partners.

• Translate research findings and strategic objectives into compelling design solutions, defining problems and proposing user-centric approaches before detailed design work begins.

• Collaborate with Product Managers to influence the product roadmap, ensuring user needs and design perspectives are incorporated into strategic prioritization.

• Own the complete design lifecycle for complex, multi-sided features, considering the distinct needs and interactions of both professional users and their end-clients.

• Develop and advocate for sophisticated visual design, typography, color, and motion to create an intuitive and trustworthy user experience that resonates with financial professionals.

• Set and maintain a high standard for design craft, interaction patterns, and overall product aesthetics, moving beyond a purely functional design approach.

• Make informed, rapid design decisions and smart tradeoffs with Product and Engineering teams, balancing scope, effort, and opportunity cost in a startup environment.

• Leverage AI tools for research synthesis, concept generation, and rapid prototyping, and design AI-powered features that are trustworthy, helpful, and meet user expectations.

• Contribute to and extend the company's design system, developing reusable patterns that ensure scalability and consistency across the Professionals platform and other product areas.

• Elevate the design team's capabilities by sharing insights on design trends, facilitating critiques, and fostering a collaborative environment that encourages continuous learning and improvement in craft and process.

📝 Enhancement Note: The responsibilities highlight a significant emphasis on research synthesis, strategic influence, and end-to-end ownership of complex, multi-sided problems. The requirement to "set the craft bar" and integrate AI suggests a role that is both strategic and execution-focused, with a strong emphasis on high-quality visual and interaction design.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong portfolio demonstrating equivalent experience and expertise in product design is paramount.

Experience: 7+ years of professional experience in product design, with a proven track record of shipping impactful B2B or platform products.

Required Skills:

• Product Design Leadership: Demonstrated ability to lead complex design initiatives from concept to launch, with a strong portfolio showcasing shipped work.

• B2B/Platform Design Expertise: Proven experience designing for products with multiple, distinct user types and complex workflows, particularly in B2B or platform environments.

• User Research & Synthesis: Proficient in conducting user interviews, analyzing behavioral data, and synthesizing findings into clear, actionable design strategies and points of view.

• Visual & Interaction Design: Strong visual design sensibility, with fluency in hierarchy, typography, color, and motion, and the ability to create sophisticated and trustworthy user interfaces.

• Figma Proficiency: Expert-level skills in Figma for design, prototyping, and collaboration.

• Design Systems: Meaningful experience contributing to or owning a design system, with the ability to create scalable and reusable design patterns.

• AI Tool Integration: Hands-on fluency with AI tools in the design workflow (e.g., for research synthesis, concept generation, prototyping) and the ability to design AI-powered features.

• Communication & Influence: Excellent communication skills, with the ability to articulate design rationale, advocate for design decisions, and influence stakeholders (PMs, engineers, business leaders).

• Problem Solving (0-to-1): Ability to navigate ambiguity and define new product areas or audience segments from scratch.

• Attention to Detail: A track record of shipping high-quality work that considers edge cases and demonstrates meticulous attention to detail.

Preferred Skills:

• Fintech/Regulated Product Experience: Experience working within the fintech sector or with regulated consumer products, demonstrating an understanding of the stakes involved.

• Startup Environment Acumen: Experience thriving in a high-growth startup environment, characterized by rapid iteration and adaptability.

• Web & Mobile Design: Experience designing across both web and mobile platforms.

• Prototyping: Advanced prototyping skills to effectively communicate complex interactions and user flows.

📝 Enhancement Note: The emphasis on "7+ years" and the specific mention of "0-to-1" ability suggests this role is for a senior individual contributor who can operate with significant autonomy and drive new product initiatives. The requirement for hands-on AI tool usage is a critical differentiator.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrated B2B/Platform Design: Showcase case studies of complex B2B or platform products with multiple user types, clearly outlining the problem, your role, the design process, and the impact.

• End-to-End Ownership: Present projects that illustrate your ability to take ownership from initial research and problem definition through to final shipped product.

• Visual Craft & Interaction Design: Highlight sophisticated visual design, including clear hierarchy, typography, and interaction patterns that build trust and usability.

• AI Integration Examples: Include examples or discussions of how you've integrated AI tools into your design process or designed AI-powered features, detailing the benefits and challenges.

• Design System Contributions: If applicable, showcase contributions to or ownership of design systems, demonstrating how you build scalable and reusable patterns.

• Impact & Metrics: Quantify the impact of your design work using relevant metrics (e.g., user adoption, efficiency gains, conversion rates, client satisfaction) where possible.

Process Documentation:

• Research Synthesis: Portfolios should demonstrate strong synthesis skills, showing how raw research data (interviews, analytics) was transformed into actionable design insights and strategies.

• Workflow Optimization: Case studies should illustrate how you've optimized workflows for professional users, considering efficiency, usability, and the integration of their clients' needs.

• Systematic Design: Evidence of designing with a systems-thinking approach, contributing to or leveraging design systems for consistency and scalability.

📝 Enhancement Note: The portfolio requirements are critical for this role. Emphasis is placed on demonstrating experience with complex B2B/platform products, end-to-end ownership, high-craft visual design, and practical application of AI tools within the design process. Quantifiable impact is also highly valued.

💵 Compensation & Benefits

Salary Range: $175,000 - $200,000 USD per year.

Benefits:

• Compensation: Competitive salary plus an employee equity package.

• Paid Time Off (PTO):

  • Flexible time off policy, encouraging usage.
  • Generous paid company holidays and breaks.
  • Monthly friends & family day.
  • Paid time off for community volunteering.

• Health and Wellness:

  • Comprehensive health benefits: medical, dental, vision, life, and disability insurance.
  • 100% premium coverage for employees and dependents on medical plans.
  • Mental health support via Spring Health.
  • Access to One Medical for primary care.
  • Family planning and caregiving support through Cleo.

• Financial Wellness:

  • Unlimited 1:1 sessions with a UBS financial coach.
  • Employer-sponsored 401k with up to a 4% company match.

• Work Flexibility & Support:

  • Flexible work schedule and hours.
  • Family-friendly work environment.
  • $500 Work From Home stipend.
  • Apple accessories provided.

• Professional Development:

  • Up to $1,000 annually for learning & development reimbursement.

• Other Perks:

  • Optional company-sponsored events and travel. Working Hours: Flexible work schedule and hours, with an assumed standard of 40 hours per week.

📝 Enhancement Note: The salary range is clearly defined. The benefits package is extensive, with a strong emphasis on comprehensive health coverage (100% premium for employees/dependents), mental and family wellness support, financial planning resources, and significant flexibility and stipends for remote work. The "Equity" benefit is also notable for a senior role.

🎯 Team & Company Context

🏢 Company Culture

Industry: Legal Tech / Fintech / Estate Planning

Company Size: The description implies a growth-stage company that has scaled significantly (over one million users), likely falling into the 50-250 or 251-500 employee range based on typical startup growth trajectories.

Founded: 2017, indicating a relatively young but established company with a strong market presence.

Team Structure:

• The role is embedded within the "Professionals squad," which is noted as the fastest-growing part of the business. This suggests a dedicated, cross-functional team focused on this specific market segment.

• The Senior Product Designer II will work closely with Product Managers and Engineers within this squad, indicating a collaborative, agile team structure.

Methodology:

• Data-Driven Design: Emphasis on using research, behavioral data, and market analysis to inform design decisions and define problems.

• User-Centricity: A core focus on understanding and serving the needs of both professionals and their clients.

• Agile Development: Working in a startup pace, making smart tradeoffs with Product and Engineering, points to an agile or lean development methodology.

• AI Integration: Proactive adoption and integration of AI tools into both the design process and the product itself.

• Design Systems: Commitment to building scalable and reusable design patterns through a design system.

Company Website: https://trustandwill.com/

📝 Enhancement Note: Trust & Will positions itself as a leader in digital estate planning, leveraging technology to make a complex process accessible. The company is a certified B Corporation, signaling a commitment to social and environmental responsibility alongside profit. The culture appears to value innovation (AI), user empathy, and a data-driven approach, within a fast-paced, collaborative startup environment.

📈 Career & Growth Analysis

Operations Career Level: This is a Senior Product Designer II role, signifying a mid-to-senior level individual contributor position. It requires substantial experience (7+ years) and the ability to operate with high autonomy, lead complex design problems end-to-end, and influence product strategy. It's a key role within the design function, expected to not only execute but also elevate the team's craft and process.

Reporting Structure: The Senior Product Designer II will be embedded within the "Professionals squad," working closely with Product Managers and Engineers. They will likely report to a Design Lead, Head of Product Design, or potentially a Group Product Manager, depending on the specific organizational structure.

Operations Impact: The work directly impacts the Professionals channel, which is described as the "fastest-growing part of our business" and "one of the most consequential." The designs will shape how financial advisors, attorneys, and nonprofit partners serve millions of families, influencing Trust & Will's market penetration, user trust, and overall revenue growth in this critical segment. The role is crucial for driving adoption and retention among professional users.

Growth Opportunities:

• Leadership in Design: Potential to grow into a Design Lead or Principal Designer role, taking on more strategic oversight and mentoring junior designers.

• Specialization: Deepen expertise in B2B platform design, AI-driven product experiences, or specific areas within fintech/legal tech.

• Cross-Functional Influence: Expand influence across product areas and contribute to broader company strategy as the company scales.

• Skill Development: Utilize the $1,000 annual L&D reimbursement for courses, conferences, or certifications to enhance skills in areas like AI in design, advanced UX research, or strategic product thinking.

• Impactful Projects: Opportunity to lead design for high-impact, high-visibility features in a rapidly growing segment of the business.

📝 Enhancement Note: This role offers significant autonomy and the chance to make a tangible impact on a growing business segment. Growth opportunities are geared towards deepening design leadership, strategic contribution, and specialized skill development, fitting for a senior individual contributor path.

🌐 Work Environment

Office Type: Trust & Will is a "remote-first company." They offer a collaborative co-working space in San Diego, CA, which is available for use but not required. This indicates a hybrid-friendly approach for those in proximity to the office, but a fully remote setup is the primary model.

Office Location(s): Primarily remote, with a co-working space available in San Diego, California. The role is restricted to candidates residing in specific US states (CA, CO, FL, GA, ID, IL, MD, NJ, NY, NC, PA, TX, VT, NV, UT).

Workspace Context:

• Remote Flexibility: Employees have the flexibility to work in an environment that best suits their needs, a key aspect of a remote-first culture.

• Technology & Tools: Access to necessary tools and technology, including a $500 Work From Home stipend and Apple accessories, to ensure a productive remote setup.

• Collaboration: While remote, the emphasis on cross-functional squads and virtual collaboration tools suggests an environment designed for effective remote teamwork. Company-sponsored events and travel may also facilitate in-person connections.

Work Schedule: Flexible work schedule and hours are offered. While a standard 40-hour work week is implied, the flexibility allows for better work-life integration, which is particularly beneficial for managing complex design projects and personal needs.

📝 Enhancement Note: The remote-first nature, coupled with specific state residency requirements, defines the primary work environment. The company supports remote work with stipends and tools, while also offering optional in-person collaboration opportunities.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your resume and portfolio by the recruiting team to assess fit with the role's requirements, especially B2B/platform experience and AI tool usage.

• Portfolio Presentation & Design Exercise: A likely step where candidates present their portfolio, discussing case studies, their design process, and how they've handled complex problems. This may be combined with or followed by a design challenge or exercise, potentially focused on a B2B scenario or AI integration.

• Hiring Manager/Team Interviews: Interviews with the hiring manager (likely a Design Lead or Head of Design) and cross-functional team members (PM, Engineering) to assess design thinking, collaboration skills, communication, and cultural fit.

• Final Interview: Potentially a final interview with senior leadership to discuss strategic alignment and overall fit.

Portfolio Review Tips:

• Curate Strategically: Select 3-4 strong case studies that best showcase your experience with complex B2B/platform products, end-to-end design ownership, sophisticated visual craft, and AI integration.

• Structure for Clarity: For each case study, clearly articulate:

  • The Problem: What was the user or business challenge?
  • Your Role: Specifically what you did.
  • The Process: Your research, ideation, iteration, and design decisions.
  • The Solution: Key screens, flows, and design rationale.
  • The Impact: Quantifiable results (metrics) or qualitative outcomes.

• Highlight AI Usage: Explicitly detail how you used AI tools in your workflow or designed AI-powered features. Discuss the tools, the outcomes, and any learnings.

• Showcase Visual Craft: Ensure your portfolio reflects a high standard of visual design, typography, and interaction.

• Articulate Tradeoffs: Be prepared to discuss the difficult decisions and tradeoffs you made during the design process.

Challenge Preparation:

• Understand the Domain: Familiarize yourself with Trust & Will's mission, the estate planning industry, and the needs of financial advisors, attorneys, and nonprofit partners.

• B2B/Platform Mindset: Practice thinking about user needs in a professional context – efficiency, trust, client impact, and integration into existing workflows.

• AI Application: Consider potential AI applications within estate planning for professionals and how you would design those experiences.

• Communication: Practice clearly articulating your thought process, design decisions, and rationale under pressure.

📝 Enhancement Note: The emphasis on a portfolio review and potential design challenge suggests a strong focus on practical design skills and the ability to articulate design thinking. Candidates should be prepared to demonstrate their experience with B2B/platform products and AI tools specifically.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma (required, expert fluency), potentially other tools for rapid prototyping or specific workflows.

• Design Systems: Experience with contributing to or managing design systems is crucial.

• AI Tools: Hands-on fluency with AI tools for design (e.g., Midjourney, Stable Diffusion for ideation, AI-powered research synthesis tools, AI coding assistants for prototyping).

Analytics & Reporting:

• Familiarity with analytics platforms (e.g., Google Analytics, Mixpanel, Amplitude) to understand user behavior and measure design impact.

CRM & Automation:

• While not a direct requirement for a Product Designer, understanding the CRM landscape (e.g., Salesforce, HubSpot) and how design impacts B2B sales and customer success workflows can be beneficial.

• Familiarity with project management tools (e.g., Jira, Asana) for collaboration with engineering teams.

📝 Enhancement Note: Figma is explicitly called out as a required tool. A strong emphasis is placed on AI tool proficiency within the design workflow. Experience with design systems is also a key technical requirement.

👥 Team Culture & Values

Operations Values:

• Mission-Driven: A strong commitment to the company's mission of making estate planning accessible and protecting families' legacies. This is a core motivator.

• User Empathy: Deep understanding and care for the needs of both professional users and the families they serve.

• Collaboration & Influence: Working effectively with cross-functional teams, influencing decisions with strong design rationale, and contributing positively to team dynamics.

• Craftsmanship & Quality: A dedication to high-quality design, attention to detail, and continuous improvement in design execution.

• Innovation & Adaptability: Embracing new technologies like AI and thriving in a fast-paced, evolving startup environment.

• Integrity & Trust: Essential in the estate planning and financial services space, reflected in the design of trustworthy and reliable products.

Collaboration Style:

• Cross-Functional Integration: Seamless collaboration with Product Managers and Engineers within the Professionals squad, involving them early and often in the design process.

• Open Critique & Feedback: A culture that encourages constructive critique and feedback exchange to elevate design quality and team learning.

• Data-Informed: Collaborating with data analysts and PMs to ensure design decisions are backed by user data and business objectives.

• Proactive Communication: Maintaining clear and consistent communication, especially in a remote-first environment, to ensure alignment and shared understanding.

📝 Enhancement Note: The company culture is strongly tied to its mission and values, emphasizing empathy, integrity, and a commitment to using business as a force for good (B Corp). The collaborative style is geared towards agile, cross-functional teamwork in a remote setting.

⚡ Challenges & Growth Opportunities

Challenges:

• Designing for Multi-Sided Markets: Balancing the distinct needs and priorities of financial advisors/attorneys and their end-clients within a single platform.

• Building Trust in a Regulated Space: Designing for an industry where trust, accuracy, and legal compliance are paramount, especially when introducing new technologies like AI.

• Navigating Ambiguity (0-to-1): Taking ownership of new product areas or audience segments where the problem space may not be fully defined.

• Elevating Craft: Raising the visual and interaction design bar in a product that may have historically leaned functional, ensuring it meets the expectations of sophisticated professional users.

• AI Integration Nuances: Effectively incorporating AI into user workflows and product features in a way that is genuinely helpful, trustworthy, and avoids potential pitfalls or user distrust.

• Startup Pace: Adapting to the fast-paced, iterative nature of a high-growth startup, making smart tradeoffs while maintaining quality.

Learning & Development Opportunities:

• AI in Design Mastery: Deepen expertise in leveraging AI tools for design research, generation, and prototyping, potentially becoming a go-to resource for the team.

• B2B Platform Design Leadership: Gain extensive experience and recognition for designing complex, successful B2B platforms.

• Strategic Product Influence: Develop skills in shaping product roadmaps and influencing business strategy through design insights.

• Mentorship: Opportunity to mentor junior designers and contribute to the growth of the design team.

• Industry Best Practices: Stay at the forefront of design trends, particularly in fintech, legal tech, and AI-driven product development, potentially through the L&D reimbursement.

📝 Enhancement Note: The challenges are directly related to the complexities of the role: multi-sided markets, regulated industries, AI integration, and startup dynamics. Growth opportunities align with advancing design leadership and strategic impact.

💡 Interview Preparation

Strategy Questions:

• "Tell me about a complex B2B or platform product you designed end-to-end. What were the unique challenges, and how did you address them?" (Focus on your process, user research synthesis, and stakeholder management.)

• "Describe a time you had to influence a product roadmap or advocate for a design decision against strong opinions. How did you build your case and what was the outcome?" (Highlight your communication, rationale, and ability to make tradeoffs.)

• "How have you integrated AI tools into your design workflow? Can you walk me through a specific example of how it improved your process or the final product?" (Be ready to demonstrate hands-on experience and critical thinking about AI's role.)

Company & Culture Questions:

• "What interests you about Trust & Will's mission, and how does that connect with your own values?" (Research the B Corp status, mission, and recent company news.)

• "How do you approach collaborating with Product Managers and Engineers in a remote, fast-paced environment?" (Emphasize proactive communication, empathy, and shared ownership.)

Portfolio Presentation Strategy:

• Tell a Story: For each case study, frame it as a narrative: the challenge, your journey, the solution, and the impact.

• Focus on Rationale: Emphasize why you made certain design decisions, linking them back to user needs, business goals, and constraints.

• Show, Don't Just Tell: Use visuals effectively, but be prepared to articulate the nuances of user flows, interaction patterns, and visual hierarchy.

• Quantify Impact: Where possible, use data and metrics to demonstrate the success of your designs.

• Be Honest About Tradeoffs: Discuss the limitations, challenges, and decisions made under pressure. This shows maturity and realistic problem-solving.

• AI Integration Focus: Dedicate a portion of your presentation to showcasing your AI tool usage and its impact.

📝 Enhancement Note: Interview preparation advice focuses on demonstrating core competencies: B2B/platform design, AI integration, strategic influence, and strong communication skills, all within the context of Trust & Will's mission and culture.

📌 Application Steps

To apply for this Senior Product Designer II position:

• Submit your application through the Trust & Will careers portal (linked via Greenhouse).

• Portfolio Customization: Tailor your resume and portfolio to highlight your 7+ years of experience in B2B/platform design, your fluency with Figma, and specific examples of how you've used AI tools in your design workflow. Showcase end-to-end project ownership and sophisticated visual craft.

• Resume Optimization: Ensure your resume clearly articulates your experience with complex user types, problem-solving in ambiguous environments (0-to-1), and any experience in fintech or regulated industries. Use keywords from the job description.

• Interview Preparation: Practice articulating your design process, especially for B2B/platform products and AI-driven features. Prepare to present 2-3 strong case studies that highlight your impact and collaboration skills.

• Company Research: Deeply understand Trust & Will's mission, their B Corp status, the estate planning industry, and the specific needs of their "Professionals" segment. This will be crucial for articulating your alignment with the company's values and strategic direction.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.

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