Principal Workday Architect, Benefits & Absence

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.

Our People and Places team's ambition is that our People Experience is a key differentiator and reason for candidates to choose Toast and employees to stay at Toast, as much as our Products are today. Our People Products team goal is to amplify the People Team’s ambition by developing AI-powered conversational self-service products to deliver personalized employee experiences and insights in the flow of work through cloud based scalable, integrated, compliant products to unleash productivity and boost engagement of Toasters and possibly also ship to Toast customers.

We are seeking a strategic and product-minded Principal Workday Architect to join our People Products team. In this role, you will report to the Sr. Manager of People Products, and drive the vision, design, and delivery of Workday solutions that power our employee experience and operational excellence. You'll work closely with People, Total Rewards, Finance, and IT stakeholders to align Workday configurations and integrations with business goals, ensuring solutions are scalable and successfully adopted.

A Day in the Life (Responsibilities)

System Configuration & Process Optimization

• Architect Global Benefits and Absence Plans: Own the strategic design and configuration of all absence and benefit plans, plan types, coverage levels, and complex eligibility rules, ensuring alignment with global and regional philosophies
• Lead Enrollment Events: Configure and manage end-to-end Open Enrollment and Life Events/Change Benefits Events, defining workflow rules, validation processes, and the employee self-service experience
• Own Carrier Integrations: Serve as the technical owner for the Workday Cloud Connect for Benefits, architecting and validating the secure and accurate transmission of enrollment and deduction data to external carriers.
• Benefits-to-Payroll Integration: Ensure the seamless integration of Benefit Deductions into Payroll, setting up the necessary Pay Components and mappings to guarantee accurate gross-to-net calculations and compliance (e.g., ACA reporting).

Innovation / Art of Possibility

• Evaluate and shape new project and product requests for strategic fit, technical feasibility, and alignment with enterprise system architecture
• Act as a thought partner to senior leadership and a mentor to HRIS and business analysts, fostering a culture of continuous learning and architectural excellence

Stakeholder Engagement

• Serve as a strategic advisor to People, Total Rewards, Finance, and IT leaders, translating complex business needs into scalable, maintainable Workday solutions
• Partner with stakeholders to define problem statements, assess business impact, and ensure alignment between technology investments and business priorities

Compliance

• Ensure Workday architecture, configurations, and change management processes meet SOX compliance and audit standards, partnering closely with internal audit, InfoSec, and compliance teams
• Champion governance practices across the Workday ecosystem, balancing flexibility with control to enable secure and compliant innovation

What You'll Need to Thrive (Requirements)

• A minimum of ten (10) years of hands-on, expert-level Workday configuration experience.
• At least seven (7) years of deep, primary functional expertise specifically within Workday Benefits and Absence for global companies
• Mandatory: Proven architectural expertise in configuring and managing global Workday Benefits (Plan Setup, Eligibility, Enrollment Events, and Carrier Integrations).
• Mandatory: Proven, hands-on architectural experience managing and expanding global Workday Absence
• A minimum of ten (10) years of demonstrated experience architecting, building, and governing complex Workday security, reporting, and calculated fields within high-risk functional areas
• Proven track record as a Principal Architect/Lead for at least two major global Workday Benefits & Absence programs
• Expert-level knowledge of global labor compliance requirements and how they translate into integrated Workday/CloudPay configuration
• Direct, end-to-end ownership of SOX-compliant programs and processes related to Benefits & Absence programs
• Exceptional executive-level written and verbal communication and negotiation skills, with a proven ability to influence CFO, VP of People, and CIO-level stakeholders on high-risk decisions
• Project management experience with a demonstrated ability to effectively manage several objectives simultaneously while prioritizing and executing technology roadmap plans
• Collaborative problem-solving approach; leverages relationships and strong business acumen to understand not only the “what” the “why” behind requests; displays empathy for partner teams
• Ability to work core EST hours