Lead Software Engineer

Trust & Will is the leading digital estate planning platform, trusted by over one million users. The role involves leading technical initiatives to enhance the user experience and optimize the pre-purchase journey, focusing on conversion rates and leveraging AI-driven solutions.

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

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
• 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