Senior Manager, Workday Systems

Trupanion • Seattle, WA

4d • $140,000 - $170,000 • Hybrid

About The Position

Trupanion is seeking a Senior Manager of Workday Systems to lead the operations, governance, and continuous improvement of the Workday platform as a core part of its technology stack. This role is accountable for system integrity, change management, security, integrations, and upgrades across HCM, Payroll, Financial Management, Adaptive, and Performance. While the position provides hands-on support when needed, its primary focus is overseeing system administration, enforcing governance and compliance standards, and ensuring Workday is well-integrated with internal and external systems.

Part of the broader ERP team, the Senior Manager ensures Workday operates reliably and securely in alignment with Trupanion’s technology strategy. The role guides the support team and vendor partners in delivering scalable solutions for evolving business needs. Candidates must be in the Seattle, Washington area and work a hybrid schedule in the company’s office at least three days per week.

Requirements

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

Nice To Haves

• Familiarity with Agile/Scrum methodologies.
• Knowledge of Adaptive and experience with enterprise-level reporting and analytics.

Responsibilities

• Serve as the primary Workday liaison between IT, Finance, HR, and other business units, aligning technology solutions with business objectives.
• Lead and develop the technical Workday support team, set priorities, and manage vendor and AMS partners.
• Oversee Workday tenant management, security, workflows, and upgrades to ensure compliance, data integrity, and operational consistency.
• Establish and enforce governance frameworks for change management, SOX/ITGC compliance, and data integrity.
• 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 Workday with internal and external systems in partnership with IT, Finance, HR, and other business units.
• Perform selective configuration and testing, focusing on scalable, reusable solutions and continuous improvement.
• Contribute to operational documentation, configuration standards, and best practices for a controlled and sustainable environment.

Benefits

• Full medical, dental, and vision benefits at no cost to the employee.
• Four weeks of paid time off and nine paid float holidays.
• Five-week sabbatical after five years of employment.
• Casual, pet-friendly office environment.
• Free medical health insurance for one dog or cat.
• Paid time off to volunteer at nonprofit organizations.
• Seattle office amenities include a free on-site gym, free dog walking services for office pets during business hours, free parking, and paid ORCA cards.
• Employees are currently eligible for monthly bonuses.
• Restricted Stock Unit grants for all new team members, vesting over four years.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior