Web Development Lead

Trupanion•Seattle, WA

4d•Hybrid

About The Position

We are a mission-driven organization focused on building high-quality, customer-facing digital experiences that scale reliably and evolve with business needs. We offer a collaborative, casual, and inclusive environment where engineers are empowered to take ownership, influence technical direction, and deliver impactful solutions. This position is open to candidates in the Seattle, WA area and follows a hybrid remote/in-office schedule, with in-office collaboration 3 days per week. We are seeking a highly hands-on Web Development Lead to guide the design, development, and operation of our public-facing and internal web platforms. This role is ideal for a senior-level technologist who combines strong people leadership through influence with deep web development expertise, and a passion for building performant, accessible, and maintainable web experiences. This is not a purely managerial role. The Web Development Lead is expected to remain deeply involved in architecture, implementation, and technical decision-making while mentoring engineers and partnering closely with product, UX, and business stakeholders.

Requirements

Sitefinity CMS, including content modeling, templates, widgets, and custom module development
ASP.NET and C# web application development
Sitefinity APIs and MVC framework
HTML5, CSS3, JavaScript, and jQuery
Modern JavaScript frameworks (e.g., React, Angular, Vue)
SQL Server, including data modeling, query development, and performance optimization
Responsive, mobile-first web development practices
Web accessibility standards, including WCAG compliance
Third-party integrations, such as payment systems, Zuora, Google reCAPTCHA, and Google Maps API
Version control using Git
Agile/Scrum tools and workflows, including JIRA
UX/UI collaboration using Figma
Azure or cloud-based hosting environments
Significant experience leading or owning web development initiatives in a production environment
Strong proficiency in modern web development technologies and CMS-driven platforms
Demonstrated ability to balance hands-on technical work with team leadership
Experience delivering customer-facing web solutions at scale
Strong communication skills, with the ability to explain technical concepts clearly
Experience working in Agile development environments

Nice To Haves

Sitefinity Cloud
Performance optimization, including caching strategies, image optimization, and page load improvements
CI/CD pipelines and modern deployment best practices
Experience leading CMS platform migrations or major site redesigns
Background working with marketing, content, or e-commerce teams
Experience with regulated or high-availability systems

Responsibilities

Serve as a hands-on technical leader, actively contributing to architecture, development, code reviews, and technical standards
Lead the design and implementation of scalable, secure, and maintainable web applications
Drive an AI-forward engineering culture, bringing demonstrated experience with AI tools such as Codex or Claude Code to improve developer efficiency and throughput
Own and evolve the overall web platform architecture, ensuring alignment with long-term business and technical goals
Provide guidance on best practices for performance, security, accessibility, and maintainability
Champion modern web development patterns and frameworks while balancing innovation with stability
Partner closely with UX/UI designers to ensure seamless translation of designs into high-quality user experiences
Ensure development work is well-scoped, well-designed, and delivered predictably
Hold the team accountable for code quality, testing, documentation, and long-term maintainability
Drive performance optimization efforts across the web stack
Support production readiness, including deployments, monitoring, and issue resolution
Lead the technical team during production incidents, including driving to root cause, resolution, and supporting after-action reports (RCA’s)
Work cross-functionally with Product, UX, Marketing, and backend engineering teams
Clearly communicate technical trade-offs, risks, and implementation impacts to both technical and non-technical stakeholders
Influence technical direction through credibility, clarity, and leadership rather than authority
Mentor and coach web developers at varying experience levels
Foster a culture of ownership, accountability, and continuous improvement
Support hiring efforts by assessing technical expertise and cultural alignment as needed