Staff Product Engineer

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.

As a Staff Product Engineer, you take product work from a customer or business need through production, across both product and engineering. You combine product judgment, full-stack engineering and agent-driven development, partner closely with product management, design and engineering, and carry a project independently when the work calls for it. This is a staff-level individual contributor role with company-wide scope.

About the Role:

• Own product and engineering work from intake through launch, and stay with it after it ships.
• Partner with product managers on the problem, the customer and the business case, and bring a view on scope, sequencing and what not to build.
• Partner with engineering leaders and senior engineers on architecture, design reviews and technical direction.
• Talk directly with members, advisors, attorneys and internal teams to understand use cases.
• Design and ship across the platform (UI, services, data and integrations).
• Carry a project end to end, partnering with others when the work calls for it.
• Build testing, safe release, and production visibility into the work, and make tradeoffs explicit.
• Move across product areas as priorities change, pairing with others, and leaving behind systems the team can reuse.

Qualifications:

• 8+ years building and shipping customer-facing software, or equivalent depth, including work at a staff, principal or lead level.
• Staff-level product judgment: framing an ambiguous problem, defining success, setting scope and deciding what not to build.
• Staff-level engineering depth: system design across user interfaces, APIs and relational data, with sound tradeoffs between speed, reliability and long-term maintainability.
• A record of shipping from idea to production, with or without a detailed spec, and owning the result after launch.
• Experience partnering as a peer with product managers, designers and engineering leaders, and bringing decisions through design and architecture review.
• Comfort working directly with customers and non-technical partners, and turning what they say into a scope.
• Care for quality, security, and reliability in production, especially in products that handle sensitive personal and financial information.
• Influence without formal authority, through clear writing, clear tradeoffs, pairing and example.
• 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), Tennessee (TN), Texas (TX), Vermont (VT), Nevada (NV), Utah (UT)

How We Work: AI-First

• Works mainly by specifying outcomes: a clear goal, constraints and acceptance criteria that agents (Claude Code, Cursor, Codex or similar) pursue without continuous supervision.
• Builds validation into the system, through tests, evaluations, automated checks and production signals, so agents confirm their own work before a person reviews the result.
• Sets and governs the boundaries agents work within, including what they may change, release or access, with extra care around customer data, security and production.
• Handles the exceptions agents escalate, and keeps step-by-step supervision for work where the risk calls for it.
• Helps other engineers move from using AI as an assistant toward delegating whole outcomes, safely.
• Candidates must walk through a real outcome they delegated to agents during the interview, including how it was validated and where a person stepped in.

Bonus Points for:

• Experience in regulated or high-trust products, such as financial services, legal, insurance or health.
• Founder, founding engineer or early product engineer experience building a product from scratch.
• Experience writing product specs, running customer research or working in product management.
• Experience leading cross-team work that left a team with a better way to build.
• Experience working on high-autonomy, remote-first teams where problems arrive loosely defined.

What Success Looks Like:

• Important product work ships, and the members, advisors or teams who needed it use it.
• Product managers and engineering leaders see this role as a partner who makes their plans easier to deliver.
• Architecture and design decisions are reviewed, written down and fit the platform.
• What ships can be tested, watched and reversed.
• Engineers and product partners who work with this person ship faster at the same, or higher, quality bar.
• Agents deliver and validate defined outcomes within clear boundaries, and people handle the exceptions.

Full-time Employee Benefits & Perks:

• Compensation: Salary + Equity
  • Our salary range for this position is $225,000 - $250,000, 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.
  • 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). To exercise these rights, contact View email address on aiapply.co. For more information, visit our privacy policy.

Trust & Will may use AI tools to assist with administrative recruiting tasks. All final hiring decisions are made by people. For accommodations, contact View email address on aiapply.co.

Applications will be accepted through 10/26/26. If the deadline is extended, this posting will be updated.