Head of People Technology

Toast is the all-in-one platform built for restaurants of all sizes. We combine point-of-sale, payments, marketing, payroll, and more into a single platform that helps restaurants simplify operations, increase revenue, and delight guests. At Toast, we are committed to creating an inclusive, high-performing culture where every Toaster can do the best work of their career. As we continue to scale, our People Technology ecosystem plays a critical role in enabling a seamless employee, manager, candidate, and People team experience. Toast is looking for a  Head of People Technology to lead the team responsible for evolving and scaling our People Technology ecosystem, with a primary focus on Workday and a connected focus on recruiting technology, integrations, governance, and experience. You will lead a team responsible for Workday configuration, administration, reporting, security, permissions, business process design, integrations, and support, while also owning the strategy for Greenhouse and the broader TA technology stack in close partnership with Talent Acquisition.  This leader will build a clear Workday and TA technology roadmap, reduce tech debt, improve self-service, simplify permissions, strengthen compliance, and create scalable experiences for employees, managers, candidates, and People teams. You will also identify responsible opportunities to use in-platform AI, automation, and workflow intelligence to improve efficiency and reduce manual work. A critical part of this role will be building strategic partnerships with vendors including Workday, Greenhouse, and other People Technology providers to ensure Toast is using its platforms in best-in-class ways for our size, complexity, and scale. Note:  We are prioritizing candidates located near our hubs in Boston, MA and Toronto, ON.  A day in the life (Responsibilities)  Lead, coach, and develop a high-performing People Technology team responsible for Workday and recruiting technology configuration, administration, security, integrations, reporting, and support Serve as the strategic owner of Workday, including HCM configuration, business process design, reporting, permissions, security, governance, and ongoing optimization Own the strategy for Greenhouse and the broader TA technology stack, ensuring the ecosystem is scalable, integrated, well-governed, and aligned to candidate, recruiter, interviewer, and hiring manager needs  Partner closely with Talent Acquisition Operations to translate recruiting process needs into technology strategy, roadmap priorities, system design, integrations, and adoption plans  Build and manage a clear Workday and TA technology roadmap that balances business priorities, compliance needs, tech debt reduction, stakeholder demand, team capacity, and scalability Reduce tech debt by simplifying processes, improving governance, retiring unnecessary complexity, and driving sustainable system design Improve employee, manager, candidate, and People team self-service through scalable workflows, automation, documentation, intuitive experiences, and change management Simplify and strengthen permissioning, security, access governance, data integrity, SOX readiness, auditability, and controls across Workday, Greenhouse, and connected systems Drive integrations and data flows between Workday, Greenhouse, and adjacent People systems to reduce manual work and improve accuracy Use in-platform AI, automation, and workflow intelligence to responsibly improve efficiency, decision support, case deflection, routing, reporting, and user experience Partner with IT, Security, Legal, Finance, Payroll, TA, People Operations, People Analytics, and People leadership to align technology decisions with business needs and risk requirements Establish intake, prioritization, release, documentation, and change management practices that bring transparency and discipline to a high-demand environment Build strategic vendor partnerships with Workday, Greenhouse, and other People Technology providers to maximize platform value, adopt relevant innovation, and influence vendor roadmaps where appropriate Serve as an escalation point for complex system issues, root cause analysis, and long-term remediation What you'll need to thrive (Requirements) 12+ years of experience in HR technology, People systems, People operations, HRIS, or a related systems-focused role 3+ years of people management experience, with a track record of coaching, developing, and leading high-performing teams Deep Workday experience, including HCM configuration, business processes, reporting, security, permissions, and system governance Experience building or owning a Workday roadmap in a complex, high-demand environment Strong understanding of HR systems integrations, data flows, access controls, reporting, and data integrity practices Experience reducing tech debt, simplifying processes, improving governance, and prioritizing competing stakeholder requests Experience supporting compliance, audit, SOX, or other control requirements within HR systems Familiarity with applicant tracking systems and recruiting technology; Greenhouse experience strongly preferred Experience managing strategic vendor relationships for enterprise HR, Workday, recruiting, or People Technology platforms Ability to evaluate vendor capabilities, platform releases, AI-enabled features, and best-practice recommendations through the lens of business value, compliance, scalability, and user experience Excellent communication and stakeholder management skills, including the ability to translate technical concepts into business impact Strong judgment and prioritization skills, with the ability to balance urgency, risk, capacity, and long-term platform health Nice-to-Have Skills: Workday certifications in HCM, Security, Reporting, Recruiting, Compensation, or related areas Direct Greenhouse administration, configuration, integration, or roa