Web Development Lead

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.

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. 

*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.*

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 

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 

Compensation:  

• The base salary range for this position is $150,000,000 -$160,000, on a full-time schedule.  
• Along with base salary, Trupanion employees may be 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.

We will ensure that individuals are provided reasonable accommodation to participate in the job application or interview process, perform essential job functions, and receive other benefits and privileges of employment. Please contact us to request accommodations.