Web Development Lead

• Compensation: USD 150,000 - USD 160,000 - yearly

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
.*

Overview

We areseekinga 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 strongpeopleleadership through influence with deep web developmentexpertise,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 implementationimpactsto 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 technicalexpertiseand cultural alignmentas 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
• 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
• Azure or cloud-based hosting environments
• Sitefinity Cloud
  (preferred/bonus)
• Performance optimization
  , including caching strategies, image optimization, and page load improvements

Required

• Significant experience leading or owning web development initiatives in a production environment
• Strongproficiencyin 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:

• Thebasesalaryrange for this position is$-$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’ssuccess, 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…