Lead Software Engineer

Trust & Will

59d • Remote

About The Position

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. This role is on the Growth squad, focused on removing friction and driving confident, fast conversion across the member journey—from first touch through initial purchase. This includes improving conversion rates, optimizing the pre-purchase experience, and validating new onboarding approaches (including conversational AI).

Requirements

• 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.

Nice To Haves

• 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.

Responsibilities

• 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.
• Design, implement, and analyze experiments (A/B tests, feature flags, etc.) to validate hypotheses and continuously improve the customer journey.
• Contribute to the development and validation of AI-powered onboarding experiences, exploring ways to guide users more effectively and increase completion and purchase confidence.
• Ensure fast, reliable, and seamless user experiences by improving application performance, reducing latency, and maintaining system stability during critical conversion flows.
• Partner closely with Product, Design, Data, and other squads to align on growth opportunities, insights, and shared outcomes across the customer journey.
• 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.
• 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.
• 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.

Benefits

• Salary + Equity
• PTO
• Flexible time off
• 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
• Access to One Medical for primary care
• Access to Cleo for family planning and caregiving
• Financial wellness benefits
• Unlimited 1:1 sessions with a UBS financial coach
• Employer-sponsored 401k with up to 4% company match
• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed