Trust and Will

Title: Senior Product Designer II, Professionals Location: United States Job Description: 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. If you would like to join us, we are looking for a Senior Product Designer II that will shape how financial advisors, attorneys, and nonprofit partners help millions of families get their estate plans in place. You'll be embedded in our Professionals squad - the fastest-growing part of our business - owning complex, multi-sided design problems end-to-end from research through ship. About You: - You've designed complex B2B or platform products and understand that professionals don't have time for a product that gets in their way, and who need to trust what they're putting in front of their clients. - Not everything will be defined when it lands on your plate. You're comfortable with that - you know how to find your footing and move forward without waiting for someone to hand you a cleaner brief. - You have strong opinions about visual design - hierarchy, type, color, motion, and the fluency to act on them. You think about how a product functions as well as how it feels, and your work reflects that. - You understand that influence is part of the job. You can build a design rationale that lands with a skeptical PM, articulate tradeoffs to an engineer under deadline, and make a case for the right call in a room that's leaning the other way. You push back when it matters and let go when it doesn't. - You're genuinely excited about what AI can do for both your design process and the products you build. - Most importantly: you care about what we're building here. Estate planning isn't an abstract product category. It's the difference between a family that's protected and one that isn't and that motivates you. About the Role: Most families don't have an estate plan. And the ones who do often got there because a financial advisor, attorney, or nonprofit partner guided them there. That's the platform you'll be designing for. Our Professionals channel serves more than 15,000 wealth planning professionals who help millions of families get their plans in place. It's the fastest-growing part of our business — and one of the most consequential. The work you do here shapes how advisors show up for their clients at some of the most important moments of their lives. This is a high-autonomy role. You'll be embedded in the Professionals squad, working alongside Product and Engineering from discovery through delivery. You'll also bring your thinking to the broader product when the team needs it. What You’ll Do: - Start with the right problem. Before a single screen gets designed, you'll do the work of understanding what actually needs solving. That means getting into the research - interviews, behavioral data, what the market is doing - and turning it into a point of view that the team can actually build toward. Good synthesis is a design skill. You have it. - Shape what gets prioritized. You'll work closely with PMs to influence the roadmap. When you have a clear read on what users need and why it matters, you'll bring that in before decisions get locked in. - Own complex, multi-sided design problems end-to-end. The Professionals platform serves both the advisors using our tools and the clients they're planning for. You'll hold both perspectives simultaneously and design for the tension between them — building trust, clarity, and confidence into every touchpoint. - Set the craft bar. You'll bring a sophisticated visual design sensibility to a product that has historically leaned functional. That means strong hierarchy, considered interaction patterns, and an aesthetic that earns trust of professionals who spend their days in financial tools. - Move fast and know when to slow down. Startup pace is real here. You'll make smart tradeoffs - balancing scope, effort, and opportunity cost with Product and Engineering. - Use AI as a design tool and a design medium. You'll integrate AI tools into your workflow for research synthesis, concept generation, and rapid prototyping. You'll design AI-powered features with care, understanding what the technology does well, where it falls short, and how to introduce it in ways that feel trustworthy and helpful. - Contribute to systems. You'll help extend our design system in ways that scale - building reusable patterns that hold up across the Professionals platform and beyond. - Raise the bar for the team around you. You'll bring a point of view on where design is headed - sharing thinking, sparking conversations, and helping the team stay sharp on craft, process, and what's possible. You show up fully in critique and bring an energy that elevates the whole group. Qualifications: - 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 — this space carries real stakes for real families and you take that seriously - This position is available to candidates residing in the following states only: California (CA), Colorado (CO), Florida (FL), Georgia (GA), Idaho (ID), Illinois (IL), Maryland (MD), New Jersey (NJ), New York (NY), North Carolina (NC), Pennsylvania (PA), Texas (TX), Vermont (VT), Nevada (NV), Utah (UT) Employee Benefits & Perks: - Compensation: Salary + Equity - Our salary range for this position is $175k - $200k, 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 day - Paid time off to volunteer in your community - Health and Wellness Benefits - Exceptional health benefits including medical, dental, vision, life, and disability insurance - we cover 100% of premiums for employees and dependents on medical coverage - 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. We support the complexity of a remote world with the needs of families - 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 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. California Privacy Notice: Trust & Will collects personal information from applicants including identifiers, professional/employment history, and education information 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 (subject to exceptions).

Title: Senior Product & Growth Analyst Location: CA, CO, FL, GA, ID, IL, MD, NJ, NY, NC, SC, PA, TX, VT, United States Job Description: 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. If you are passionate about contributing to a high-impact mission and want to work in a collaborative environment where your skills and expertise will be valued, we would love to hear from you! About You - You are a clear, concise communicator who can translate a complex regression or other mathematical reasoning into a one-paragraph recommendation for a non-technical stakeholder. - You are a data scientist and analyst hybrid equally comfortable building a causal inference model and presenting the business implication to a VP. - You have startup experience and know what it means to stand up an analytics function, ship scrappy analyses, and build toward rigor not wait for it. - You treat experimentation as a discipline, not a buzzword. You design tests, size samples, interpret results correctly, and know when an A/B test isn't the right tool. - You think in systems and funnels you connect product behavior to business outcomes and are never satisfied stopping at the metric without asking why. - You operate with high autonomy and you identify the most important question, define the approach, execute the analysis, and deliver the recommendation without a detailed playbook. - You are AI-curious and actively explore how AI tools can accelerate your analytical workflows, automate repetitive queries, and surface insights faster. - This position is available to candidates residing in the following states only: California (CA), Colorado (CO), Florida (FL), Georgia (GA), Idaho (ID), Illinois (IL), Maryland (MD), New Jersey (NJ), New York (NY), North Carolina (NC), South Carolina (SC), Pennsylvania (PA), Texas (TX), Vermont (VT) About the Role We're looking for a Senior Product & Growth Analyst to own the analytical engine behind Trust & Will's growth. This is a high-ownership role: you'll work across product, marketing, and revenue to understand what's driving conversion, retention, and lifetime value and you'll translate those findings into decisions that move the business. This is not a reporting role. You will define the questions worth asking, build the models that answer them, run experiments to test the hypotheses, and guide the roadmap based on what the data shows. You'll partner closely with the Director of Data Engineering, product managers, and growth leadership and you'll have direct access to senior stakeholders. The core challenge is analytically interesting: estate planning is a low-frequency, high-intent product with a B2C direct channel and a growing B2B2C advisor network. Understanding how different user segments activate, convert, and retain and which levers compound requires real analytical depth. You'll have the data, the infrastructure, and the mandate to figure it out. Product Analytics - Instrument and analyze user behavior across the Trust & Will product activation milestones, feature adoption, onboarding drop-off, and engagement patterns using PostHog/Other. - Develop and maintain the core product analytics dashboard and data models, enabling self-serve access for PMs, designers, and marketers. - Identify friction points in the estate plan creation flow and quantify the impact of proposed product changes before and after release. Growth & Funnel Analytics - Own end-to-end funnel analysis from acquisition through plan completion and membership renewal identifying drop-off points, segmenting by channel and user type, and prioritizing optimization opportunities by expected impact. - Build and maintain cohort models to track retention and engagement across consumer and advisor-sourced customers; surface early-warning signals for churn. - For example, develop and maintain LTV models that account for plan type, channel, upsell pathways, and membership behavior directly informing marketing budget allocation and partnership ROI decisions. - Design and execute multi-touch attribution analysis across paid media, organic, AARP partnership, and advisor referral channels. Experimentation - Lead the experimentation program end-to-end: hypothesis formation, experimental design, sample size and power analysis, execution in PostHog/Others, statistical analysis, and business recommendation. - Build guardrails and standards for when and how to run experiments including when to apply experimental methods propensity score matching and when randomized testing isn't feasible. - Partner with product and marketing teams to prioritize the test backlog based on expected impact and feasibility. Data Science & Modeling - Build predictive models for churn risk, conversion propensity, and upsell likelihood using early behavioral signals. - Develop user segmentation frameworks that inform personalization, messaging, and product prioritization. - Apply statistical rigor to all analytical work communicating uncertainty, flagging limitations, and recommending confidence thresholds before decisions are made. Stakeholder Partnership & Communication - Serve as the primary analytics partner for product and growth leadership, owning the analytical workstreams that support quarterly roadmap decisions. - Prepare and deliver data-driven recommendations to senior stakeholders and the executive team punchline first, minimum viable backstory, clear ask. - Mentor junior analysts and product/eng on methodology, communication, and prioritization; help build team-wide analytical standards. Qualifications Core Experience - 8-12+ years of experience in analytics, data science, or a closely related quantitative role. - Prior experience in a high-growth startup environment you've operated with limited resources, ambiguous data, and shifting priorities and delivered anyway. - Demonstrated data science background: you've built predictive models, designed and analyzed experiments, and applied statistical methods to business problems in production settings. - Experience owning an analytics domain end-to-end not just answering requests, but generating the questions and driving decisions. Technical Skills - SQL: Advanced window functions, CTEs, complex joins, query optimization on large datasets. - Python: Proficient pandas, statsmodels, scikit-learn, matplotlib/seaborn; you write clean, reproducible analytical code. - Experimentation: End-to-end A/B test ownership, power analysis, and working knowledge of experimental methods. Product Analytics: PostHog, Amplitude, Mixpanel, or equivalent funnel analysis, cohort analysis, event instrumentation. - BI / Visualization:ThoughtSpot, Omni, or equivalent building dashboards that enable self-serve, not just answering one-off requests. - Data Modeling: Familiarity with dbt and the analytical data modeling - like ActivitySchema, Star Schema etc… Bonus Points - Experience in fintech, legaltech, insurtech, or another regulated consumer vertical. - Familiarity with Bayesian methods or causal inference frameworks beyond standard A/B testing. - Experience with product-led growth (PLG) motions or B2B2C business models. - Background in subscription, membership, or low-frequency/high-intent consumer products. - Contributions to building an analytics function from scratch metrics frameworks, data dictionaries, experimentation standards. - Comfort working with an AI Data Analyst tool in a self-serve analytics context. Employee Benefits & Perks - Compensation: Salary + Equity - Our salary range for this position is $140,000 - $190,000, 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 day - Paid time off to volunteer in your community - Health and Wellness Benefits - Exceptional health benefits including medical, dental, vision, life, and disability insurance - we cover 100% of premiums for employees and dependents on medical coverage - 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. We support the complexity of a remote world with the needs of families - 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 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. California Privacy Notice: Trust & Will collects personal information from applicants including identifiers, professional/employment history, and education information 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 (subject to exceptions).

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: You are a technical leader, proficient in TypeScript, React, Next.js , and Node.js , with a strong foundation in system design and cloud-native development. You have a problem-solving mindset, tackling system-wide challenges with strategic thinking and a focus on high-impact solutions. You see AI not as a tool but as a fundamental shift in engineering, and you actively seek opportunities to harness its potential. You thrive in fast-moving, high-performance environments, navigating ambiguity, aligning stakeholders, and delivering results. You are a mentor and collaborator, fostering team growth through thoughtful guidance, clear communication, and constructive feedback. You are passionate about writing maintainable, testable code, ensuring software quality through modern DevOps and observability best practices. About the Role: Technical Leadership, Quality & Impact Architect, design, and deliver large-scale, high-performance features across the stack. Drive system-level design and data modeling, ensuring scalable, reliable, and maintainable solutions aligned with organizational best practices. Think expansively about AI—how to build with it, integrate it into features, and leverage it to drive innovation Own technical projects end-to-end, ensuring efficient delivery, optimal performance, extensibility, and reliability. Lead and contribute operational engineering strategies, including test automation observability and modern CI/CD practices. Collaborate on cloud architecture decisions to deliver resilient, cost-effective, and secure solutions. Deliver high-quality, production-ready code that adheres to coding and operational best practices, accounts for edge cases, and is self-documenting for maintainability. Lead efforts to reduce technical debt and optimize system performance through continuous refactoring and advanced debugging practices. Drive improvements in system reliability, scalability, and performance, leveraging monitoring and observability tools to proactively identify bottlenecks and issues. Champion a culture of learning by facilitating design discussions, providing constructive feedback, and fostering collaboration across teams. Collaboration, Innovation & Mentorship Partner with product managers, designers, and cross-functional stakeholders to align technical efforts with business objectives and customer needs. Mentor engineers across skill levels, providing guidance in software patterns, architecture, DevOps, and problem-solving techniques to foster technical growth. Communicate complex technical topics clearly to both technical and non-technical audiences, ensuring alignment and shared understanding across teams. Promote knowledge sharing through technical documentation, share-outs, and peer collaboration to elevate team capabilities. Actively explore how AI can improve developer efficiency, automate workflows, and enhance system reliability. Explore and advocate for cutting-edge tools and technologies, incorporating them into the engineering stack when appropriate to advance capabilities. Lead initiatives to drive innovation and continuously improve engineering processes, challenging the status quo to deliver greater value. Contribute to system-wide architectural discussions to ensure alignment with strategic goals and future scalability. Qualifications: 5+ years of professional full-stack development experience in high-performing teams. Demonstrated proficiency in TypeScript, React, Next.js, and Node.js . Advanced skills in system design, data modeling (MongoDB, Postgres) , and cloud-native development (AWS) . Skilled in test-driven development, CI/CD pipelines, and modern DevOps best practices. Proficient in debugging complex systems and implementing observability practices to ensure operational excellence. Demonstrated ability in integrating AI code assistants to enhance development productivity and code quality, with hands-on experience using at least one of the following: GitHub Copilot , Cursor , RooCode , or RooCline . Proven ability to mentor engineers, align technical solutions with business goals, and influence cross-functional teams. Strong analytical skills, with a passion for identifying and prioritizing high-impact solutions across engineering challenges. This position is available to candidates residing in the following states only: California (CA), Colorado (CO), Florida (FL), Georgia (GA), Idaho (ID), Illinois (IL), Maryland (MD), New Jersey (NJ), New York (NY), North Carolina (NC), Pennsylvania (PA), Texas (TX), Vermont (VT) Bonus Points for: Experience in tech companies or high-growth startups. Familiarity with Agile development methodologies (Scrum/Kanban, JIRA). Hands-on experience with Docker , Kubernetes , or other container orchestration tools. Experience with pair programming and collaborative development. Experience integrating AI-assisted workflows effectively into complex software engineering tasks. Contributions to open-source projects or active participation in developer communities. Employee Benefits & Perks: Compensation: Salary + Equity Our salary range for this position is $140,000 - $175,000, 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 day 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, financial coach support, and employer-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. California Privacy Notice: Trust & Will collects personal information from applicants including identifiers, professional/employment history, and education information 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 (subject to exceptions). To exercise these rights, contact legal@trustandwill.com. For more information, visit our privacy policy.