Senior Manager, Workday Systems

Trupanion, North America’s fastest-growing pet insurance provider, is seeking a Senior Manager of Workday Systems to lead the operations, governance, and continuous improvement of the Workday platform as a core pillar of our technology stack.

This role is accountable for Workday system integrity, change management, security, integrations, and upgrades across HCM, Payroll, Financial Management, Adaptive, and Performance. While the Senior Manager provides hands-on support when needed, the primary focus is on overseeing system administration, enforcing governance and compliance standards, and ensuring Workday is well-integrated with internal and external systems.

Sitting within the broader ERP team, this role ensures Workday operates reliably, securely, and in alignment with Trupanion’s technology strategy, while guiding the support team and vendor partners to deliver scalable solutions that meet evolving business needs.

This position is open to candidates in the Seattle, WA 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

• Serve as the primary Workday liaison between IT, Finance, HR, and other business units, ensuring alignment between technology solutions and business objectives.
• Lead and develop the technical Workday support team, setting priorities, and managing vendor/AMS partners.
• Oversee Workday tenant management, security, workflows, and upgrades, ensuring compliance, data integrity, and operational consistency.
• Establish and enforce governance frameworks for change management, SOX/ITGC compliance, and data integrity to meet compliance requirements.
• Drive strategies to improve system efficiency, reduce risk, and optimize recurring processes across HCM, Payroll, Finance, and Adaptive.
• Support business transformation initiatives by advising on Workday capabilities, constraints, and best practices.
• Drive alignment and integration of the Workday platform with internal and external systems—partnering with IT, Finance, HR, and other business units to ensure Workday functions as a core pillar of Trupanion’s technology stack and supports evolving business needs.
• Perform selective configuration and testing activities with a focus on designing scalable, reusable solutions and driving continuous improvement.
• Contribute to operational documentation, configuration standards, and best practices to ensure a controlled and sustainable environment.

Qualifications

• Bachelor’s level degree or equivalent work experience.
• Must have at least 6 years of relevant experience in Workday system administration, technical consulting, or business analysis, with at least 3 years in a leadership role.
• Deep expertise in Workday HCM, Payroll, Financial Management, Adaptive, and integrations (Studio, Core Connectors, EIBs, PICOFs, Web Services & REST APIs).
• Proven experience leading Workday teams and managing vendor/AMS relationships.
• Experience in Workday implementation or equivalent enterprise-level Workday experience.
• Strong background in governance, compliance frameworks, and IT controls (SOX, ITGC, security standards).

Skills

• Strategic thinker with strong business acumen and the ability to translate business requirements into technology solutions.
• Excellent leadership, team development, and people management skills.
• Strong analytical, problem-solving, and decision-making abilities.
• Exceptional oral and written communication skills, with the ability to influence at all organizational levels.
• Strong attention to detail while maintaining focus on enterprise-level priorities and outcomes.
• Ability to manage multiple initiatives simultaneously and navigate competing priorities.
• Proficiency in Microsoft Office Suite; familiarity with Agile/Scrum methodologies is a plus.
• Knowledge of Adaptive and experience with enterprise-level reporting and analytics preferred.

Compensation

• The base salary range for this position is $140,000 - 170,000 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.

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.