Web Development Lead

Web Development Lead Company Description Trupanion is a leading provider of medical insurance for cats and dogs in North America. Our mission is to help loving, responsible pet owners budget and care for their pets. At Trupanion, we offer a collaborative, casual, and pet-friendly environment where everyone is encouraged to be themselves.

Job Description

• Overview 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. Key Responsibilities Hands-On Technical Leadership
• 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 Delivery, Quality & Operations
• 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) Collaboration & Stakeholder Engagement
• 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 Team Leadership & Mentorship
• 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 Technical Skills & Expertise
• 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
• Sitefinity Cloud (preferred/bonus)
• Performance optimization, including caching strategies, image optimization, and page load improvements
• CI/CD pipelines and modern deployment best practices Qualifications Required
• 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 Preferred / Nice to Have
• 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

Affirma is an Equal Opportunity Employer and does not make employment decisions or otherwise discriminates based on race, creed, color, national origin, sex, military status, sexual orientation, or the presence of any sensory, mental, or physical disability, genetic information, or any other category protected by law.