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.

Toast is a leading cloud-based restaurant and retail management software company based in Boston, Massachusetts. The company provides an all-in-one point of sale system, driven by a commitment to fostering a world-class customer and employee experience, recognized as a key competitive advantage. The People Products team, a strategic arm of the People and Places organization, is dedicated to amplifying this ambition by pioneering AI-powered, conversational, self-service products. These solutions are designed to deliver hyper-personalized employee experiences and actionable workforce intelligence, thereby profoundly enhancing global productivity and engagement.

We are seeking a Principal Workday Architect to serve as a techno-functional Workday PAT expert (70%) and a Benefits configuration expert (30%) and thought partner. This is a highly visible, strategic role that demands a blend of deep technical mastery in Workday and the ability to influence organizational process and technology roadmaps. As a strategic architect and trusted executive-level advisor to the People, Payroll, Finance, IT, and Benefits departments, you will be responsible for configuring and leading the development of robust, scalable, compliant, and impactful Workday solutions that directly drive transformational change in the employee experience and operational efficiency across the enterprise.

A day in the life (Responsibilities)

PAT Global Architecture and Strategic Leadership (70%)

• Act as the definitive global Workday architecture Subject Matter Expert (SME) for global Payroll, Absence, and Time Tracking (PAT). Provide thought leadership and deep technical guidance on these domains, including the optimal architecture for data management between Workday and Cloudpay/external systems.
• Define the multi-year technical roadmap for the Workday PAT ecosystem, ensuring all configurations meet evolving global labor laws and tax regulations.
• Provide strategic, executive-level counsel on Workday capabilities, compliance risks, and technical debt, driving decisions on major global policy changes, country rollouts, and legislative compliance (e.g., FLSA, EMEA/APAC working time directives).

Workday Benefits Architecture and Administration (30%)

• Architect Global Benefits: Own the strategic design and configuration of all Benefit Plans, Plan Types, Coverage Levels, and complex Eligibility Rules across the enterprise, ensuring alignment with global and regional compensation philosophies.
• Lead Enrollment Events: Configure and manage end-to-end Open Enrollment and Life Events/Change Benefits Events, defining workflow rules, validation processes, and 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 the Payroll system, setting up the necessary Pay Components and mappings to guarantee accurate gross-to-net calculations and compliance (e.g., ACA reporting).

Hybrid Global Payroll Integration Architecture

• Lead the End-to-End Design and Expansion of the Workday <> CloudPay Integration: Serve as the primary architect for the Workday-CloudPay connection, utilizing certified frameworks (e.g., Global Payroll Connect) to manage the secure and efficient bi-directional flow of complex time, absence, and payroll data as Toast scales globally.
• Determine the global payroll delivery architecture, defining the criteria for which countries utilize Workday Native Payroll versus the CloudPay integration, optimizing the distribution of PAT functionality (Time, Absence, and Payroll) for each new market.
• Manage Cross-System PAT Data Configuration and Integrity: Own the governance, validation rules, and error-handling protocols for all critical data exchanged between Workday HCM, Time/Absence, and CloudPay, ensuring data consistency and reliability for global payroll execution.
• Lead the design and deployment of the integration for new country rollouts, specifically utilizing certified frameworks like Workday Global Payroll Connect (GPC), Additional Payroll Data (APD), and Data Changes on Demand (DCOD).

Complex Configuration and Compliance Assurance

• Lead the end-to-end configuration and design of the most complex PAT and Benefits processes, including advanced calculation rules for overtime/shift differentials, complex accrual and balance plans, regional/country-specific time policies, and Evidence of Insurability (EOI) rules.
• Establish and enforce rigorous design principles to ensure system stability, data integrity, and seamless integration to minimize pay cycle risk across all payroll methodologies (Workday and CloudPay).
• Partner with Finance and People Operations to redesign and transform complex processes, maximizing automation to achieve a "touchless payroll" environment by designing innovative, future-state Workday solutions.

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 Payroll, Absence, and Time Tracking (PAT).
• Mandatory: Proven architectural expertise in configuring and managing Workday Benefits (Plan Setup, Eligibility, Enrollment Events, and Carrier Integrations).
• Mandatory: Proven, hands-on architectural experience managing and expanding Workday Global Payroll Integrations with a third-party provider (CloudPay experience is a significant advantage).
• 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 payroll implementation programs, managing a complex hybrid payroll environment.
• 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 payroll sign-off, time approvals, system changes, and Benefits deductions in an integrated environment.
• 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 PAT and Benefits decisions.

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.