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. 

Trupanion is seeking a strategic, execution‑oriented Director of Infrastructure, Cloud & DevOps to lead the next phase of our cloud‑first transformation while maintaining strong ownership of our hybrid infrastructure environment. This leader will evolve our Azure‑based platform into a highly automated, scalable, and developer‑centric ecosystem, while ensuring reliability, security, and performance across both cloud and on‑premise infrastructure. 

This role partners closely with the VP of Technology Operations, CIO and Engineering leadership. Operating at the intersection of Engineering and Technology Operations, this leader will build and scale a high‑impact DevOps and Platform Engineering capability while driving operational excellence across core infrastructure—including data centers, servers, networking, security, and resiliency. The role establishes automation, standardization, and self‑service as core principles across both infrastructure and application delivery. 

This position is accountable for how Trupanion builds, deploys, and operates technology in a highly available, real‑time, and regulated environment supporting critical pet health and claims systems. It ensures the stability and compliance of foundational infrastructure while accelerating modernization through DevOps practices, directly influencing speed‑to‑market, platform resilience, and the reliability of the member experience. 

This position is open to candidates in the Seattle area. You will have a hybrid remote/in-office schedule where you will work from our casual, pet-friendly office at least 3 days a week. 

Responsibilities:

• Define and execute the enterprise Cloud, Infrastructure, and Platform Engineering strategy 
• Lead and develop a world-class Infrastructure, Cloud, DevOps, and SRE organization
• Accelerate cloud transformation through Azure, Kubernetes, automation, and modern engineering practices
• Establish Infrastructure as Code, CI/CD, and self-service platforms as foundational capabilities. 
• Deliver highly available, scalable, secure, and resilient hybrid infrastructure services
• Drive reliability engineering, observability, incident response, and operational excellence programs
• Modernize legacy platforms and enable cloud-native architectures across the enterprise
• Embed security, compliance, governance, and risk management into platform operations
• Strengthen disaster recovery, business continuity, and enterprise resiliency capabilities
• Optimize technology investments through FinOps, vendor management, and capacity planning 
• Partner with Engineering and Product leaders to improve developer experience and delivery velocity
• Influence executive technology strategy through metrics, insights, and transformation leadership 

Qualifications:

• 10+ years of progressive leadership experience across Infrastructure, Cloud, DevOps, Platform Engineering, or Site Reliability Engineering functions
• Proven experience leading enterprise cloud transformation, infrastructure modernization, and operational excellence initiatives within complex, highly available environments
• Strong Azure experience preferred; equivalent AWS or GCP leadership experience with demonstrated ability to operationalize cloud platforms at scale
• Experience building and leading high-performing technical organizations, including infrastructure, cloud, DevOps, platform engineering, or SRE teams
• Demonstrated success partnering with executive leadership to define technology strategy, investment priorities, and transformation roadmaps
• Bachelor's degree in Information Technology, Computer Science, Engineering, or equivalent experience

Skills: 

• Proven success building and scaling Infrastructure, Cloud, DevOps, Platform Engineering, or SRE organizations
• Strong leadership experience managing enterprise infrastructure environments, including cloud platforms, data centers, compute, storage, networking, and identity services
• Deep understanding of enterprise networking, including SD-WAN, routing, switching, firewalls, and hybrid connectivity architectures
• Expertise with Azure services, Kubernetes (AKS preferred), containerization, and cloud-native architecture patterns
• Strong experience implementing Infrastructure as Code (IaC), automation frameworks, CI/CD pipelines, and platform engineering capabilities
• Experience establishing observability, reliability engineering, incident management, and service resiliency programs
• Proven experience leading disaster recovery, business continuity, high availability, and enterprise resiliency strategies
• Strong understanding of cloud governance, security controls, compliance frameworks, identity management, and risk management practices
• Experience driving patch management, vulnerability remediation, infrastructure lifecycle management, and operational governance at scale
• Demonstrated success managing SOX controls, audit readiness, User Access Reviews (UAR), and regulated technology environments
• Experience with cloud cost optimization, FinOps practices, vendor management, budgeting, and capacity planning
• Excellent executive communication, stakeholder management, and cross-functional leadership skills

Compensation:

• The base pay range for this position is $150,000 -$180,000, 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.

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.