Senior Manager, Workday Systems

Trupanion•Seattle, WA

3d•Hybrid

About The Position

Trupanion is seeking a Senior Manager of Workday Systems to lead the operations, governance, and continuous improvement of Workday as a core part of its technology stack. The role is accountable for system integrity, change management, security, integrations, and upgrades across HCM, Payroll, Financial Management, Adaptive, and Performance. While hands-on support may be needed, the primary focus is overseeing system administration, governance and compliance, and integrations with internal and external systems. The position sits within the ERP team and ensures Workday operates reliably, securely, and in alignment with Trupanion’s technology strategy while guiding support staff and vendor partners toward scalable solutions. The role serves as the primary Workday liaison across IT, Finance, HR, and other business units; leads the technical support team; oversees tenant management, security, workflows, and upgrades; and establishes governance for change management, SOX/ITGC compliance, and data integrity. It also supports business transformation, improves system efficiency and recurring processes, and contributes configuration, testing, documentation, and standards for a controlled, sustainable Workday environment. The position is open to candidates in the Seattle, Washington area and follows a hybrid remote/in-office schedule, with at least three days each week in Trupanion’s casual, pet-friendly office.

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.
At least 3 years of experience 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.
Strategic thinking, business acumen, and ability to translate business requirements into technology solutions.
Strong leadership, team development, and people management skills.
Strong analytical, problem-solving, and decision-making abilities.
Excellent oral and written communication skills, including 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 and navigate competing priorities.
Proficiency in Microsoft Office Suite.

Nice To Haves

Familiarity with Agile/Scrum methodologies.
Knowledge of Adaptive.
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.
Develop strategies to improve system efficiency, reduce risk, and optimize recurring processes across HCM, Payroll, Finance, and Adaptive.
Advise on Workday capabilities, constraints, and best practices in support of business transformation initiatives.
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, emphasizing 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.
Nine paid float holidays.
Five-week sabbatical after five years of employment.
Monthly bonuses; employees are currently eligible.
Restricted Stock Units granted to all new team members, vesting over four years.
Free medical health insurance for one dog or cat.
Paid time off to volunteer at nonprofit organizations.
Free on-site gym.
Free dog-walking services for office pets during business hours.
Free parking.
Paid ORCA cards.