IT Service Desk Tech II

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.

Position Summary:

US - Seattle only: This position is open to candidates in the Seattle area. You'll work on-site at our casual, pet-friendly office five days a week.

The IT Service Desk Technician II provides advanced technical support to employees by resolving hardware, software, network, and endpoint-related issues across Windows and macOS environments. This role serves as a key escalation resource, ensuring timely issue resolution, maintaining critical IT systems and documentation, and delivering an exceptional end-user experience. The ideal candidate is a customer focused problem solver who thrives in a fast-paced environment and contributes to continuous improvement of IT services, processes, and technology initiatives.

Key Responsibilities:

• Deliver Tier II technical support for desktop, laptop, software, hardware, and network-related incidents and service requests.

• Install, configure, upgrade, and maintain end-user computing devices, operating systems, applications, and peripheral equipment.

• Accurately document incidents, resolutions, system changes, and support activities within the JIRA platform.

• Collaborate with internal IT teams to identify root causes, implement corrective actions, and enhance overall service delivery.

• Maintain high levels of employee satisfaction by providing responsive, reliable, and professional technical support.

• Perform, schedule, and monitor system alerts, work queues, back-ups, and recovery activities.

• Support mobile device management (MDM) platforms such as Intune, including device enrollment and basic configuration

• Provide support for conferencing and AV systems in meeting rooms and shared spaces

• Contribute to internal documentation and knowledge base resources

• Assist with broader IT initiatives, including system rollouts, procurement, and asset management

• Offer occasional after-hours or weekend support when needed

• Deep Windows expertise (required), including:

• OS-level troubleshooting (BSOD, event logs, performance tuning)

• BitLocker, driver/hardware issues, and power/thermal management

• 4+ years of experience in help desk, desktop support, or IT support (internship or academic lab experience considered)

• Experience supporting macOS and/or Windows in a professional environment

• Familiarity with Microsoft 365 and basic Azure Active Directory functions (e.g., user management, password resets)

• Exposure to ITSM platforms such as ServiceNow or Jira Service Management

• Understanding of MDM tools; experience with Intune is a plus

• Strong communication skills with a user-focused, service-oriented mindset

• Comfort using AI tools (e.g., CoPilot, Gemini) to improve efficiency and problem-solving

• Degree in IT, Computer Science, or related field preferred (or equivalent experience); CompTIA A+ is a plus

• Strong understanding of networking fundamentals (Wi-Fi, VPN, LAN, firewalls)

Skills:

• Advanced analytical and troubleshooting skills with the ability to identify root causes and resolve complex technical issues efficiently

• Experience working in global, distributed, or multicultural organizations and supporting a diverse employee population

• Proven ability to identify process improvement opportunities and contribute to service desk optimization initiatives

• Strong technical documentation and knowledge management skills, including creating clear procedures and support articles

• Excellent organizational and time-management skills with the ability to manage competing priorities in a fast-paced environment

• Strong written and verbal communication skills with the ability to build positive relationships across technical and non-technical teams.

Compensation:

• The base hourly range for this position is $33.65 - $35.33 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.

Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment visa at this time.