Lead Software Engineer

Core Responsibilities

• Conversion & Funnel Optimization: Own and improve the end-to-end pre-purchase experience (Home → Registration → Cart → Purchase), identifying and eliminating friction points to increase conversion rates and revenue.
• Experimentation & Rapid Iteration: Design, implement, and analyze experiments (A/B tests, feature flags, etc.) to validate hypotheses and continuously improve the customer journey.
• AI-Driven Onboarding: Contribute to the development and validation of AI-powered onboarding experiences, exploring ways to guide users more effectively and increase completion and purchase confidence.
• Performance & Reliability: Ensure fast, reliable, and seamless user experiences by improving application performance, reducing latency, and maintaining system stability during critical conversion flows.
• Cross-Functional Collaboration: Partner closely with Product, Design, Data, and other squads to align on growth opportunities, insights, and shared outcomes across the customer journey.

Technical Leadership & Impact

• Design and deliver scalable, high-performing frontend and backend systems that directly impact conversion and user experience.
• Drive a data-informed engineering culture, using metrics, experimentation results, and user behavior insights to guide technical decisions.
• Leverage AI strategically—not just as a tool, but as a core component of the product experience—to improve onboarding, personalization, and developer efficiency.
• Champion best practices in testing, observability, and CI/CD to enable safe, fast iteration within high-impact areas of the funnel.
• Continuously identify and address bottlenecks in the user journey, balancing speed of delivery with long-term system health.

Quality & Impact

• Build high-quality, production-ready features that are optimized for performance, reliability, and measurable business impact.
• Prioritize improvements that directly reduce drop-off, increase purchase confidence, and enhance the overall member experience.
• Use monitoring, analytics, and user feedback to proactively identify issues and opportunities within the conversion funnel.
• Continuously reduce technical debt in high-traffic, high-impact areas to enable faster experimentation and iteration.

Collaboration, Innovation & Mentorship

• Work closely with cross-functional partners to align on growth strategies, ensuring engineering efforts are tightly coupled to business and user outcomes.
• Develop a strong understanding of customer behavior, funnel metrics, and experimentation frameworks to inform decision-making.
• Mentor engineers in building with a growth mindset—focusing on impact, iteration speed, and measurable outcomes.
• Communicate clearly across technical and non-technical stakeholders, especially around experiments, trade-offs, and results.
• Foster a culture of experimentation, learning, and continuous improvement, where ideas are tested quickly and insights are shared openly.

Qualifications:

• 7+ years of professional software engineering experience, ideally in high-performing, product-driven teams with a focus on user experience and measurable outcomes.
• Strong proficiency in building modern frontend applications (React, TypeScript), with a deep understanding of performance, usability, and conversion-focused design.
• Experience designing and working with APIs and data models (e.g., MongoDB, Postgres), with an emphasis on supporting fast, reliable user flows and experimentation.
• Hands-on experience building and operating applications in AWS, using infrastructure-as-code tools (e.g., CloudFormation, AWS CDK).
• Proven ability to write clean, maintainable, and well-tested code, with a focus on enabling rapid iteration through strong testing practices and CI/CD pipelines.
• Experience working in experimentation-driven environments, including A/B testing, feature flags, and using data to inform product and engineering decisions.
• Strong debugging and performance optimization skills, with the ability to identify and resolve bottlenecks in critical user journeys.
• Familiarity with observability tools and practices (logging, monitoring, tracing) to ensure reliability in high-impact areas of the funnel.
• Experience leveraging AI-assisted development tools (e.g., GitHub Copilot, Cursor) to improve velocity, and interest in applying AI to enhance user onboarding and product experiences.
• Ability to define, track, and act on meaningful product and engineering metrics (e.g., conversion rates, drop-off points, latency) to drive continuous improvement.
• Understanding of security and privacy best practices, especially as they relate to handling sensitive user data in customer-facing flows.
• 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)

Bonus Points for:

• Experience working in a tech company or high-growth startup.
• Willingness to contribute outside of core expertise to drive impactful work forward.
• Developing infrastructure as code in Go.
• 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 techniques.
• Active contributions to open-source projects or participation in developer communities.

Employee Benefits & Perks

• Compensation: Salary + Equity

  • Our salary range for this position is $166k - $215k, 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). To exercise these rights, contact legal@trustandwill.com. For more information, visit ourprivacy policy.

Trust & Will may use AI tools to assist with administrative recruiting tasks. All final hiring decisions are made by people. For accommodations, contact people-ops@trustandwill.com.

This position will remain open until filled, but applications received by April 30, 2026 will receive priority consideration.