Aimed at senior HR technology leaders with deep Workday expertise and a track record of scaling People systems in high-demand environments.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Toast
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 Senior Manager, 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)
8+ 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 roadmap experience
Experience leading Workday or People Technology transformation efforts in a high-growth technology company or similarly complex environment
Experience simplifying role-based permissions, security groups, access governance, or audit controls in Workday
Experience with Workday integrations, Workday Extend, Prism, People Analytics, or adjacent reporting tools
Experience implementing AI-enabled features, automation, or workflow intelligence within enterprise SaaS systems
Familiarity with recruiting tools such as GoodTime, BrightHire, sourcing tools, assessment platforms, or background check providers
Experience leading major configuration, implementation, optimization, platform consolidation, or tech debt reduction initiatives
Experience working with distributed or offshore support teams
Why Toast?
This is a meaningful opportunity to shape the future of People Technology at Toast during an important phase of growth and transformation. You will inherit a talented team and a critical platform ecosystem, with the opportunity to bring clarity, structure, innovation, and scale to how Toast supports employees, managers, candidates, and People teams.
In this role, you will lead a mission-critical function, build a strategic roadmap, reduce tech debt, simplify systems experiences, strengthen vendor partnerships, and help Toast get the most value from its People Technology investments.
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 Phil
Source: Toast careers