Web Development Lead

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.

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
• 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

• 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

Additional Information

Compensation:

• The base salary range for this position is $150,000 -$160,000 on a full-time schedule.
• Along with base compensation, Trupanion employees are currently eligible for monthly bonuses.
• We want all employees to be invested in Trupanion’s success, so we grant Restricted Stock Units to all new team members. Our new hire grants vest over 4 years.

Benefits and Perks:

• Full medical, dental, and vision benefits at no cost to the employee
• Four weeks of paid time off and 9 paid float holidays (you can decide which days are most important to you!)
• Five-week sabbatical after five years of employment
• Open, casual, pet-friendly, and fun office environment
• Free medical health insurance for your pet (1 dog or cat)
• Paid time off to volunteer at nonprofit organizations
• Seattle Office Amenities: Free on-site gym, free dog walking services for office pets during business hours, free parking, and paid ORCA cards.

For more information about Trupanion, visit https://trupanion.com/about

Learn more about how Trupanion has revolutionized our industry and the reimbursement model: https://www.youtube.com/watch?v=vdWZ4KHiPTQ

Trupanion is an equal-opportunity employer and embraces diversity. We are committed to building a team that represents a variety of backgrounds, abilities, perspectives, and skills.