Trupanion

Medical Insurance

WebDevelopmentLead

$150–160k Seattle, Washington, United States FULL TIME Remote Friendly
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for mid candidates.

The Brief

“Web Development Lead at Trupanion. Skills: Web Development, Sitefinity CMS, ASP. NET, C#. Serve as hands-on technical leader. Contribute to architecture, development, code reviews”

What You'll Achieve.

Building performant, accessible, maintainable web experiences; Ensuring alignment with long-term business and technical goals; Seamless translation of designs into high-quality user experiences; Improve developer efficiency and throughput

Industry & Context.

Medical Insurance
Problems you'll solve

Technical decision-making; Issue resolution; Driving to root cause

What They're Looking For.

Must Have

Significant experience leading or owning web development initiatives in a production environment, 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, Communication skills, with the ability to explain technical concepts clearly, Experience working in Agile development environments

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, Sitefinity Cloud

What You'll Do.

Serve as hands-on technical leader

Contribute to architecture

Lead design and implementation

Drive AI-forward engineering culture

Own and evolve web platform architecture

Provide guidance on best practices

Champion modern web development patterns

Ensure development work is well-scoped

Hold team accountable for code quality

Drive performance optimization efforts

Support production readiness

Lead technical team during incidents

Mentor and coach web developers

Foster culture of ownership

Support hiring efforts

How You'll Work.

Team & Collaboration

Partner closely with UX/UI designers; Work cross-functionally with Product, UX, Marketing, backend engineering; Clearly communicate technical trade-offs; Influence technical direction through credibility

Communication Scope

Clearly communicate technical trade-offs, risks, and implementation impacts; Explain technical concepts clearly

Process & Methodology

Ensure development work is delivered predictably, Lead technical team during production incidents

Full Job 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. This position is open to candidates in theSeattle, WA area and follows a hybrid remote/in-office schedule, with in-office collaboration 3 days per week. 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 & Operatio

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